JPS6031813B2 - Cyclopentane derivative, its production method and fragrance composition containing the same - Google Patents
Cyclopentane derivative, its production method and fragrance composition containing the sameInfo
- Publication number
- JPS6031813B2 JPS6031813B2 JP14335877A JP14335877A JPS6031813B2 JP S6031813 B2 JPS6031813 B2 JP S6031813B2 JP 14335877 A JP14335877 A JP 14335877A JP 14335877 A JP14335877 A JP 14335877A JP S6031813 B2 JPS6031813 B2 JP S6031813B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl group
- formula
- represent
- cyclopentane derivative
- cyclopentane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 239000003205 fragrance Substances 0.000 title description 3
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000010948 rhodium Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- 238000007037 hydroformylation reaction Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 239000012437 perfumed product Substances 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001940 cyclopentanes Chemical class 0.000 claims 7
- CXROTAVXRPCAKF-UHFFFAOYSA-N 3-(3-hydroxy-2,3-dimethylcyclopentyl)butanal Chemical compound O=CCC(C)C1CCC(C)(O)C1C CXROTAVXRPCAKF-UHFFFAOYSA-N 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000755716 Convallaria Species 0.000 description 3
- 235000009046 Convallaria majalis Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- FVYXIJYOAGAUQK-UHFFFAOYSA-N honokiol Chemical compound C1=C(CC=C)C(O)=CC=C1C1=CC(CC=C)=CC=C1O FVYXIJYOAGAUQK-UHFFFAOYSA-N 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229940098795 (3z)- 3-hexenyl acetate Drugs 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Natural products CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241000219171 Malpighiales Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NPFVOOAXDOBMCE-PLNGDYQASA-N cis-3-Hexenyl acetate Natural products CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 description 1
- RRGOKSYVAZDNKR-ARJAWSKDSA-M cis-3-hexenylacetate Chemical compound CC\C=C/CCCC([O-])=O RRGOKSYVAZDNKR-ARJAWSKDSA-M 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/06—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
- C07C47/192—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups containing rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は、芳香化学薬品として興味ある、ある種の新規
シクロベンタン誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to certain new cyclobentane derivatives that are of interest as aroma chemicals.
侍磯昭５２−９４２６３号には、下記一般式のシク。Samurai Iso-Sho No. 52-94263 has the following general formula.
へキサン誘導体が記載されている。（式中、ＲＩはアル
キル基を表わし、Ｒ２およびＲ３は各々水素原子あるい
はアルキル基を表わし、そしてＸはヒドロキシ基を表わ
しおよびＹは水素原子を表わし、あるいは×はおよびＹ
は一緒にェポキシ基を表わす。Hexane derivatives are described. (In the formula, RI represents an alkyl group, R2 and R3 each represent a hydrogen atom or an alkyl group, and X represents a hydroxy group and Y represents a hydrogen atom, or
together represent an epoxy group.
）ある種の関連化合物もまた、興味ある芳香性を有する
ことを見し、出した。) Certain related compounds have also been found to have interesting aromatic properties.
それ故、本発明は、下記一般式のシクｏベンタン誘導体
を提供する。Therefore, the present invention provides cyclobentane derivatives of the following general formula.
〔式中、ＲＩおよびＲ４は各々アルキル基を表わし、Ｒ
２およびＲ３は各々水素原子あるいはアルキル基を表わ
す。[In the formula, RI and R4 each represent an alkyl group, and R
2 and R3 each represent a hydrogen atom or an alkyl group.
）Ｒ１，Ｒ２あるいはＲ３がアルキル基を表わす場合、
この基は好ましくは１なし、し４個の炭素原子を有する
アルキル基であり、特にメチルである。) When R1, R2 or R3 represents an alkyl group,
This radical is preferably an alkyl radical having from 1 to 4 carbon atoms, especially methyl.
好ましくは、基Ｒ２およびＲ３のうち１つがアルキルで
ありかつ他のものが水素である。式１の特に好ましい化
合物の例は、３−（２，３−ジメチルー３−ヒドロキシ
シクロベンチル）ブタナールである。Preferably, one of the groups R2 and R3 is alkyl and the other is hydrogen. An example of a particularly preferred compound of formula 1 is 3-(2,3-dimethyl-3-hydroxycyclobentyl)butanal.
本発明は化合物は、下記一般式のオレフィンを金属カル
ボニル触媒の存在下でヒドロホルミル化することを含む
方法により製造され得る。The compounds of the present invention can be prepared by a process comprising hydroformylating an olefin of the general formula below in the presence of a metal carbonyl catalyst.
〔式中、記号Ｒ１、Ｒ２、Ｒ３およびＲ４は前記の意味
を有する。[wherein the symbols R1, R2, R3 and R4 have the above meanings.
）該触媒は、コバルトまたはロジウムカルボニル触媒で
あり得るが、好ましくはロジウム力ルポニル錯体、特に
ヒドラィドおよび／またはホスフィン基をも含む鍔体で
ある。) The catalyst can be a cobalt or rhodium carbonyl catalyst, but is preferably a rhodium carbonyl complex, especially a collared body which also contains hydride and/or phosphine groups.
該触媒は、化合物ＲｈＨ（ＣＯ）〔Ｐ（Ｃ６＆）３〕３
のような同質触媒であり得、あるいは、例えばこのよう
な化合物をシリカのような固体担体上に添加することに
より得られる、異質触媒であり得る。ヒドロホルミル化
の温度は、好ましくは５０ｏ ないし２００００であり
、および一酸化炭素および水素の使用全圧は好ましくは
２００バール以下である。該方法は、有機溶媒例えば脂
肪族、脂環式あるいは芳香族炭化水素中で行なわれ得る
。前記のように、本発明の化合物は、芳香化学薬品とし
て、特に香料（ｐｅｒｆｕｍｅｓ）および例えば石けん
、消臭剤、洗剤およびェアロゾルのような香料添加生成
物に使用するために興味ある化合物である。The catalyst comprises the compound RhH(CO)[P(C6&)3]3
It may be a homogeneous catalyst, such as, or it may be a heterogeneous catalyst, obtained for example by loading such a compound onto a solid support such as silica. The hydroformylation temperature is preferably between 50° and 20,000°C and the total pressure of carbon monoxide and hydrogen used is preferably below 200 bar. The process can be carried out in organic solvents such as aliphatic, cycloaliphatic or aromatic hydrocarbons. As mentioned above, the compounds of the invention are compounds of interest as fragrance chemicals, particularly for use in perfumes and perfumed products such as soaps, deodorants, detergents and aerosols.
本発明を下記の実施例においてさらに説明する。The invention is further illustrated in the following examples.
実施例
ＮＭＲスペクトルが、ジユウテロクロロホルム溶液中６
０ＭＨｚで得られた。Example NMR spectrum in diuterochloroform solution 6
Obtained at 0MHz.
引用した吸収は、テトラメチルシラン基準物質に関し胸
で表わされている。実施例 １
使用したヒドロホルムミル化触媒は、
（Ｃ２＆○）３ＳＩＣ日２Ｃ比Ｐ（Ｃ６日５）２とＲｈ
Ｈ（ＣＯ）〔Ｐ（Ｃ６は）３〕３との予備生成錯体とシ
リカとを反応させることによりつくられ約１．０％Ｗロ
ジウムを含む異質触媒であった。The absorptions quoted are expressed in terms of the tetramethylsilane reference material. Example 1 The hydroformylation catalyst used was (C2&○)3SICday2C ratio P(C6day5)2 and Rh
The heterogeneous catalyst was made by reacting a preformed complex of H(CO)[P(C6 is)3]3 with silica and contained about 1.0% W rhodium.
出発物質は、リナロールを５２５℃で熱分解することに
より製造された２，３ージメチルー１一（１ーメチルー
ビニル）シクロベントー３ーオ−ル（プリノール）の異
性体温合物であった。The starting material was an isomeric compound of 2,3-dimethyl-1-(1-methyl-vinyl)cyclobenthol-3-ol (purinol) produced by pyrolyzing linalool at 525°C.
プリノール混合物（８．０夕）、ヒドロホルミル化触媒
（２．０夕）、ベンゼン（５の‘）およびシクロヘキサ
ン（４０の【）が、１００似のステンレス鋼製オートク
レープ中で混合された。該オートクレーフは、次いで一
酸化炭素と水素との等容量混合物で８０バールに加圧さ
れた。該オートクレープの内容物は、その後１００℃で
４．虫篭間燈拝された。室温まで冷却した後、反応混合
物は炉週および分留された。要求された生成物３一（２
，３−ジメルー３ーヒドロキシシクロベンチル）ブタナ
ールが、収量５．３夕、沸点０．３吻Ｈｇにおいて１０
０〜１０ｙＣで得られた。該生成物のＮＭＲスペクトル
は次の特性吸収を示した。６＝０．７加地（二重線）
）母Ｈ）
６＝０．８功柳（二重線）
６＝０．９花柳（二重線、乳Ｈ）
６＝１．３瓜岬（単線、９Ｈ）
６＝９．８執血（多重線、ＩＨ）
該生成物は、芳香性すずらん（ｍｕ則ｅｔ）臭を有する
。The purinol mixture (8.0 mm), hydroformylation catalyst (2.0 mm), benzene (5'') and cyclohexane (40 mm) were mixed in a 100 mm stainless steel autoclave. The autoclave was then pressurized to 80 bar with an equal volume mixture of carbon monoxide and hydrogen. The contents of the autoclave were then heated at 100° C. 4. He was worshiped by the insect lantern. After cooling to room temperature, the reaction mixture was heated and fractionated. Requested product 3-(2
,3-dimer-3-hydroxycyclobentyl)butanal with a yield of 5.3 min and a boiling point of 0.3 mHg.
Obtained at 0-10yC. The NMR spectrum of the product showed the following characteristic absorptions. 6 = 0.7 Kaji (double line) ) mother H) 6 = 0.8 Koryu (double line) 6 = 0.9 Hanayagi (double line, milk H) 6 = 1.3 Urayu (single line) , 9H) 6=9.8 Blood (multiplet, IH) The product has an aromatic lily of the valley (muet) odor.
実施例 ロ すずらん型の香料組成物が次の処方に従い製造された。Example b A lily of the valley type fragrance composition was produced according to the following recipe.
２０の重量部 シトロネロール１５０ 〃 ヒドロキシ
シトロネラール
１００ 〃 リナロール
５０ 〃 リナリルアセテート
５０ 〃 べ−夕−フ工二ルーエタノール５０ ″ ア
ルフアーヨノン十
３０ 〃 シトロネリルアセテート
３０ ″ テルピネオール
３０ 〃 ４一（トリシクロ５．２．１．１．２，６デ
シリド−８ーエン）−ブタナール十２０ 〃 ペンジル
アセテート
２の重量部 ２−メチル−３−（ｐ−第３級ブチルフエ
ニル）ープロパナール２０ 〃 アルフアーベンチルー
シンナムアルデトヒド２０ 〃 インドール＋１０ 〃
シンナミルアルコール
１０ 〃 アセトアルデヒドエチルリナルアセターノレ
＋１０ 〃 シス３一ヘキセニルアセテート＋８００
重量部十）ジヱチレングリコールレモノエチ
ルェーテル中１０％溶液
この組成物は、容認できるすずらん臭を有していた。20 parts by weight Citronellol 150 〃 Hydroxycitronellal 100 〃 Linalool 50 〃 Linalyl acetate 50 〃 Base-based diluent ethanol 50 ″ Alphayoone 130 〃 Citronellyl acetate 30 ″ Terpineol 30 〃 41 (Tricyclo 5.2 .1.1.2,6 desylide-8-ene)-butanal 120 parts by weight of penzyl acetate 2 2-methyl-3-(p-tert-butylphenyl)-propanal 20 alpha-benzyl cinnamaldetohyde 20 〃 Indole +10 〃
Cinnamyl alcohol 10 〃 Acetaldehyde ethyl linal acetate + 10 〃 Cis-3-hexenyl acetate + 800
Parts by Weight 10% Diethylene Glycol Lemonoethyl Ether 10% Solution This composition had an acceptable lily of the valley odor.
Claims (1)
、並びにＲ＾２およびＲ＾３は各々水素原子あるいはア
ルキル基を表わす〕のシクロペンタン誘導体。 ２ 基Ｒ＾２およびＲ＾３のうち１つがアルキルであり
、かつ他が水素である特許請求の範囲第１項に記載のシ
クロペンタン誘導体。 ３ アルキル基が、１ないし４個の炭素原子を有するも
のである特許請求の範囲第１項あるいは第２項に記載の
シクロペンタン誘導体。 ４ ３−（２，３−ジメチル−３−ヒドロキシシクロペ
ンチル）ブタナールである特許請求の範囲第１項に記載
のシクロペンタン誘導体。 ５ 一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＾１およびＲ＾４は各々アルキル基を表わし
、並びにＲ＾２およびＲ＾３は各々水素原子あるいはア
ルキル基を表わす〕のシクロペンタン誘導体の製造法に
おいて、一般式、▲数式、化学式、表等があります▼ 〔式中、記号Ｒ＾１、Ｒ＾２，Ｒ＾３およびＲ＾４は上
記に記載の意味を有する〕のオレフイン金属カルボニル
触媒の存在下でヒドロホルミル化することを特徴とする
上記シクロペンタン誘導体の製造法。 ６ 触媒がロジウムカルボニル錯体である特許請求の範
囲第５項に記載の方法。 ７ ロジウムカルボニル錯体がヒドライドおよび／また
はホスフイン基を含む特許請求の範囲第６項に記載の方
法。 ８ 触媒が化合物ＲｈＨ（ＣＯ）〔Ｐ（Ｃ＿６Ｈ＿５）
＿３〕＿３である特許請求の範囲第５項ないし第７項の
いずれか１項に記載の方法。 ９ 一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒ＾１およびＲ＾４は各々アルキル基を表わし
、並びにＲ＾２およびＲ＾３は各々水素原子あるいはア
ルキル基を表わす〕のシクロペンタン誘導体を含む、香
料組成物あるいは香料添加生成物。[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R^1 and R^4 each represent an alkyl group, and R^2 and R^3 each represent a hydrogen atom or cyclopentane derivative of ] representing an alkyl group. 2. The cyclopentane derivative according to claim 1, wherein one of the groups R^2 and R^3 is alkyl and the other is hydrogen. 3. The cyclopentane derivative according to claim 1 or 2, wherein the alkyl group has 1 to 4 carbon atoms. 4. The cyclopentane derivative according to claim 1, which is 3-(2,3-dimethyl-3-hydroxycyclopentyl)butanal. 5 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 and R^4 each represent an alkyl group, and R^2 and R^3 each represent a hydrogen atom or an alkyl group] In the production method of cyclopentane derivatives, there are general formulas, ▲mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, the symbols R^1, R^2, R^3 and R^4 have the meanings described above] A method for producing the above-mentioned cyclopentane derivative, comprising hydroformylation in the presence of an olefin metal carbonyl catalyst. 6. The method according to claim 5, wherein the catalyst is a rhodium carbonyl complex. 7. The method according to claim 6, wherein the rhodium carbonyl complex contains a hydride and/or phosphine group. 8 The catalyst is the compound RhH(CO) [P(C_6H_5)
_3]_3 The method according to any one of claims 5 to 7. 9 General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R^1 and R^4 each represent an alkyl group, and R^2 and R^3 each represent a hydrogen atom or an alkyl group] A perfume composition or perfumed product comprising a cyclopentane derivative.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5050576A GB1550004A (en) | 1976-12-03 | 1976-12-03 | Cyclopentane derivatives |
| GB50505/1976 | 1976-12-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5371039A JPS5371039A (en) | 1978-06-24 |
| JPS6031813B2 true JPS6031813B2 (en) | 1985-07-24 |
Family
ID=10456151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14335877A Expired JPS6031813B2 (en) | 1976-12-03 | 1977-12-01 | Cyclopentane derivative, its production method and fragrance composition containing the same |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS6031813B2 (en) |
| CH (1) | CH631148A5 (en) |
| DE (1) | DE2753644C2 (en) |
| FR (1) | FR2372784A1 (en) |
| GB (1) | GB1550004A (en) |
| NL (1) | NL7713270A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0379714U (en) * | 1989-12-08 | 1991-08-14 | ||
| JPH0431000U (en) * | 1990-07-11 | 1992-03-12 | ||
| US12011008B2 (en) | 2016-06-06 | 2024-06-18 | Brain Brew Ventures 3.0, Inc. | Method for creating smoked foods and beverages |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2837480A1 (en) * | 1978-08-28 | 1980-03-20 | Ruhrchemie Ag | METHOD FOR PRODUCING 3- (4-METHYL-3-CYCLOHEXEN-L-YL) BUTYRALDEHYDE |
| ES2167829T3 (en) | 1997-11-11 | 2002-05-16 | Firmenich & Cie | NITRILS AND ALDEHIDS DERIVED FROM 3-ISOPROPENYL-1,2-DIMETHYL-1-CYCLOPENTANOL AND ITS USE IN PERFUMERIA. |
-
1976
- 1976-12-03 GB GB5050576A patent/GB1550004A/en not_active Expired
-
1977
- 1977-11-30 FR FR7736105A patent/FR2372784A1/en active Granted
- 1977-12-01 NL NL7713270A patent/NL7713270A/en not_active Application Discontinuation
- 1977-12-01 DE DE19772753644 patent/DE2753644C2/en not_active Expired
- 1977-12-01 JP JP14335877A patent/JPS6031813B2/en not_active Expired
- 1977-12-01 CH CH1472277A patent/CH631148A5/en not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0379714U (en) * | 1989-12-08 | 1991-08-14 | ||
| JPH0431000U (en) * | 1990-07-11 | 1992-03-12 | ||
| US12011008B2 (en) | 2016-06-06 | 2024-06-18 | Brain Brew Ventures 3.0, Inc. | Method for creating smoked foods and beverages |
| US12295380B2 (en) | 2016-06-06 | 2025-05-13 | Brain Brew Ventures 3.0, Inc. | Method for creating smoked foods and beverages |
Also Published As
| Publication number | Publication date |
|---|---|
| CH631148A5 (en) | 1982-07-30 |
| DE2753644A1 (en) | 1978-06-08 |
| FR2372784A1 (en) | 1978-06-30 |
| NL7713270A (en) | 1978-06-06 |
| FR2372784B1 (en) | 1981-01-09 |
| GB1550004A (en) | 1979-08-08 |
| DE2753644C2 (en) | 1986-09-25 |
| JPS5371039A (en) | 1978-06-24 |
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