JPS6049623B2 - Cyclopentanol derivatives and their production method - Google Patents
Cyclopentanol derivatives and their production methodInfo
- Publication number
- JPS6049623B2 JPS6049623B2 JP1563477A JP1563477A JPS6049623B2 JP S6049623 B2 JPS6049623 B2 JP S6049623B2 JP 1563477 A JP1563477 A JP 1563477A JP 1563477 A JP1563477 A JP 1563477A JP S6049623 B2 JPS6049623 B2 JP S6049623B2
- Authority
- JP
- Japan
- Prior art keywords
- cyclopentanol
- methoxycarbonylmethyl
- cis
- production method
- pentenyl
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- XCIXKGXIYUWCLL-HOSYLAQJSA-N cyclopentanol Chemical class O[13CH]1CCCC1 XCIXKGXIYUWCLL-HOSYLAQJSA-N 0.000 title description 2
- XRONOZXFQGVGCK-WAYWQWQTSA-N methyl 2-hydroxy-5-(2-methoxy-2-oxoethyl)-1-[(z)-pent-2-enyl]cyclopentane-1-carboxylate Chemical compound CC\C=C/CC1(C(=O)OC)C(O)CCC1CC(=O)OC XRONOZXFQGVGCK-WAYWQWQTSA-N 0.000 claims 2
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic alcohols Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- VHJDPWYXHODLTH-WAYWQWQTSA-N methyl 3-(2-methoxy-2-oxoethyl)-5-oxo-4-[(z)-pent-2-enyl]cyclopentene-1-carboxylate Chemical compound CC\C=C/CC1C(CC(=O)OC)C=C(C(=O)OC)C1=O VHJDPWYXHODLTH-WAYWQWQTSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は新規なシクロペンタノール誘導体及びその製造
法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel cyclopentanol derivative and a method for producing the same.
本発明の化合物は文献未載の新規化合物てあり、式ＣＨ
２−−ＣＨＣＨ２ＣＯＯＣＨ３
ｌＩ、ＣＨ２ＣＨ二ＣＨＣＨ２ＣＨ３
ＣＨ。The compound of the present invention is a novel compound that has not been described in any literature, and has the formula CH
2--CHCH2COOCH3 lI, CH2CH2CHCH2CH3 CH.
ｃ’＼／ΥＯＯＣＨ３
ＯＨ（Ｉ）
で表わされる２−メトキシカルボニルー３−メトキシカ
ルボニルメチルー２−（シスー２−ベンテニル）−シク
ロペンタノールである。It is 2-methoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-bentenyl)-cyclopentanol represented by c'\/ΥOOCH3 OH(I).
本発明の化合物は植物から入手できる高級香料であるジ
ヤスミン油の主要成分としてよく知られているジヤスモ
ン酸メチルの合成用中間体として有用である。本発明の
化合物は種々の方法により合成されるが、その好ましい
一例を挙げれば式で表才）される５−メトキシカノレボ
ニノレー４−メトキシカルボニルメチルー５−（シスー
２−ペンテニル）−シクロペンテノンを還元することに
より製造される。The compound of the present invention is useful as an intermediate for the synthesis of methyl diasmonate, which is well known as the main component of diasmine oil, which is a high-grade fragrance obtained from plants. The compound of the present invention can be synthesized by various methods, but one preferred example is 5-methoxycanolebonylmethyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-cyclo Produced by reducing pentenone.
本発明に於て出発原料として用いられる式（■）の化合
物は公知の化合物である。The compound of formula (■) used as a starting material in the present invention is a known compound.
上記還元反応に使用される還元剤としては公知のものを
広く使用し得るが、水素化硼素ナトリウム、リチウムト
リ第３級ブトキシアルミニウム等の水素化合物を用いる
のが好ましい。斯かる還元剤の使用量は特に限定がなく
広い範囲で適宜選択されるが、還元剤を式（■）の化合
物に対して０．１〜５倍モル用いるのが望ましい。この
還元反応は通常有機溶媒中て行なわれる。有機溶媒とし
てはメタノール、エタノール、イソプロパノール等の脂
肪族アルコール、テトラヒドロフラン、ジオキサン、エ
チルエーテル等の脂肪族エーテル等を例示できる。該反
応の反応温度は特に限定がなく溶媒の沸点までの広い範
囲内で適宜選択されるが、通常１０〜７０℃、好ましく
は３０〜５０℃である。また反応時間は通常１〜３時間
である。本発明の化合物はｐ過、濃縮、抽出等の慣用手
段を適用することにより容易に精製される。As the reducing agent used in the above reduction reaction, a wide variety of known reducing agents can be used, but it is preferable to use hydrogen compounds such as sodium boron hydride and lithium tri-tert-butoxyaluminum. The amount of the reducing agent to be used is not particularly limited and can be appropriately selected within a wide range, but it is desirable to use the reducing agent in an amount of 0.1 to 5 times the mole of the compound of formula (■). This reduction reaction is usually carried out in an organic solvent. Examples of organic solvents include aliphatic alcohols such as methanol, ethanol, and isopropanol, and aliphatic ethers such as tetrahydrofuran, dioxane, and ethyl ether. The reaction temperature for this reaction is not particularly limited and is appropriately selected within a wide range up to the boiling point of the solvent, but is usually 10 to 70°C, preferably 30 to 50°C. Further, the reaction time is usually 1 to 3 hours. The compounds of the present invention are easily purified by applying conventional means such as filtration, concentration, extraction, etc.
本発明をよソー層明らかにするために以下に実施例を掲
げる。実施例
５−メトキシカルボニルー４−メトキシカルボニルメチ
ルー５−（シスー２−ペンテニル）−２ーシクロペンテ
ノン１．１ｙ及びメタノール２００ｍ１を反応容器に仕
込み、次いで水素化硼素ナトリウム３ｙを加え１時間還
流して反応を行なう。Examples are given below to clearly explain the present invention. Example 5 - 1.1y of methoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone and 200ml of methanol were charged into a reaction vessel, and then 3y of sodium borohydride was added and refluxed for 1 hour. Perform the reaction.
反応混合物を室温に下げ酢酸を少量添加し攪拌を行なう
。約３紛後ガスの発生が終つたらろ過分離し不溶物を除
去する。沖液を減圧下で濃縮しメタノールを留去する。
濃縮残渣を減圧下０．１Ｔｆ＄ＬＨｇで蒸留すれば留分
１１０〜１１５℃である２−メトキシカルボニルー３−
メトキシカルボニルメチルー２−（シスー２−ペンテニ
ル）−シクロペンタノールが無色液体として０．８９ダ
得られる。収率：７９．９％、元素分析値
ＣＨ
実測値（％）６３．４０８．５０
理論値（％）６３．３８８．４５The reaction mixture was cooled to room temperature, a small amount of acetic acid was added, and the mixture was stirred. After about 3 minutes of generation of after-gas, filter and separate to remove insoluble matter. The Oki liquid is concentrated under reduced pressure and methanol is distilled off.
When the concentrated residue is distilled under reduced pressure at 0.1 Tf$LHg, the fraction 2-methoxycarbonyl-3-
0.89 Da of methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol is obtained as a colorless liquid. Yield: 79.9%, elemental analysis value
CH Actual value (%) 63.408.50 Theoretical value (%) 63.388.45
Claims (1)
ルボニルメチル−２−（シス−２−ペンテニル）−シク
ロペンタノール。 ２ 式 ▲数式、化学式、表等があります▼ で表わされる５−メトキシカルボニル−４−メトキシカ
ルボニルメチル−５−（シス−２−ペンテニル）−２−
シクロペンテノンを還元することを特徴とする式▲数式
、化学式、表等があります▼ で表わされる２−メトキシカルボニル−３−メトキシカ
ルボニルメチル−２−（シス−２−ペンテニル）−シク
ロペンタノールの製造法。[Claims] 1 2-Methoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol represented by the formula ▲ Numerical formulas, chemical formulas, tables, etc. are available▼. 2 5-Methoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2- represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
2-methoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol represented by the formula ▲Mathematical formulas, chemical formulas, tables, etc.▼ characterized by reducing cyclopentenone. Manufacturing method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1563477A JPS6049623B2 (en) | 1977-02-15 | 1977-02-15 | Cyclopentanol derivatives and their production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1563477A JPS6049623B2 (en) | 1977-02-15 | 1977-02-15 | Cyclopentanol derivatives and their production method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS53101338A JPS53101338A (en) | 1978-09-04 |
| JPS6049623B2 true JPS6049623B2 (en) | 1985-11-02 |
Family
ID=11894142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1563477A Expired JPS6049623B2 (en) | 1977-02-15 | 1977-02-15 | Cyclopentanol derivatives and their production method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6049623B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7522969B2 (en) | 2004-02-28 | 2009-04-21 | Applied Materials, Inc | Methods and apparatus for material control system interface |
-
1977
- 1977-02-15 JP JP1563477A patent/JPS6049623B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7522969B2 (en) | 2004-02-28 | 2009-04-21 | Applied Materials, Inc | Methods and apparatus for material control system interface |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53101338A (en) | 1978-09-04 |
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