JPH0763620B2 - Selective photochemical reaction method - Google Patents
Selective photochemical reaction methodInfo
- Publication number
- JPH0763620B2 JPH0763620B2 JP62092746A JP9274687A JPH0763620B2 JP H0763620 B2 JPH0763620 B2 JP H0763620B2 JP 62092746 A JP62092746 A JP 62092746A JP 9274687 A JP9274687 A JP 9274687A JP H0763620 B2 JPH0763620 B2 JP H0763620B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- starting material
- optically active
- active form
- formula
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000006552 photochemical reaction Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 14
- 238000006349 photocyclization reaction Methods 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000009918 complex formation Effects 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 239000013078 crystal Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 150000003952 β-lactams Chemical group 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は光化学変換による合成反応において、生成する
立体異性体の一方を選択的に得るための選択的光化学反
応方法に係り、その目的とする所は化学、薬学の分野で
目的とする化合物を収率良く合成するために有利な方法
を提供するにある。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a selective photochemical reaction method for selectively obtaining one of stereoisomers produced in a synthetic reaction by photochemical conversion, and an object thereof The purpose of the present invention is to provide an advantageous method for synthesizing a desired compound in the fields of chemistry and pharmacy in good yield.
光環化反応において、立体異性体が生成し得る場合に、
この生成比を制御する方法として、出発物質が形成する
結晶格子を利用する方法は良く知られている。例えばケ
イ皮酸誘導体の光環化二量体化において、出発物質の結
晶を光照射することにより選択的に一方の立体異方性を
得ることができる。In the photocyclization reaction, when a stereoisomer can be produced,
As a method for controlling this production ratio, a method using a crystal lattice formed by a starting material is well known. For example, in the photocyclization dimerization of a cinnamic acid derivative, one stereoanisotropy can be selectively obtained by irradiating a crystal of a starting material with light.
しかし、これは極めて特殊な例であって一般的に用いら
れる反応ではない。下記の一般式（Ｉ）で表される化合
物を出発物質１とする光環化反応は次式に従って異性体
２，３，４を生成する。However, this is a very special case and not a commonly used reaction. The photocyclization reaction using the compound represented by the following general formula (I) as a starting material 1 is carried out according to the following formula.
Generate 2 , 3 , and 4 .
（式中Ｒ′はH,CH3,C2H5,C3H7,i−C3H7,又はC6H5,もし
くはＲ′二個として−CH2−Ｘ−CH2−より選ばれる。Ｘ
はCH2,O,−CH2−CH2−より選ばれる。Ｒ″は炭素数15個
以下より成るアルキル基、シクロアルキル基、又は芳香
族基であり、置換基を有しても良い。） この反応は抗生物質において大きい比重を占めるβ−ラ
クタム骨格を合成するための重要な反応であり、従来活
発な研究の対象となっているが、選択性に乏しく、異性
体混合物を与えるにすぎない（JACS.101 5343（197
9），105 1958（1983）,Chem.Commu.333（1983）等参
照）。 (Wherein R 'is H, CH 3, C 2 H 5, C 3 H 7, i-C 3 H 7, or C 6 H 5, or R' -CH 2 -X-CH 2 as two - from Selected X
Is selected from CH 2 , O, —CH 2 —CH 2 —. R ″ is an alkyl group having 15 or less carbon atoms, a cycloalkyl group, or an aromatic group, and may have a substituent.) This reaction synthesizes a β-lactam skeleton occupying a large specific gravity in an antibiotic. Although it is an important reaction for the reaction and has been the subject of active research in the past, it has poor selectivity and only gives an isomer mixture (JACS. 101 5343 (197
9), 105 1958 (1983), Chem. Commu.333 (1983), etc.).
上記光環化反応において、その選択性をコントロールす
ることができれば、目的とする異性体のみを収率よく製
造することができ、煩雑な分離精製の操作も不要とな
り、従って本反応の利用価値ははるかに高いものとなる
ことが期待される。In the above photocyclization reaction, if the selectivity can be controlled, only the desired isomer can be produced in a high yield, and a complicated separation and purification operation is not necessary, and therefore the utility value of this reaction is much higher. It is expected to be very high.
本発明者らは鋭意検討を重ねた結果、上記出発物質１
を、これを有効に抱接し得るホスト化合物との錯体形成
下に光照射を行えば、選択性が著しく向上することを見
出して本発明に到ったものである。 As a result of intensive investigations by the present inventors, the above starting materials1
To form a complex with a host compound that can effectively hug it
We can see that the selectivity is significantly improved by illuminating underneath.
This is the end of the present invention.
即ち、本発明は下記の一般式（Ｉ）で表される出発物質 （式中Ｒ′はH,CH3,C2H5,C3H7,i−C3H7,又はC6H5,もし
くはＲ′二個として−CH2−Ｘ−CH2−より選ばれる。Ｘ
はCH2,O,−CH2−CH2−より選ばれる。Ｒ″は炭素数15個
以下より成るアルキル基、シクロアルキル基、又は芳香
族基であり、置換基を有しても良い。） を下記（II）乃至（Ｖ）式で表される化合物群より選ば
れるホスト化合物との錯体形成下に光照射して上記出発
物質の光環化反応あるいはこれを経て進行する化学変換
を行わせ、生成する異性体のうち一個を選択的に得るこ
とを特徴とする選択的光化学反応方法に関する。That is, the present invention is a starting material represented by the following general formula (I) (Wherein R 'is H, CH 3, C 2 H 5, C 3 H 7, i-C 3 H 7, or C 6 H 5, or R' -CH 2 -X-CH 2 as two - from Selected X
Is selected from CH 2 , O, —CH 2 —CH 2 —. R ″ is an alkyl group having 15 or less carbon atoms, a cycloalkyl group, or an aromatic group, which may have a substituent.) Are represented by the following formulas (II) to (V) The compound is characterized by selectively irradiating one of the produced isomers by irradiating light under complex formation with a host compound selected from the above to cause photocyclization reaction of the above-mentioned starting material or chemical conversion which proceeds through this reaction. To a selective photochemical reaction method.
（式中ＲはC3〜C6より成る環状アルキル基を示す） （式中Ar,Ar′は芳香族基より選ばれ、同一であっても
良い。Ar≠Ar′の場合、（III）はラセミ体であっても
光学活性体であっても良い。 (In the formula, R represents a cyclic alkyl group composed of C 3 to C 6 ) (In the formula, Ar and Ar ′ are selected from aromatic groups and may be the same. When Ar ≠ Ar ′, (III) may be a racemate or an optically active form.
（ラセミ体もしくは光学活性体） （ラセミ体もしくは光学活性体） 本発明の方法を実施する場合、光化学反応の進行が出発
物質１と上記ホスト化合物との相互作用による錯体形成
下に起こることを要するが、両者が結晶性錯体を形成し
ていることが好ましい。このような結晶性錯体は出発物
質１をホスト化合物と共に適切な共通溶媒から再結晶し
て得られる。本発明を実施する一般的な方法としては得
られた結晶を粉砕し、好ましくは時々混ぜることにより
全体に均一に光が当たるようにしながら光照射を行う。
生成物を分離するには蒸留、抽出或いはより親和性の高
いゲスト化合物による置換など、いかなる方法を用いて
も良いが、簡便な方法はそのままクロマトグラフィーに
よる分離を行うことである。 (Racemic or optically active form) (Racemate or Optically Active Form) When the method of the present invention is carried out, it is necessary that the progress of the photochemical reaction occurs under the complex formation due to the interaction between the starting material 1 and the above host compound. It is preferably formed. Such a crystalline complex can be obtained by recrystallizing the starting material 1 together with the host compound from a suitable common solvent. As a general method for carrying out the present invention, the obtained crystals are crushed, and preferably, they are occasionally mixed, and light irradiation is performed while uniformly shining light on the whole.
Any method such as distillation, extraction, or substitution with a guest compound having a higher affinity may be used for separating the product, but a simple method is to perform the separation by chromatography as it is.
本発明に用いるホスト化合物は出発物質１を有効に抱接
し、しかもその光変換を阻害しないものであれば上記化
合物中いかなるものであっても良いが、上記一般式（I
I）で示される化合物（Ｒ＝シクロヘキシル）が好まし
い。The host compound used in the present invention may be any of the above compounds as long as it effectively embraces the starting material 1 and does not inhibit the light conversion thereof.
The compounds represented by I) (R = cyclohexyl) are preferred.
本発明の方法により反応の選択性が高められる理由は完
全に明らかになってはいないが、ホスト化合物に抱接さ
れた状態の出発物質１は分子運動が著しい制約を受けて
おり、一定のコンホメーションをとっているものと考え
られる。また本反応は式にも示すような双極中間体を経
て進行すると推定されているが、この段階においても分
子の回転は制約を受けており、このことが、反応の選択
性を高めているものと推定される。The reason why the selectivity of the reaction is enhanced by the method of the present invention has not been completely clarified, but the starting material 1 in the state of being bound to the host compound is significantly restricted in its molecular motion, and thus it has a certain constancy. It is thought that they are taking a home formation. In addition, this reaction is presumed to proceed via a dipole intermediate as shown in the formula, but the molecular rotation is restricted at this stage as well, which increases the selectivity of the reaction. It is estimated to be.
本発明の方法によれば選択性に異性体のうちの一個を得
ることが出来、しかも少量のホスト化合物があればこれ
を繰り返し使用することもでき、この結果反応の収率を
高め、また操作を簡略化することができる。従って本発
明が化学、薬学の分野における合成技術の向上に貢献す
るところは大きいことが期待される。According to the method of the present invention, one of the isomers can be selectively obtained, and if a small amount of the host compound is present, it can be repeatedly used. As a result, the yield of the reaction can be increased and the operation can be performed. Can be simplified. Therefore, it is expected that the present invention will greatly contribute to the improvement of synthetic techniques in the fields of chemistry and pharmacy.
以下、本発明の方法によってβ−ラクタムの一方の幾何
異性体を選択的に合成する実施例を示すが、本発明がこ
れに限定されるものでないことはいうまでもない。Hereinafter, examples of selectively synthesizing one geometric isomer of β-lactam by the method of the present invention will be shown, but it goes without saying that the present invention is not limited thereto.
表−１に示す化合物1a，1b，1cを各々ホスト化合物（I
I）（一般式（III）において ホスト化合物（III）（一般式（III）においてAr＝Ar′
＝C6H5）との抱接錯体結晶とした。この際、ホスト化合
物（II）を用いる時にはジ−ｎ−プロピルエーテル，ホ
スト化合物（III）を用いる時には石油エーテル−エー
テル混合液を結晶化溶媒とした。次いで、これに高圧水
銀灯の紫外光を照射した。生成物をベンゼン−酢酸エチ
ル混合液を用い、シリカゲルを固定相とするカラムクロ
マトグラフィーによって展開し、未反応の出発物質１，
生成物２，３を分離した。消費された１に対する２，
３，４の収率を表−１に記した。なお、いずれの反応に
おいても五量環生成物４の生成は全く認められなかっ
た。表−１に出発物質、ホスト化合物、抱接錯体結晶の
融点、照射時間、異性体２，３の合計収率、２：３：４
の比を示す。なお、2bの構造は既知サンプルとの比較に
より、2c，3cの立体化学は核磁気共鳴スペクトルの比較
により推定されたが、2aと3a，2bと3bの立体化学は“CH
IRALCEL OC"カラム（ダイセル化学製）での溶出順序を2
c，3cと比較することにより仮定したものである。Compounds 1a , 1b , and 1c shown in Table 1 are each a host compound (I
I) (in the general formula (III) Host compound (III) (in general formula (III), Ar = Ar ′
= C 6 H 5 ). At this time, when the host compound (II) was used, di-n-propyl ether was used, and when the host compound (III) was used, a petroleum ether-ether mixed solution was used as the crystallization solvent. Then, this was irradiated with the ultraviolet light of a high pressure mercury lamp. The product was developed by column chromatography using silica gel as a stationary phase using a benzene-ethyl acetate mixed solution, and the unreacted starting material 1 ,
The products 2 and 3 were separated. 2 for 1 consumed,
The yields of 3 and 4 are shown in Table 1. In any reaction, formation of pentameric ring product 4 was not observed at all. Table 1 shows starting materials, host compounds, melting points of inclusion complex crystals, irradiation time, total yields of isomers 2 and 3 , 2 : 3 : 4
The ratio of The structure of 2b was estimated by comparison with a known sample, and the stereochemistry of 2c and 3c was estimated by comparison of nuclear magnetic resonance spectra. However, the stereochemistry of 2a and 3a , 2b and 3b was
2 elution orders for IRALCEL OC "column (manufactured by Daicel Chemical Industries)
This is assumed by comparing with c and 3c .
Claims (1)
くはＲ′二個として−CH2−Ｘ−CH2−より選ばれる。Ｘ
はCH2,O,−CH2−CH2−より選ばれる。Ｒ″は炭素数15個
以下より成るアルキル基、シクロアルキル基、又は芳香
族基であり、置換基を有しても良い。） を下記（II）乃至（Ｖ）式で表される化合物群より選ば
れるホスト化合物との錯体形成下に光照射して上記出発
物質の光環化反応あるいはこれを経て進行する化学変換
を行わせ、生成する異性体のうち一個を選択的に得るこ
とを特徴とする選択的光化学反応方法。 （式中ＲはC3〜C6より成る環状アルキル基を示す） （式中Ar,Ar′は芳香族基より選ばれ、同一であっても
良い。Ar≠Ar′の場合、（III）はラセミ体であっても
光学活性体であっても良い。） （ラセミ体もしくは光学活性体） （ラセミ体もしくは光学活性体）1. A starting material represented by the following general formula (I): (Wherein R 'is H, CH 3, C 2 H 5, C 3 H 7, i-C 3 H 7, or C 6 H 5, or R' -CH 2 -X-CH 2 as two - from Selected X
Is selected from CH 2 , O, —CH 2 —CH 2 —. R ″ is an alkyl group having 15 or less carbon atoms, a cycloalkyl group, or an aromatic group, which may have a substituent.) Are represented by the following formulas (II) to (V) The compound is characterized by selectively irradiating one of the produced isomers by irradiating light under complex formation with a host compound selected from the above to cause photocyclization reaction of the above-mentioned starting material or chemical conversion which proceeds through this reaction. Selective photochemical reaction method. (In the formula, R represents a cyclic alkyl group composed of C 3 to C 6 ) (In the formula, Ar and Ar 'are selected from an aromatic group and may be the same. When Ar ≠ Ar', (III) may be a racemate or an optically active form.) (Racemic or optically active form) (Racemic or optically active form)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62092746A JPH0763620B2 (en) | 1987-04-15 | 1987-04-15 | Selective photochemical reaction method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62092746A JPH0763620B2 (en) | 1987-04-15 | 1987-04-15 | Selective photochemical reaction method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63258643A JPS63258643A (en) | 1988-10-26 |
| JPH0763620B2 true JPH0763620B2 (en) | 1995-07-12 |
Family
ID=14062979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62092746A Expired - Lifetime JPH0763620B2 (en) | 1987-04-15 | 1987-04-15 | Selective photochemical reaction method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0763620B2 (en) |
-
1987
- 1987-04-15 JP JP62092746A patent/JPH0763620B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63258643A (en) | 1988-10-26 |
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