JPH0739407B2 - 3-phenylthio-2- (1'-hydroxy-1'-substituted methyl) -4-pentanolides and process for producing the same - Google Patents
3-phenylthio-2- (1'-hydroxy-1'-substituted methyl) -4-pentanolides and process for producing the sameInfo
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- JPH0739407B2 JPH0739407B2 JP12922286A JP12922286A JPH0739407B2 JP H0739407 B2 JPH0739407 B2 JP H0739407B2 JP 12922286 A JP12922286 A JP 12922286A JP 12922286 A JP12922286 A JP 12922286A JP H0739407 B2 JPH0739407 B2 JP H0739407B2
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- hydroxy
- phenylthio
- formula
- substituted methyl
- pentanolide
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Description
【発明の詳細な説明】 産業上の利用分野 本発明は新規な３−フエニルチオ−２−（１′−ヒドロ
キシ−１′−置換メチル）−４−ペンタノリド類、殊に
その光学異性体類、及びそれ等の製法に関する。本発明
の新規な３−フエニルチオ−２−（１′−ヒドロキシ−
１′−置換メチル）−４−ペンタノリド類は医薬分野、
農園芸分野などにおいて抗菌、殺菌、殺虫剤などとして
有用な生理活性化合物又はその中間体として有用であ
る。The present invention relates to novel 3-phenylthio-2- (1'-hydroxy-1'-substituted methyl) -4-pentanolides, in particular their optical isomers, and Regarding the manufacturing method of them. The novel 3-phenylthio-2- (1'-hydroxy-) of the present invention
1′-substituted methyl) -4-pentanolides are used in the field of medicine,
It is useful as a physiologically active compound useful as an antibacterial agent, a bactericidal agent, an insecticide, etc., or an intermediate thereof in the fields of agriculture and horticulture.
本発明の特徴 本発明者らは、例えば医薬分野、農薬芸分野などにおい
て抗菌、殺菌、殺虫剤などとして有用な生理活性化合
物、更にはその合成中間体として有用な３−フエニルチ
オ−２−ブテン−４−オリド系化合物の合成研究を行つ
てきたが、今回、新規な３−フエニルチオ−２−（１′
−ヒドロキシ−１′−置換メチル）−４−ペンタノリド
類及びその光学異性体が存在できること並びにそれらの
化合物が容易な手段で合成できることを発見した。Features of the Invention The present inventors have found that, for example, in the fields of medicine, agrochemicals, etc., physiologically active compounds useful as antibacterial agents, germicides, insecticides, and 3-phenylthio-2-butene-useful as synthetic intermediates thereof. We have been conducting research on the synthesis of 4-olid compounds, but this time, we have developed a novel 3-phenylthio-2- (1 '
It has been discovered that -hydroxy-1'-substituted methyl) -4-pentanolides and their optical isomers can exist and that these compounds can be synthesized by facile means.
本発明によれば式 〔こゝで、Ｒはハロゲン及び低級アルキル基によりなる
群より選ばれた置換基を随意有してもよいフエニル基も
しくはベンジル基、又はＣ１〜Ｃ10のアルキル基を示
す〕 の新規なる３−フエニルチオ−２−（１′−ヒドロキシ
−１′−置換メチル）−４−ペンタノリド類が提供され
る。According to the invention the formula [Wherein R represents a phenyl group or a benzyl group which may optionally have a substituent selected from the group consisting of halogen and a lower alkyl group, or a C 1 -C 10 alkyl group]. -Phenylthio-2- (1'-hydroxy-1'-substituted methyl) -4-pentanolides are provided.
本発明によれば、更に式（Ｉ）の化合物の光学異性体で
ある式 〔こゝでＲは前記の意味を有する〕 の新規な２−（Ｓ）−〔１′−（Ｓ）−ヒドロキシ−
１′−置換メチル〕−３−（Ｒ）−フエニルチオ−４−
（Ｓ）−ペンタノリド、式 〔こゝでＲは前記の意味を有する〕 の新規な２−（Ｓ）−〔１′−（Ｒ）−ヒドロキシ−
１′−置換メチル〕−３−（Ｒ）−フエニルチオ−４−
（Ｓ）−ペンタノリド、式 〔こゝでＲは、前記の意味を有する〕 の新規な２−（Ｒ）−〔１′−（Ｓ）−ヒドロキシ−
１′−置換メチル〕−３−（Ｒ）−フエニルチオ−４−
（Ｓ）−ペンタノリド及び式 〔こゝでＲは前記の意味を有する〕 の新規な２−（Ｒ）−〔１′−（Ｒ）−ヒドロキシ−
１′−置換メチル〕−３−（Ｒ）−フエニルチオ−４−
（Ｓ）−ペンタノリドが提供される。According to the invention, there is further provided the formula which is an optical isomer of a compound of formula (I) A novel 2- (S)-[1 '-(S) -hydroxy-, wherein R has the above-mentioned meaning.
1'-Substituted methyl] -3- (R) -phenylthio-4-
(S) -pentanolide, formula A new 2- (S)-[1 '-(R) -hydroxy-] of [wherein R has the above meaning]
1'-Substituted methyl] -3- (R) -phenylthio-4-
(S) -pentanolide, formula [Wherein R has the above-mentioned meaning] and new 2- (R)-[1 '-(S) -hydroxy-
1'-Substituted methyl] -3- (R) -phenylthio-4-
(S) -pentanolide and formula A novel 2- (R)-[1 '-(R) -hydroxy-] of [wherein R has the above-mentioned meaning]
1'-Substituted methyl] -3- (R) -phenylthio-4-
(S) -Pentanolide is provided.
上記式（Ｉ）、（I a）、（I b）、（I c）、及び（I
d）の置換基Ｒの定義における「ハロゲン」としては塩
素、臭素、弗素などのようなハロゲン原子を例示するこ
とができ、「低級アルキル基」としては、メチル、エチ
ル、ｎ−プロピル、iso−プロピル、ｎ−ブチル、iso−
ブチル、sec−ブチル、tert−ブチルを例示することが
できる。また「Ｃ１〜Ｃ10のアルキル基」としては、メ
チル、エチル、ｎ−プロピル、iso−プロピル、ｎ−ブ
チル、iso−ブチル、sec−ブチル、tert−ブチル、ｎ−
ペンチル、iso−ペンチル、ｎ−ヘキシル、iso−ヘキシ
ル、ｎ−ヘプチル、iso−ヘプチル、ｎ−オクチル、iso
−オクチル、ノニル、デシルを例示することができる。Formulas (I), (Ia), (Ib), (Ic), and (I
Examples of “halogen” in the definition of the substituent R of d) include halogen atoms such as chlorine, bromine, fluorine, etc., and examples of the “lower alkyl group” include methyl, ethyl, n-propyl, iso- Propyl, n-butyl, iso-
Butyl, sec-butyl, and tert-butyl can be exemplified. In addition, examples of the "C 1 -C 10 alkyl group" include methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-.
Pentyl, iso-pentyl, n-hexyl, iso-hexyl, n-heptyl, iso-heptyl, n-octyl, iso
Examples thereof include octyl, nonyl and decyl.
式 〔こゝで、Ｒは前記の意味を有する〕 の３−フエニルチオ−２−（１′−ヒドロキシ−１′−
置換メチル）−４−ペンタノリド類は式 のβ−アンゲリカラクトン（γ−メチル−α，βークロ
トノラクトン）を、式 Ｒ−CHO （III） 〔こゝで、Ｒは上記の意味を有する〕 のアルデヒド及び式 のリチウム・チオフエノキシドと同時に反応させること
によつて得ることができる。formula [Herein, R has the above-mentioned meaning] 3-phenylthio-2- (1'-hydroxy-1'-
Substituted methyl) -4-pentanolides have the formula Of β-angelica lactone (γ-methyl-α, β-crotonolactone) of formula R-CHO (III) [wherein R has the above meaning] and a formula Can be obtained by reacting with lithium thiophenoxide at the same time.
上記反応は下記反応式によつて示すことができる。The above reaction can be shown by the following reaction formula.
式（I a）、（I b）、（I c）及び（I d）の光学異性体
は、上記のようにして生成した式（Ｉ）の３−フエニル
チオ−２−（１′−ヒドロキシ−１′−置換メチル）−
４−ペンタノリド類を光学分割することにより容易に得
ることができる。 The optical isomers of formulas (Ia), (Ib), (Ic) and (Id) are the 3-phenylthio-2- (1'-hydroxy-)-formulas of formula (I) produced as described above. 1'-substituted methyl)-
It can be easily obtained by optically resolving 4-pentanolides.
式（II）の化合物と式（III）の化合物及び式（IV）の
化合物との反応は、好ましくは不活性ガス（例えば窒
素、アルゴンなど）雰囲気下に、例えばチオフエノール
をTHFに溶解し、これにｎ−ブチルリチウム・ヘキサン
溶液を加え、式（IV）の化合物を生成せしめ、この溶液
を−50℃に冷却し、これに式（II）の化合物β−アンゲ
リカラクトンと式（III）の化合物ベンズアルデヒドのT
HF混合溶液を加え、−50℃で反応を行う。反応終了後、
反応液を飽和塩化アンモニウム溶液で処理し、ジクロロ
メタンで抽出した後、無水硫酸マグネシウムで脱水乾燥
し、溶媒を除去する。式（Ｉ）の化合物が残留物として
取得される。この残留物をシリカゲル−カラムクロマト
グラフイーで石油エーテル・エーテル（5:1）混合溶媒
を用い分離精製すれば、先づ（I c）が溶出し、次いで
（I d）と（I a）の混合物が溶出し、第三に（I b）が
溶出する。（I d）と（I a）との混合物は再度シリカゲ
ル・カラムクロマトグラフイーを用い、ベンゼン・ジク
ロロメタン（1:1）の混合溶媒にて分離を行えば、先づ
（I d）が溶出し、次いで（I a）が溶出し分離される。The reaction of the compound of the formula (II) with the compound of the formula (III) and the compound of the formula (IV) is preferably carried out by dissolving, for example, thiophenol in THF under an atmosphere of an inert gas (such as nitrogen or argon), A solution of n-butyllithium / hexane is added thereto to form a compound of formula (IV), and the solution is cooled to -50 ° C., to which the compound β-angelicalactone of formula (II) and the compound of formula (III) are added. Compound T of benzaldehyde
Add the HF mixed solution and carry out the reaction at -50 ° C. After the reaction,
The reaction solution is treated with a saturated ammonium chloride solution, extracted with dichloromethane, dried over anhydrous magnesium sulfate and dried to remove the solvent. The compound of formula (I) is obtained as a residue. This residue was separated and purified by silica gel-column chromatography using a petroleum ether / ether (5: 1) mixed solvent to elute (I c) first, and then (I d) and (I a) The mixture elutes and thirdly (I b) elutes. If the mixture of (I d) and (I a) is again subjected to silica gel column chromatography and separated with a mixed solvent of benzene and dichloromethane (1: 1), (I d) will be eluted first. , Then (I a) is eluted and separated.
上記反応に於て、不活性ガスとしては例えば窒素、アル
ゴンの如き不活性ガスを例示することができる。In the above-mentioned reaction, examples of the inert gas include inert gases such as nitrogen and argon.
出発化合物である式（II）のβ−アンゲリカラクトンは
既知の化合物であつて、例えば、文献:K.IWAI et.al.C
hem.Lett.,385 （1974）に記載された製法により製造することができ
る。該文献記載の製法を反応式で示すと下記のようにな
る： 即ち、文献（VII）のチオフエキノシ酢酸とプロピレン
オキシドとをテトラヒドロフラン（THF）溶媒中で、リ
チウム・ジイソプロピルアミド（LDA）存在下に反応せ
しめて、式（VI）の化合物を合成し、これを過沃素酸ナ
トリウムで酸化して、式（Ｖ）のスルオキシド化合物と
した後、トルエン溶媒中で熱分解すれば上記式（II）の
β−アンゲリカラクトンが容易に製造し得られる。The starting compound, β-angelica lactone of formula (II), is a known compound, for example, reference: K.IWAI et.al.C.
It can be produced by the production method described in hem. Lett., 385 (1974). The reaction scheme of the production method described in the literature is as follows: That is, thiophenequinoxyacetic acid of Reference (VII) and propylene oxide were reacted in a solvent of tetrahydrofuran (THF) in the presence of lithium diisopropylamide (LDA) to synthesize a compound of formula (VI), The β-angelicalactone of the above formula (II) can be easily produced by oxidizing with sodium acidate to obtain the sulfoxide compound of the formula (V) and then thermally decomposing it in a toluene solvent.
本発明の効果 本発明は新規な３−フエニルチオ−２−（１′−ヒドロ
キシ−１′−置換メチル）−４−ペンタノリド類とその
光学異性体類及びそれ等の製法を提供するもので、本発
明による３−フエニルチオ−２−（１′−ヒドロキシ−
１′−置換メチル）−４−ペンタノリド類、殊にその光
学異性体類は医薬分野、農園芸分野などにおいて抗菌、
殺菌、殺虫剤などとして有用な生理活性化合物又はその
中間体であり、本発明は該分野の技術の進歩に大きく貢
献するものである。EFFECTS OF THE INVENTION The present invention provides novel 3-phenylthio-2- (1′-hydroxy-1′-substituted methyl) -4-pentanolides and their optical isomers and a process for producing them. According to the invention 3-phenylthio-2- (1'-hydroxy-
1'-substituted methyl) -4-pentanolides, especially optical isomers thereof, are antibacterial in the fields of medicine, agriculture and horticulture, etc.
The present invention is a physiologically active compound useful as a sterilizer, an insecticide or the like, or an intermediate thereof, and the present invention greatly contributes to the progress of the technology in the field.
実 施 例 不活性ガス雰囲気下で、チオフエノール1.10g（10ミリ
モル）をTHF5mlに溶解し、これを冷却した後、1.7M ｎ
−ブチルリチウム・ヘキサン溶液5.88ml（10ミリモル）
を加え、10分間攪拌してリチウム・チオフエノキシドを
生成せしめる。この溶液に、β−アンゲリカラクトン0.
980g（10ミリモル）とベンズアルデヒド1.27g（12ミニ
モル）をTHF8mlに溶解した混合溶液を一度に添加し、−
50℃で15分間攪拌して反応を行う。反応終了後、反応液
に飽和塩化アンモニウム水溶液15mlを加えて、よく攪拌
した後、50mlのジクロロメタンで３回抽出を行い、ジク
ロロメタン層を無水硫酸マグネシウムで脱水乾燥する。
次に溶媒を留去する。残留物をシリカゲル・カラムクロ
マトグラフイーで石油エーテル・エーテル（5:1）混合
溶媒を用い分離精製する。先づ下記表１の（I c′）0.5
3g、（収率;17％）が溶出し、次いで（I a′）及び（I
d′）が混合物として2.1gが得られた。最後に（I b′）
が溶出し、0.50g、（収率16％）が得られた。（I a′）
と（I d′）との混合物は再度シリカゲル・カラムクロ
マトグラフイーにより、ベンゼン・ジクロロメタン（1:
1）混合溶媒で分離精製すると先づ（I d′）が溶出し、
0.97g（収液;31％）が得られた。次いで（I a′）が溶
出し、1.13g（収液;36％）が得られた。Practical example 1.10 g (10 mmol) of thiophenol was dissolved in 5 ml of THF under an inert gas atmosphere, and after cooling this, 1.7 M n
-Butyl lithium-hexane solution 5.88 ml (10 mmol)
Is added and stirred for 10 minutes to generate lithium thiophene oxide. To this solution was added β-angelica lactone.
A mixed solution of 980 g (10 mmol) and benzaldehyde (1.27 g, 12 minimol) dissolved in 8 ml of THF was added at once,
The reaction is carried out by stirring at 50 ° C for 15 minutes. After completion of the reaction, 15 ml of a saturated aqueous solution of ammonium chloride is added to the reaction solution, and after stirring well, extraction is performed 3 times with 50 ml of dichloromethane, and the dichloromethane layer is dehydrated and dried with anhydrous magnesium sulfate.
Then the solvent is distilled off. The residue is separated and purified by silica gel column chromatography using a petroleum ether / ether (5: 1) mixed solvent. First, (I c ′) 0.5 in Table 1 below.
3 g, (yield; 17%) were eluted, followed by (I a ′) and (I
2.1 g of d ') was obtained as a mixture. Finally (I b ′)
Was eluted, and 0.50 g (yield 16%) was obtained. (I a ′)
The mixture of and (I d ′) was again subjected to silica gel column chromatography, and benzene-dichloromethane (1:
1) When separated and purified with a mixed solvent, (I d ′) elutes first,
0.97 g (collected liquid; 31%) was obtained. Next, (Ia ') was eluted, and 1.13 g (collected liquid; 36%) was obtained.
その物理的データを表１に示した。The physical data are shown in Table 1.
Claims (10)
より選ばれた置換基を随意有してもよいフエニル基もし
くはベンジル基、又はＣ１〜Ｃ10のアルキル基を示す〕 の３−フエニルチオ−２−（１′−ヒドロキシ−１′−
置換メチル）−４−ペンタノリド類。1. A formula [Wherein R represents a phenyl group or a benzyl group which may optionally have a substituent selected from the group consisting of halogen and a lower alkyl group, or a C 1 -C 10 alkyl group]. -2- (1'-hydroxy-1'-
Substituted methyl) -4-pentanolides.
る〕 の２−（Ｓ）−〔１′−（Ｓ）−ヒドロキシ−１′−置
換メチル〕−３−（Ｒ）−フエニルチオ−４−（Ｓ）−
ペンタノリドである特許請求の範囲第１項記載の３−フ
エニルチオ−２−（１′−ヒドロキシ−１′−置換メチ
ル）−４−ペンタノリド類。2. A formula 2- (S)-[1 '-(S) -hydroxy-1'-substituted methyl] -3- (R) -phenylthio of [wherein R has the meaning defined in claim 1] -4- (S)-
A 3-phenylthio-2- (1'-hydroxy-1'-substituted methyl) -4-pentanolide according to claim 1, which is pentanolide.
る〕 の２−（Ｓ）−〔１′−（Ｒ）−ヒドロキシ−１′−置
換メチル〕−３−（Ｒ）−フエニルチオ−４−（Ｓ）−
ペンタノリドである特許請求の範囲第１項記載の３−フ
エニルチオ−２−（１′−ヒドロキシ−１′−置換メチ
ル）−４−ペンタノリド類。3. A formula 2- (S)-[1 '-(R) -hydroxy-1'-substituted methyl] -3- (R) -of [wherein R has the meaning defined in claim 1] Phenylthio-4- (S)-
A 3-phenylthio-2- (1'-hydroxy-1'-substituted methyl) -4-pentanolide according to claim 1, which is pentanolide.
する〕 の２−（Ｒ）−〔１′−（Ｓ）−ヒドロキシ−１′−置
換メチル〕−３−（Ｒ）−フエニルチオ−４−（Ｓ）−
ペンタノリドである特許請求の範囲第１項記載の３−フ
エニルチオ−２−（１′−ヒドロキシ−１′−置換メチ
ル）−４−ペンタノリド類。4. A formula 2- (R)-[1 '-(S) -hydroxy-1'-substituted methyl] -3- (R) of [wherein R has the meaning defined in claim 1] -Phenylthio-4- (S)-
A 3-phenylthio-2- (1'-hydroxy-1'-substituted methyl) -4-pentanolide according to claim 1, which is pentanolide.
る〕 の２−（Ｒ）−〔１′−（Ｒ）−ヒドロキシ−１′−置
換メチル〕−３−（Ｒ）−フエニルチオ−４−（Ｓ）−
ペンタノリドである特許請求の範囲第１項記載の３−フ
エニルチオ−２−（１′−ヒドロキシ−１′−置換メチ
ル）−４−ペンタノリド類。5. A formula [Wherein R has the meaning defined in claim 1] 2- (R)-[1 '-(R) -hydroxy-1'-substituted methyl] -3- (R)- Phenylthio-4- (S)-
A 3-phenylthio-2- (1'-hydroxy-1'-substituted methyl) -4-pentanolide according to claim 1, which is pentanolide.
より選ばれた置換基を随意有してもよいフエニル基もし
くはベンジル基、又はＣ１〜Ｃ10のアルキル基を示す〕 の３−フエニルチオ−２−（１′−ヒドロキシ−１′−
置換メチル）−４−ペンタノリド類の目的化合物を製造
するにあたり、式 のβ−アンゲリカラクトンを、式 Ｒ−CHO （III） 〔こゝで、Ｒは上記の意味を有する〕 のアルデヒド及び式 のリチウム・チオフエノキシドと反応させることを特徴
とする製法。6. A formula [Wherein R represents a phenyl group or a benzyl group which may optionally have a substituent selected from the group consisting of halogen and a lower alkyl group, or a C 1 -C 10 alkyl group]. -2- (1'-hydroxy-1'-
In producing the target compound of the substituted methyl) -4-pentanolides, Β-angelica lactone of the formula R-CHO (III) [wherein R has the above meaning] and a formula The reaction method is characterized by reacting with lithium thiophene oxide.
る〕 の２−（Ｓ）−〔１′−（Ｓ）−ヒドロキシ−１′−置
換メチル〕−３−（Ｒ）−フエニルチオ−４−（Ｓ）−
ペンタノリドである特許請求の範囲第６項記載の製法。7. The target compound is of the formula 2- (S)-[1 '-(S) -hydroxy-1'-substituted methyl] -3- (R) -phenylthio of [wherein R has the meaning defined in claim 6] -4- (S)-
The method according to claim 6, which is pentanolide.
る〕 の２−（Ｓ）−〔１′−（Ｒ）−ヒドロキシ−１′−置
換メチル〕−３−（Ｒ）−フエニルチオ−４−（Ｓ）−
ペンタノリドである特許請求の範囲第６項記載の製法。8. The target compound is of the formula 2- (S)-[1 '-(R) -hydroxy-1'-substituted methyl] -3- (R) -phenylthio of [wherein R has the meaning described in claim 6] -4- (S)-
The method according to claim 6, which is pentanolide.
する〕 の２−（Ｒ）−〔１′−（Ｓ）−ヒドロキシ−１′−置
換メチル〕−３−（Ｒ）−フエニルチオ−４−（Ｓ）−
ペンタノリドである特許請求の範囲第６項記載の製法。9. The target compound is of the formula 2- (R)-[1 '-(S) -hydroxy-1'-substituted methyl] -3- (R) of [wherein R has the meaning defined in claim 6] -Phenylthio-4- (S)-
The method according to claim 6, which is pentanolide.
る〕 の２−（Ｒ）−〔１′−（Ｒ）−ヒドロキシ−１′−置
換メチル〕−３−（Ｒ）−フエニルチオ−４−（Ｓ）−
ペンタノリドである特許請求の範囲第６項記載の製法。10. The target compound is of the formula [Wherein R has the meaning defined in claim 6] 2- (R)-[1 '-(R) -hydroxy-1'-substituted methyl] -3- (R)- Phenylthio-4- (S)-
The method according to claim 6, which is pentanolide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12922286A JPH0739407B2 (en) | 1986-06-05 | 1986-06-05 | 3-phenylthio-2- (1'-hydroxy-1'-substituted methyl) -4-pentanolides and process for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12922286A JPH0739407B2 (en) | 1986-06-05 | 1986-06-05 | 3-phenylthio-2- (1'-hydroxy-1'-substituted methyl) -4-pentanolides and process for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62286984A JPS62286984A (en) | 1987-12-12 |
| JPH0739407B2 true JPH0739407B2 (en) | 1995-05-01 |
Family
ID=15004164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12922286A Expired - Lifetime JPH0739407B2 (en) | 1986-06-05 | 1986-06-05 | 3-phenylthio-2- (1'-hydroxy-1'-substituted methyl) -4-pentanolides and process for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0739407B2 (en) |
-
1986
- 1986-06-05 JP JP12922286A patent/JPH0739407B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62286984A (en) | 1987-12-12 |
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