KR970061862A - (±) -2- (tolylsulfinyl) -cyclopentadecan-1-one and its preparation method - Google Patents

(±) -2- (tolylsulfinyl) -cyclopentadecan-1-one and its preparation method Download PDF

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KR970061862A
KR970061862A KR1019960004716A KR19960004716A KR970061862A KR 970061862 A KR970061862 A KR 970061862A KR 1019960004716 A KR1019960004716 A KR 1019960004716A KR 19960004716 A KR19960004716 A KR 19960004716A KR 970061862 A KR970061862 A KR 970061862A
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solvent
formula
alcohol
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mixed solvent
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KR0179320B1 (en
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박대규
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박대규
조선무약 합자회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C325/00—Thioaldehydes; Thioketones; Thioquinones; Oxides thereof

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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

본 발명은 신규 화합물인 하기 구조식(Ⅰ)의 (+)-2-(톨릴술피닐)-시클로펜타데칸-1-온 및 그의 제조방법, 합성중간체로의 용도에 관한 것으로,The present invention relates to ( + ) - 2- (tolylsulfinyl) -cyclopentadecan-1-one of the following formula (I) which is a novel compound, its preparation method and its use as a synthetic intermediate,

구조식(Ⅰ)의 신규 화합물은 중추신경계에 작용하는 하기 구조식(Ⅱ)의 디엘-3-메칠-시클로펜타데칸-1-온의 제조시 합성중간체로 매우 유용하다.The novel compounds of formula (I) are very useful as synthetic intermediates in the preparation of di-3-methyl-cyclopentadecan-1-one of the following formula (II) which acts on the central nervous system.

Description

(+)-2-(톨릴술피닐)-시클로펜타데칸-1-온 및 그의 제법(+) - 2- (tolylsulfinyl) -cyclopentadecan-1-one and its preparation method

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

Claims (8)

티오닐클로라이드와 파라-톨루엔술핀산나트륨염을 반응시켜 오일상의 파라-톨루엔술피닐클로라이드를 얻고 이를 유기혼합용매 존재하 아실화반응시켜 구조식(Ⅳ)로 표시되는 유황화합물을 얻은 후, 구조식(Ⅲ)으로 표시되는 시클로펜타데칸-1-온을 비극성 유기용매에 용해시킨 후 유황화합물(Ⅳ)과 엔올화제를 첨가하여 술피닐화 반응시켜 구조식(Ⅰ)로 표시되는 (±)-2-(톨릴술피닐)-시클로펜타데칸-1-온을 제조함을 특징으로 하는 방법.Toluenesulfinyl chloride was obtained by reacting thionyl chloride with para-toluenesulfinic acid sodium salt, and this was subjected to an acylation reaction in the presence of an organic mixed solvent to obtain a sulfur compound represented by the formula (IV) Cyclopentadecan-1-one represented by the structural formula (I) is dissolved in a nonpolar organic solvent, and then a sulfur compound (IV) and an enolizing agent are added to effect a sulfinylation reaction to obtain (±) -2- Trifluoromethyl-phenyl) -cyclopentadecan-l-one. ≪ / RTI > 상기 식에서, X는 SOTol, R은 엘-멘칠 또는 알킬기를 나타내며, Tol은 톨릴기를 의미하고 알킬기는 메칠, 에틸, 푸로필 또는 이소푸로필기를 의미한다.Wherein X represents SOTol, R represents an el-menthyl or an alkyl group, Tol represents a tolyl group, and the alkyl group means a methyl, ethyl, furoyl, or isophoryl group. 제1항에 있어서, 구조식(Ⅳ)의 화합물의 제조시 반응온도는 0 내지 10℃의 온도범위에서 2-3시간을 실행함을 특징으로 하는 방법.The process according to claim 1, wherein the reaction temperature in the preparation of the compound of formula (IV) is in the range of 0 to 10 C for 2 to 3 hours. 제1항에 있어서, 구조식(Ⅳ) 화합물의 제조에 사용되는 유기혼합 용매는 비극성용매와 극성용매의 혼합용매로서, 비극성용매로는 에칠에테르, 메칠에칠에테르 또는 이소푸로필에칠에테르중에서 선택되며, 극성용매로는 에칠알코올, 메틸알코올, 프로필알코올, 부틸알코올, 이소부틸알코올 또는 피리딘중에서 선택사용됨을 특징으로 하는 방법.The organic solvent mixture according to claim 1, wherein the organic mixed solvent used for preparing the structural formula (IV) is a mixed solvent of a nonpolar solvent and a polar solvent, and the nonpolar solvent is selected from ethyl ether, methyl ethyl ether or isopropyl alcohol ethyl ether And the polar solvent is selected from among ethyl alcohol, methyl alcohol, propyl alcohol, butyl alcohol, isobutyl alcohol or pyridine. 제3항에 있어서, 유기 혼합용매는 무수에칠에테르와 피리딘의 2 : 1~3 : 1혼합용매임을 특징으로 하는 방법.4. The method according to claim 3, wherein the organic mixed solvent is a mixed solvent of anhydrous ethyl ether and pyridine in a ratio of 2: 1 to 3: 1. 제1항에 있어서, 엔올화제로는 H2의 염(수산화나트륨, 수산화칼슘, 수산화리튬) 또는 아미드화염(나트륨, 리튬)을 사용하며, 그중 아미드화나트륨이 가장 바람직하며, 그 양은 구조식(Ⅲ) 화합물에 대하여 0.1 내지 5.0몰비를, 바람직하게는 0.5~2.0몰비를 사용함을 특징으로 하는 제조방법.[2] The method according to claim 1, wherein the enolizing agent is a salt of H 2 (sodium hydroxide, calcium hydroxide, lithium hydroxide) or an amide flame (sodium or lithium), most preferably sodium amidate, To the compound is used in a molar ratio of 0.1 to 5.0, preferably 0.5 to 2.0. 제1항에 있어서, 엔올화반응은 30-50℃에서 1 내지 2시간동안 반응시킴을 특징으로 하는 방법.The process according to claim 1, wherein the enolization reaction is carried out at 30-50 ° C for 1 to 2 hours. 하기 구조식(Ⅰ)의 신규화합물.A novel compound of structure (I) 상기 식에서, X는 SOTol 이고, Tol은 톨릴기를 의미한다.Wherein X is SOTol and Tol is a tolyl group. 하기 구조식(Ⅰ)의 화합물을 구조식(Ⅱ) 화합물의 합성중간체로 사용하는 용도.Use of a compound of formula (I) below as a synthetic intermediate of formula (II). 상기 식에서, X는 SOTol 이고, Tol은 톨릴기를 의미한다.Wherein X is SOTol and Tol is a tolyl group. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019960004716A 1996-02-27 1996-02-27 (+-)-2-(tolylsulfinyl)-cyclopentadecan-1-one and process for preparation thereof KR0179320B1 (en)

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KR1019960004716A KR0179320B1 (en) 1996-02-27 1996-02-27 (+-)-2-(tolylsulfinyl)-cyclopentadecan-1-one and process for preparation thereof

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KR0179320B1 KR0179320B1 (en) 1999-05-15

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