ethyl 3-(acetylthio)butanoate | 92065-74-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-(acetylthio)butanoate
• 英文别名: ethyl 3-acetylthiobutanoate；β-(Acetylthio)-buttersaeure-ethylester；Ethyl 3-acetylsulfanylbutanoate
• CAS: 92065-74-2
• 化学式: C₈H₁₄O₃S
• 分子量: 190.263
• InChiKey: NLPXIBXNVOMOFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  53 °C(Press: 0.05 Torr)
• 密度：
  1.083±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(acetylthio)butanoate 在 磷脂酶B 作用下， 反应 3.0h， 生成 3-mercaptobutyric acid 、 3-(乙酰基硫烷基)丁酸
  参考文献：
  名称：

  Flavouring and odorant thiols from renewable natural resources by InIII-catalysed hydrothioacetylation and lipase-catalysed solvolysis

  摘要：

  A chemoenzymatic access to thiol compounds, including ethyl 3-thiobutanoate, 3-thio-p-menthene and 8-thio-p-menthan-2-one, three compounds of interest in flavour and fragrance chemistry presenting various fruity notes, is proposed. It involves an indium(III)-catalysed hydrothioacetylation of renewable precursors followed by an enzymatic solvolysis of the obtained thioesters by lipases in aqueous or organic solvents. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.081
• 作为产物：
  描述：

  反式-2-丁烯酸乙酯 、 硫代乙酸 在 indium(III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 以99%的产率得到ethyl 3-(acetylthio)butanoate
  参考文献：
  名称：

  Flavouring and odorant thiols from renewable natural resources by InIII-catalysed hydrothioacetylation and lipase-catalysed solvolysis

  摘要：

  A chemoenzymatic access to thiol compounds, including ethyl 3-thiobutanoate, 3-thio-p-menthene and 8-thio-p-menthan-2-one, three compounds of interest in flavour and fragrance chemistry presenting various fruity notes, is proposed. It involves an indium(III)-catalysed hydrothioacetylation of renewable precursors followed by an enzymatic solvolysis of the obtained thioesters by lipases in aqueous or organic solvents. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.081

文献信息

• Stereoselective reduction of thiocarbonyl compounds with baker's yeast
  作者：Jens Kaergaard Nielsen、Jergen Øgaard Madsen

  DOI：10.1016/s0957-4166(00)86212-6

  日期：1994.3

  2-octanethione have been reduced with baker's yeast to give optically active thiols. The reductions parallel those of the oxygen analogues with respect to rate and diastereo- and enantioselectivity but, generally, the enantiomeric excess (ee) values are smaller. The influence of experimental variables such as substrate concentration, physiological condition of the yeast (resting/fermenting, fresh/dry/frozen)

  用面包酵母还原3-硫代-丁酸，-戊酸和-己酸的烷基酯，2-硫代-1-环戊烷氧羰酸乙酯和2-辛烷硫酮，以得到光学活性的硫醇。在速率和非对映选择性和对映选择性方面，该减少量与氧类似物的减少量平行，但通常，对映体过量（ee）值较小。研究了诸如底物浓度，酵母的生理条件（静止/发酵，新鲜/干燥/冷冻），底物修饰以及抑制剂的添加等对立体选择性的影响。底物浓度低，使用干酵母或冷冻酵母以及添加R酶抑制剂（丙烯酸乙酯和联乙酰）有利于S产物的形成。硫醇产物的产率受到所用所有底物的巯基广泛水解的限制。为了对不同底物的面包酵母还原中的对映体偏好进行有意义的填充比较，建议使用最大ee值低于某些（取决于底物的）底物/酵母比率的最大ee值。
• METHOD FOR PRODUCING SULFUR-CONTAINING CARBOXYLIC ACID ESTERS
  申请人：Inaba Teruhiko

  公开号：US20110282089A1

  公开（公告）日：2011-11-17

  The present invention provides a method for producing sulfur-containing carboxylic acid esters that are useful for aromatizing and flavoring purpose and can cater to the needs for diversified aromatized and/or flavored products, and to further provide a fragrance and/or flavor composition comprising the ester producible by the method and an aromatized and/or flavored product comprising the same. The sulfur-containing carboxylic acid ester is represented by the following formula (3): wherein R 1 represents an alkyl group having 1 to 10 carbon atoms or an optionally substituted phenyl group (wherein the substituent thereof is an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms), R 2 and R 3 independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, or R 2 and R 3 together form an alkylene group, and R 4 represents an alkyl group having 1 to 4 carbon atoms.

  本发明提供了一种用于生产含硫羧酸酯的方法，这些酯对于芳香和调味目的非常有用，并且可以满足多样化芳香和/或调味产品的需求，进一步提供了一种香味和/或味道组合物，该组合物由通过该方法可制备的酯和包含该酯的芳香和/或调味产品组成。含硫羧酸酯由以下式子（3）表示：其中，R1表示具有1至10个碳原子的烷基或可选择取代的苯基（其取代基为具有1至4个碳原子的烷基或1至4个碳原子的烷氧基），R2和R3独立地表示氢原子、具有1至10个碳原子的烷基或具有2至10个碳原子的烯基，或R2和R3一起形成烷基。R4表示具有1至4个碳原子的烷基。
• Method for producing sulfur-containing carboxylic acid esters
  申请人：Takasago International Corporation

  公开号：EP2452933A1

  公开（公告）日：2012-05-16

  An object of the present invention is to provide a method for producing sulfur-containing carboxylic acid esters that are useful for aromatizing and flavoring purpose and can cater to the needs for diversified aromatized and/or flavored products, and to further provide a fragrance and/or flavor composition comprising the ester producible by the method and an aromatized and/or flavored product comprising the same. The present invention provides a method for producing a sulfur-containing carboxylic acid ester represented by the following formula (3): (wherein R1 represents an alkyl group having 1 to 10 carbon atoms or an optionally substituted phenyl group (wherein the substituent thereof is an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms), R2 and R3 independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, or R2 and R3 together form an alkylene group, and R4 represents an alkyl group having 1 to 4 carbon atoms), the method comprising a reaction of, in the presence of an acid catalyst, an α,β-unsaturated carboxylic acid ester represented by the following general formula (1): (wherein R1, R2 and R3 have the same meanings as defined above, and the wavy line represents cis or trans configuration), with a thiocarboxylic acid represented by the following general formula (2): (wherein R4 has the same meaning as defined above).

  本发明的目的是提供一种生产含硫羧酸酯的方法，该羧酸酯可用于芳香化和调味目的，并可满足多样化芳香化和/或调味产品的需求，并进一步提供一种包含通过该方法生产的酯的香料和/或调味组合物，以及包含该酯的芳香化和/或调味产品。 本发明提供了一种生产下式（3）所代表的含硫羧酸酯的方法： (其中 R1 代表具有 1 至 10 个碳原子的烷基或任选取代的苯基（其中其取代基为具有 1 至 4 个碳原子的烷基或具有 1 至 4 个碳原子的烷氧基），R2 和 R3 独立地代表氢原子、R2和R3分别代表氢原子、具有1至10个碳原子的烷基或具有2至10个碳原子的烯基，或R2和R3共同形成亚烷基，R4代表具有1至4个碳原子的烷基），该方法包括在酸催化剂存在下，与下通式(1)代表的α，β-不饱和羧酸酯反应： (其中 R1、R2 和 R3 的含义与上述定义相同，波浪线代表顺式或反式构型）与下 列通式 (2) 所代表的硫代羧酸进行反应： (其中 R4 的含义与上述定义相同）。
• Catalyst components for the polymerization of olefins
  申请人：BASELL POLIOLEFINE ITALIA S.R.L.

  公开号：US10011668B2

  公开（公告）日：2018-07-03

  The present disclosure relates to a catalyst component for the polymerization of olefins comprising Mg. Ti and an electron donor such as mercaptoester derivatives of the general formula (I). in which Z is selected from C, Si, O, N, S or P, with the proviso that the atoms O, S, P and N are not directly linked to either the carboxylic group or the sulfur atom of formula (I), the R2 groups, equal to or different from each other, are selected from hydrogen or a C1-C20 hydrocarbon radicals, optionally containing a heteroatom selected from halogen, P, S, N, O and Si, which can be fused together to form one or more cycles, m is a number satisfying the valences of Z and n is an integer ranging from 1 to 10, X is O or S, Y is —OR3, —NR4R5) or R6 groups in which R1 and R3 are selected from C1-C15 hydrocarbon groups, optionally containing a heteroatom selected from halogen, P, S, N, O, and Si, R4-R5 groups, independently, are hydrogen or R1 groups, and R6 groups have the same composition as R1 groups.

  本公开涉及一种用于烯烃聚合的催化剂组分，由 Mg.Ti和电子供体，如通式(I)的巯基酯衍生物。 其中 Z 选自 C、Si、O、N、S 或 P，但 O、S、P 和 N 原子不与式 (I) 的羧基或硫原子直接相连，R2 基团彼此相等或不同，选自氢或 C1-C20 烃基，任选含有选自卤素、P、S、N、O 和 Si 的杂原子，可融合在一起形成一个或多个循环、m是满足Z的价数，n是1至10的整数，X是O或S，Y是-OR3、-NR4R5）或R6基团，其中R1和R3选自C1-C15烃基，任选含有选自卤素、P、S、N、O和Si的杂原子，R4-R5基团独立地为氢或R1基团，R6基团的组成与R1基团相同。
• 531. Antituberculous sulphur compounds. Part I. New mercapto-derivatives of alkanols, sulphides, and hydroxy-sulphides
  作者：E. P. Adams、F. P. Doyle、D. L. Hatt、D. O. Holland、W. H. Hunter、K. R. L. Mansford、J. H. C. Nayler、A. Queen

  DOI：10.1039/jr9600002649

  日期：——