ethyl 3-sulfanylhexanoate | 309250-83-7

• 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-sulfanylhexanoate
• CAS: 309250-83-7
• 化学式: C₈H₁₆O₂S
• 分子量: 176.28
• InChiKey: HTFAPDVTXLGQAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  27.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-sulfanylhexanoate 在 lithium aluminium deuteride 、 溶剂黄146 、 锌 作用下， 以 乙醚 为溶剂， 反应 7.0h， 生成 [2H2]-3-sulfanylhexan-1-ol
  参考文献：
  名称：

  Quantitative Determination of Sulfur Containing Wine Odorants at Sub-ppb Levels. 1. Synthesis of the Deuterated Analogues

  摘要：

  [H-2(10)]-4-Sulfanyl-4-methylpentan-2-one (d(10)-SMP), [H-2(2)]-3-sulfanylhexan-1-ol (d(2)-3SH), and [H-2(5)]-3-sulfanylhexyl acetate (d(5)-3SHAc), the -labeled analogues of impact odorants of wines and other foods, were synthesized to be used for the quantitative determination of the natural compounds in white and red wines by stable isotope dilution assay. The sulfidation was achieved by Michael addition, on mesityl oxide or ethyl hex-2-enoate, respectively, of the sulfhydryl anion generated in situ from triphenylsilanethiol and potassium fluoride under phase transfer conditions. The labeling of 4-sulfanyl-4-methylpentan-2-one (SMP) was obtained from the commercial starting material, [H-2(6)]-acetone, so that this method could be used to synthesize C-13-labeled SMP from 13C-labeled acetone. The labeling of 3-sulfanylhexan-1-ol (3SH) and 3-sulfanylhexyl acetate (3SHAc) was obtained from reduction with lithium aluminum deuteride of the Michael adduct ethyl 5-sulfanylhexanoate and [H-2(3)]-acetylation. During the synthesis, 3SH and 3SHAc were partially oxidized to their disulfide, which were reduced back to the thiols by an additional reduction step; the tertiary thiol SMP was less sensitive to this oxidation..

  DOI：

  10.1021/jf0004715
• 作为产物：
  描述：

  反式-2-己烯酸乙酯 在 potassium fluoride 、 18-冠醚-6 、 溶剂黄146 、 锌 、 三苯基硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 ethyl 3-sulfanylhexanoate
  参考文献：
  名称：

  Quantitative Determination of Sulfur Containing Wine Odorants at Sub-ppb Levels. 1. Synthesis of the Deuterated Analogues

  摘要：

  [H-2(10)]-4-Sulfanyl-4-methylpentan-2-one (d(10)-SMP), [H-2(2)]-3-sulfanylhexan-1-ol (d(2)-3SH), and [H-2(5)]-3-sulfanylhexyl acetate (d(5)-3SHAc), the -labeled analogues of impact odorants of wines and other foods, were synthesized to be used for the quantitative determination of the natural compounds in white and red wines by stable isotope dilution assay. The sulfidation was achieved by Michael addition, on mesityl oxide or ethyl hex-2-enoate, respectively, of the sulfhydryl anion generated in situ from triphenylsilanethiol and potassium fluoride under phase transfer conditions. The labeling of 4-sulfanyl-4-methylpentan-2-one (SMP) was obtained from the commercial starting material, [H-2(6)]-acetone, so that this method could be used to synthesize C-13-labeled SMP from 13C-labeled acetone. The labeling of 3-sulfanylhexan-1-ol (3SH) and 3-sulfanylhexyl acetate (3SHAc) was obtained from reduction with lithium aluminum deuteride of the Michael adduct ethyl 5-sulfanylhexanoate and [H-2(3)]-acetylation. During the synthesis, 3SH and 3SHAc were partially oxidized to their disulfide, which were reduced back to the thiols by an additional reduction step; the tertiary thiol SMP was less sensitive to this oxidation..

  DOI：

  10.1021/jf0004715

文献信息

• 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）。
• US3954843A
  申请人：——

  公开号：US3954843A

  公开（公告）日：1976-05-04
• US8536364B2
  申请人：——

  公开号：US8536364B2

  公开（公告）日：2013-09-17
• Quantitative Determination of Sulfur Containing Wine Odorants at Sub-ppb Levels. 1. Synthesis of the Deuterated Analogues
  作者：Yorgos Kotseridis、Jean-Loïc Ray、Christian Augier、Raymond Baumes

  DOI：10.1021/jf0004715

  日期：2000.12.1

  [H-2(10)]-4-Sulfanyl-4-methylpentan-2-one (d(10)-SMP), [H-2(2)]-3-sulfanylhexan-1-ol (d(2)-3SH), and [H-2(5)]-3-sulfanylhexyl acetate (d(5)-3SHAc), the -labeled analogues of impact odorants of wines and other foods, were synthesized to be used for the quantitative determination of the natural compounds in white and red wines by stable isotope dilution assay. The sulfidation was achieved by Michael addition, on mesityl oxide or ethyl hex-2-enoate, respectively, of the sulfhydryl anion generated in situ from triphenylsilanethiol and potassium fluoride under phase transfer conditions. The labeling of 4-sulfanyl-4-methylpentan-2-one (SMP) was obtained from the commercial starting material, [H-2(6)]-acetone, so that this method could be used to synthesize C-13-labeled SMP from 13C-labeled acetone. The labeling of 3-sulfanylhexan-1-ol (3SH) and 3-sulfanylhexyl acetate (3SHAc) was obtained from reduction with lithium aluminum deuteride of the Michael adduct ethyl 5-sulfanylhexanoate and [H-2(3)]-acetylation. During the synthesis, 3SH and 3SHAc were partially oxidized to their disulfide, which were reduced back to the thiols by an additional reduction step; the tertiary thiol SMP was less sensitive to this oxidation..