ethyl ester of β-(mercapto)cinnamic acid | 36367-20-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl ester of β-(mercapto)cinnamic acid
• 英文别名: β-Mercapto-zimtsaeure-ethylester；Ethyl-3-mercaptocinnamat；ethyl (Z)-3-phenyl-3-sulfanylprop-2-enoate
• CAS: 36367-20-1
• 化学式: C₁₁H₁₂O₂S
• 分子量: 208.281
• InChiKey: KITGQMUBFVFBRU-NTMALXAHSA-N

物化性质

• 沸点：
  326.1±42.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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 ester of β-(mercapto)cinnamic acid 生成 Ethyl 3-acetylthio-2-allyl-cinnamat
  参考文献：
  名称：

  烯硫醇的研究VII：某些烯硫醇衍生物的硫代claisen重排

  摘要：

  衍生自乙酰乙酸乙酯和苯甲酰基乙酸乙酯的乙硫醇已经用烯丙基-巴豆基和炔丙基溴烷基化，得到3-烷硫基巴豆酸乙酯（E-和Z-形式）和3-烷硫基肉桂酸乙酯（Z-形式）。烷基化的巴豆酸酯的Z-形式通过加热或辐射被平滑地转化为相应的E-形式。硫化物在乙酸酐，吡啶，三乙胺和喹啉等溶剂中进行不同的重排反应，从而产生了包括噻吩和2 H- thiopyran衍生物在内的各种产物。

  DOI：

  10.1016/0040-4020(72)88013-x
• 作为产物：
  描述：

  5-苯基-3H-1,2-二硫醇-3-酮 以50%的产率得到
  参考文献：
  名称：

  VASILEVA T. P.; BYSTROVA V. M.; LINKOVA M. G.; KILDISHEVA O. V.; KNUNYANT+, IZV. AN CCCP. CEP. XIM., 1981, HO 7, 1633-1636

  摘要：

  DOI：

文献信息

• The influence of substituents on preparation and tautomerism of open-chain β-thioketoesters
  作者：F. Duus

  DOI：10.1016/0040-4020(72)88125-0

  日期：1972.1

  the synthesis of β-thioketoesters, the acid catalysed reactions of 36 differently substituted β-keto esters with H2S have been studied under various conditions in order to determine the influence of the substituents on reaction course. gem-Dithiols may also be obtained in good yields by this reaction. Treatment of T1(I)-salts of β-thioketo esters with alkyl halides results exclusively in S-alkylation

  特别是关于β-硫代酮酸酯的合成，已经在各种条件下研究了36种不同取代的β-酮酸酯与H 2 S的酸催化反应，以确定取代基对反应过程的影响。通过该反应也可以高收率获得宝石-二硫醇。用烷基卤化物处理β-硫代酮酸酯的T1（I）-盐仅导致S-烷基化。证明了通过绕CC双键旋转，S-烷基化的α，β-不饱和β-巯基酯的缓慢的顺反异构体。硫代乙硫代乙酸乙酯是通过硫代乙酸乙酯的自缩合制备的。
• Reaction of 1,2-dithiolan- and 1,2-dithiolen-3-ones with phosphines
  作者：T. P. Vasil'eva、V. M. Bystrova、M. G. Lin'kova、O. V. Kil'disheva、I. L. Knunyants

  DOI：10.1007/bf01418003

  日期：1981.7
• Determination of tautomeric phenotypes of β-thioxo esters and characterization of the tautomeric enethiolic constituents by means of13C NMR spectroscopy
  作者：F. Duus、P. E. Hansen

  DOI：10.1002/mrc.1270220105

  日期：1984.1

  AbstractThe 13C NMR spectra of 28 enethiolizable β‐thioxo esters and 6 enethiolizable β‐thioxo thioloesters have been recorded in order to establish the tautomeric phenotypes of these compounds. All compounds investigated are essentially enethiolic. The carbonyl‐conjugated (Z)‐enethiol form is the exclusive or predominant tautomer of open‐chain β‐thioxo esters and thioloesters, thioacylmalonates and medium‐sized 2‐alkoxycarbonylcycloalkanethiones. The carbonyl‐conjugated (E)‐enethiol form is identifiable for open‐chain α‐unsubstituted β‐thioxo esters and thioloesters, and abundant for open‐chain α‐substituted β‐thioxo esters. Non‐conjugated enethiol forms [i.e. (Z)‐ and (E)‐isomeric β,γ‐unsaturated β‐mercapto esters] are abundant tautomeric constituents of ω‐substituted and higher 2‐alkoxycarbonylcycloalkanethiones. The chemical shifts of the carbon atoms directly involved in the tautomeric change have been rationalized in terms of substituent screening contributions. Deuterium isotope effects on the central carbon atoms of selected deuterio‐enethiolic compounds have been measured in order to depict the ester group rotamerism in CO‐conjugated (Z)‐enethiols. The abundance of the CO‐conjugated (E)‐enethiols, as well as the preferred population of the non‐conjugated (Z)‐enethiol form relative to the non‐conjugated (E)‐enethiol form, is rationalized in terms of the occurrence of a no‐bond interaction between the lone‐pair electrons of the enethiolic sulphur atom and the ‘chelating’ methylene hydrogen atoms of cis‐alkyl groups.
• Thiophene chemistry—XIX
  作者：B. Hedegaard、J.Z. Mortensen、S.-O. Lawesson

  DOI：10.1016/s0040-4020(01)98246-8

  日期：1971.1
• US4010141A
  申请人：——

  公开号：US4010141A

  公开（公告）日：1977-03-01