Z-3-phenyl-2-(phenylthio)propenoic acid | 58808-67-6

• 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: Z-3-phenyl-2-(phenylthio)propenoic acid
• 英文别名: Z-3-phenyl-2-(phenylthio)acrylic acid；(Z)-3-phenyl-2-phenylsulfanylprop-2-enoic acid
• CAS: 58808-67-6
• 化学式: C₁₅H₁₂O₂S
• 分子量: 256.325
• InChiKey: AYMHHNZJRYMOPW-KAMYIIQDSA-N

物化性质

• 熔点：
  139-139.5 °C
• 沸点：
  430.7±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Z-3-phenyl-2-(phenylthio)propenoic acid 在 草酰氯 、 双氧水 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 、 水 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 Z-3-phenyl-2-(phenylsulfonyl)propenoyl chloride
  参考文献：
  名称：

  用N-卤代琥珀酰亚胺卤化4-苯基-3-（苯基磺酰基）-2-氮杂环丁酮。动力学与热力学控制。

  摘要：

  DOI：

  10.1021/jo000273c
• 作为产物：
  描述：

  苯硫酚 生成 Z-3-phenyl-2-(phenylthio)propenoic acid
  参考文献：
  名称：

  RASTEJKENE, L. P.;VIDUGIRENE, V. I.;TALAJKITE, Z. A.;LUKOSHYAVICHYUTE, N.+, ZH. ORGAN. XIMII, 1984, 20, N 4, 713-717

  摘要：

  DOI：

文献信息

• Organylzinc Chalcogenolate Promoted Michael-Type Addition of α,β-Unsaturated Carbonyl Compounds
  作者：Vanessa Lóren Nunes、Ingryd Cristina de Oliveira、Olga Soares do Rêgo Barros

  DOI：10.1002/ejoc.201301497

  日期：2014.3

  chalcogenide compounds promoted by organylzinc chalcogenolates. In this protocol, reductive cleavage of diorganyl dichalcogenide bonds by the Zn/NH4OH system led to organylzinc chalcogenolates. The reaction was performed with propiolic acids and esters and afforded β-organochalcogenacrylic acids and esters under mild basic conditions. The stereochemistry corresponded to anti-Markovnikov addition of the organyl

  我们介绍了有机基锌硫属元素化物促进的乙烯基硫属元素化物化合物的化学、区域和立体选择性合成。在该协议中，Zn/NH4OH 系统对二有机二硫属化物键的还原裂解导致有机锌硫属元素酸盐。该反应用丙炔酸和酯进行，在温和的碱性条件下得到 β-有机硫代丙烯酸和酯。立体化学对应于跨三键的有机硫族化合物成分的反马尔科夫尼科夫加成。
• Activated Michael Acceptors as Precursors to Heterocycles. 1. 2-Azetidinones from 2-(Arylsulfonyl)propenoyl Chlorides and Amines
  作者：Feng Zhou、Jonathan Rosen、Jennifer M. Zebrowski-Young、Patricia M. Freihammer、Michael R. Detty、Rene J. Lachicotte

  DOI：10.1021/jo980234p

  日期：1998.8.1

  The addition of NH3 and other primary amines to Z-3-phenyl-2-(arylsulfonyl)propenoyl chlorides gives trans-2-arylsulfonyl-3-phenyl-2-azetidinones as the major product in addition to the corresponding 2-arylsulfonyl-3-phenylpropenamide. Electron-withdrawing substituents in the arylsulfonyl group increased the percentage of products derived from 1,4-addition relative to 1,2-addition, while electron-donating substituents increased the amount of 1,2-addition observed in the product mixture. Addition of alpha-methylbenzylamine gave a 68:32 mixture of the two diastereomers of the trans-azetidinone. The major diastereomer was identified as the 1-(1R)-(3S,4S) and 1-(1S)-(3R,4R) enantiomers 16a by single-crystal X-ray crystallographic analysis, Phenylthio and phenylsulfoxo substituents did not promote 1,4-addition, although the addition of ammonia to Z-3-phenyl-2-(phenylsulfoxo)propenoyl chloride (7a) gave a 95:5 ratio of the corresponding propenamide 8a and a 3-(phenylsulfoxo)azetidinone 9a. trans-4-Phenyl-3-(arylsulfonyl)-2-azetidinones 12a and 12c were sulfonated by the pyridine-SO3 complex to give the corresponding N-sulfonates 28 in > 80% yield. The p-methoxybenzyl substituent of 15 was removed by eerie ammonium nitrate in CH3CN to give 12a in 70% yield.
• Rasteikene, L. P.; Vidugirene, V. I.; Talaikite, Z. A., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 647 - 651
  作者：Rasteikene, L. P.、Vidugirene, V. I.、Talaikite, Z. A.、Lukoshyavichyute, N. M.

  DOI：——

  日期：——
• WADSWORTH D. H.; DETTY M. R., J. ORG. CHEM., 1980, 45, NO 23, 4611-4615
  作者：WADSWORTH D. H.、 DETTY M. R.

  DOI：——

  日期：——
• Halogenation of 4-Phenyl-3-(phenylsulfonyl)-2-azetidinones with <i>N</i>-Halosuccinimides. Kinetic vs Thermodynamic Control
  作者：Patricia M. Freihammer、Michael R. Detty

  DOI：10.1021/jo000273c

  日期：2000.10.1