(E)-2-Thienyl β-styryl sulfide | 113791-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-Thienyl β-styryl sulfide
• 英文别名: trans-1-phenyl-2-(2-thienylthio)ethene；(E)-2-(styrylthio)thiophene；2-[(E)-2-phenylethenyl]sulfanylthiophene
• CAS: 113791-96-1
• 化学式: C₁₂H₁₀S₂
• 分子量: 218.343
• InChiKey: AUBLGYYVCQSCDN-CSKARUKUSA-N

物化性质

• 沸点：
  132-140 °C(Press: 1 Torr)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-dibromostyrene 在 Ni(xantphos)(o-tolyl)Cl 、 potassium acetate 、 三乙胺 、 亚磷酸二甲酯 、 sodium hydroxide 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 13.5h， 生成 (E)-2-Thienyl β-styryl sulfide
  参考文献：
  名称：

  镍催化实现的烯基硫醚化

  摘要：

  本文描述了一种有效的策略，通过镍催化的失活或 β-芳基取代的 ( E )-烯基卤化物与硫醇/酚的交叉偶联来促进烯基硫醚化。本策略具有易于操作的反应条件，代表了通过易于获得的镍催化形成最有效的烯基 C(sp 2 )–S 键的方法之一。值得注意的是，所采用的温和碱性条件有助于获得广泛的范围，包括受保护的氨基酸、糖类和杂环化合物。此外，这项工作通过在几种结构复杂的天然产物和药物的后期修饰中的应用展现了其极具吸引力的实用性。

  DOI：

  10.1021/acs.joc.3c00049

文献信息

• Kuznetsova, M. A.; Korchevin, N. A.; Deryagina, E. N., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 6, p. 1136 - 1140
  作者：Kuznetsova, M. A.、Korchevin, N. A.、Deryagina, E. N.、Voronkov, M. G.

  DOI：——

  日期：——
• Free-Radical Addition of Heteroarenethiols and Heteroarylmethanethiols to Hexyne and Phenylacetylene. Chemical Behavior of the Transient .beta.-Sulfanylvinyl Radicals
  作者：Luisa Benati、Laura Capella、Pier Carlo Montevecchi、Piero Spagnolo

  DOI：10.1021/jo00129a039

  日期：1995.12

  The free-radical reaction of a number of heteroarenethiols (including 2-thiophene-, 2-benzo[b]furan-and 2-benzo[b]thiophenethiol) and heteroarylmethanethiols (including 2-furyl-, 2-thienyl-, and 3-thienylmethanethiol) with hex-1-yne and phenylacetylene has been investigated in benzene solution both at 100 degrees C in the presence of AIBN and at room temperature in the presence of BEt(3)/O-2. Under both of these conditions the above thiols generally furnished transient 2-sulfanylvinyl radicals through regioselective addition of corresponding sulfanyl radicals to the terminal alkyne carbon, but 2-benzo[b]furanthiol failed to react with either alkyne in the presence of BEt(3)/O-2 and unexpectedely gave 2-(ethylsulfanyl)benzo[b]furan to a significant extent. The produced 2-(2-heteroarylsulfanyl) vinyl radicals largely preferred to undergo intermolecular H-abstraction reaction rather than intramolecular 5-endo cyclization onto the heteroaryl moiety of the 2-sulfanyl substituent. The 2-[(2-thienylmethyl)sulfanyl]- and, especially, 2-[(2-furylmethyl)sulfanyl]vinyl radicals, besides H-abstraction, promptly underwent intramolecular B-exo cyclization to give spiro radicals that interestingly underwent beta-scission of their respective C-S and C-O bond resulting in ring cleavage of the original heteroaryl group. The 2-[(3-thienylmethyl)sulfanyl]vinyl radicals did not exhibit any similar B-exo cyclization, but did undergo a 6-endo cyclization to a very slight extent.
• Reaction of the System Arene(Hetarene)thiol-Diselenide with Phenylacetylene
  作者：L. K. Papernaya、A. I. Albanov、E. N. Sukhomazova、E. P. Levanova、E. N. Deryagina

  DOI：10.1023/b:rugc.0000039083.59169.f3

  日期：2004.5

  Liquid-phase thermal reactions of phenylacetylene with the system arene(hetarene)thiol-diselertide at 110-180degreesC proceed through conjugate addition to the phenylacetylene triple bond of one alkylselanyl and one arene(hetarenesulfanyl groups to form 2-alkylselanyl-2-[aryl(hetaryl)sulfanyl]-1-phenylethenes and 1-alkylselanyl-2-[aryl(hetaryl)sulfanyl]-1-phenylethenes. Therewith, direct addition of thiols to phenylacetylene slows down.
• KUZNETSOVA M. A.; KORCHEVIN N. A.; DERYAGINA EH. N.; VORONKOV M. G., ZH. ORGAN. XIMII, 23,(1987) N 6, 1255-1260
  作者：KUZNETSOVA M. A.、 KORCHEVIN N. A.、 DERYAGINA EH. N.、 VORONKOV M. G.

  DOI：——

  日期：——
• Alkenyl Thioetherification Enabled by Nickel Catalysis
  作者：Bing Xu、Huan Xiang、Yuqiong Tan、Ze Li、Shijun Li、Xiang-Yang Ye、Yang Ye

  DOI：10.1021/acs.joc.3c00049

  日期：——

  This paper describes an efficient strategy to promote alkenyl thioetherifications via the Ni-catalyzed cross-coupling of inactivated or β-aryl-substituted (E)-alkenyl halides with thio-alcohols/phenols. The present strategy with easy-to-operate reaction conditions represents one of the most effective alkenyl C(sp2)–S bond-forming methods via readily accessible nickel catalysis. Notably, the mildly

  本文描述了一种有效的策略，通过镍催化的失活或 β-芳基取代的 ( E )-烯基卤化物与硫醇/酚的交叉偶联来促进烯基硫醚化。本策略具有易于操作的反应条件，代表了通过易于获得的镍催化形成最有效的烯基 C(sp 2 )–S 键的方法之一。值得注意的是，所采用的温和碱性条件有助于获得广泛的范围，包括受保护的氨基酸、糖类和杂环化合物。此外，这项工作通过在几种结构复杂的天然产物和药物的后期修饰中的应用展现了其极具吸引力的实用性。