(E)-1-phenyl-1-(phenylseleno)-2-(p-tolylsulfonyl)-1-propene | 86409-90-7

• 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)-1-phenyl-1-(phenylseleno)-2-(p-tolylsulfonyl)-1-propene
• 英文别名: (E)-phenyl(1-phenyl-2-tosylprop-1-en-1-yl)selane；1-methyl-4-[(E)-1-phenyl-1-phenylselanylprop-1-en-2-yl]sulfonylbenzene
• CAS: 86409-90-7
• 化学式: C₂₂H₂₀O₂SSe
• 分子量: 427.426
• InChiKey: KLRGADXBEUELOB-RELWKKBWSA-N

物化性质

• 熔点：
  99-100 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• 沸点：
  558.1±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-phenyl-1-(phenylseleno)-2-(p-tolylsulfonyl)-1-propene 在 间氯过氧苯甲酸 作用下， 反应 0.17h， 生成 1-methyl-4-[(E)-1-phenyl-1-phenylseleninylprop-1-en-2-yl]sulfonylbenzene
  参考文献：
  名称：

  Back, Thomas G.; Collins, Scott; Law, Kwok-Wai, Canadian Journal of Chemistry, 1985, vol. 63, p. 2313 - 2318

  摘要：

  DOI：
• 作为产物：
  描述：

  1-methyl-4-[(E)-1-phenyl-1-phenylseleninylprop-1-en-2-yl]sulfonylbenzene 、 偏二甲肼 以96%的产率得到
  参考文献：
  名称：

  BACK, TH. G.;COLLINS, S.;LAW, KWOK-WAI, CAN. J. CHEM., 1985, 63, N 8, 2313-2318

  摘要：

  DOI：

文献信息

• Copper-Catalyzed Three Component Regio- and Stereospecific Selenosulfonation of Alkynes: Synthesis of (<i>E</i>)-β-Selenovinyl Sulfones
  作者：Yang Liu、Guangfan Zheng、Qian Zhang、Yan Li、Qian Zhang

  DOI：10.1021/acs.joc.6b03049

  日期：2017.2.17

  A copper-catalyzed highly regio- and stereospecific selenosulfonation of alkynes with arylsulfonohydrazides and diphenyl diselenide has been developed. This novel three component reaction proceeds under very mild conditions and with a broad scope of substrates, providing a wide range of (E)-β-selenovinyl sulfones in good to excellent yields.

  已经开发了铜的炔烃与芳基磺酰肼和二苯基二硒化物的高度区域选择性和立体选择性硒代磺化反应。这种新颖的三组分反应在非常温和的条件下且在广泛的底物范围内进行，以良好至极佳的收率提供了多种（E）-β-硒代乙烯基砜。
• Selenosulfonation of disubstituted acetylenes: reactions of corresponding vinyl selenoxides and anomalous formation of a ketene diselenoacetal
  作者：Thomas G. Back、Scott Collins、Uday Gokhale、Kwok Wai Law

  DOI：10.1021/jo00172a066

  日期：1983.12
• Selenosulfonation of acetylenes: preparation of novel .beta.-(phenylseleno)vinyl sulfones and their conversion to acetylenic and .beta.-functionalized sulfones
  作者：Thomas G. Back、Scott Collins、Russell G. Kerr

  DOI：10.1021/jo00166a030

  日期：1983.9
• Synthesis of (<i>E</i>)-β-Selenovinyl Sulfones through a Multicomponent Regio- and Stereospecific Selenosulfonation of Alkynes with Insertion of Sulfur Dioxide
  作者：Kai Sun、Zuodong Shi、Zhenhua Liu、Baixue Luan、Jiali Zhu、Yanru Xue

  DOI：10.1021/acs.orglett.8b02733

  日期：2018.11.2

  A novel and practical method for the selenosulfonation of alkynes with the insertion of sulfur dioxide has been developed. A series of beta-(seleno)vinyl sulfones with high levels of regio- and stereoselectivity have been prepared. The key features of this reaction include a broad substrate scope, excellent functional-group tolerance, and amenability to scale-up synthesis. A plausible radical mechanism is proposed to illustrate this reaction.
• Substitution reactions of organocuprates with .beta.-(phenylseleno)vinyl sulfones derived from the selenosulfonation of acetylenes. A convenient and stereospecific preparation of vinyl sulfones and olefins from acetylenes
  作者：Thomas G. Back、Scott Collins、M. Vijaya Krishna、Kwok Wai Law

  DOI：10.1021/jo00228a019

  日期：1987.9