(rac)-2-(tert-butylsulfinyl)phenyl-(E)-2,4-diphenylbut-3-enyl selenide | 1242149-04-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (rac)-2-(tert-butylsulfinyl)phenyl-(E)-2,4-diphenylbut-3-enyl selenide
• 英文别名: 2-(tert-butylsulfinyl)phenyl (E)-2,4-diphenylbut-3-enyl selenide；1-tert-butylsulfinyl-2-[(E)-2,4-diphenylbut-3-enyl]selanylbenzene
• CAS: 1242149-04-7
• 化学式: C₂₆H₂₈OSSe
• 分子量: 467.534
• InChiKey: QQFCMYRHBDNSND-VHEBQXMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙烯 、 bis[2-(tert-butylsulfinyl)phenyl]diselenide 在 溴 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 0.75h， 以30%的产率得到(rac)-2-(tert-butylsulfinyl)phenyl-(E)-2,4-diphenylbut-3-enyl selenide
  参考文献：
  名称：

  Selenenylations of alkenes with styrene nucleophiles

  摘要：

  Iodine-mediated addition reactions to alkenes with diphenyl diselenide using the same alkenes as nucleophiles are presented. The transformation proceeds under mild reaction conditions and the addition products were isolated in moderate to good yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.034

文献信息

• Synthesis of New Sulfoxide-Containing Diselenides and Unexpected Cyclization Reactions to 2,3-Dihydro-1,4-benzoselenothiine 1-Oxides
  作者：Diana M. Freudendahl、Michio Iwaoka、Thomas Wirth

  DOI：10.1002/ejoc.201000514

  日期：——

  functionalization of alkenes. The influence of solvents and different nucleophiles on the outcome of the selenenylation reaction was studied. Besides the successful selenenylation reactions, one selenium electrophile showed an unexpected reactivity in forming a six-membered heterocyclic system upon reaction with alkenes. A mechanism for the formation of these 2,3-dihydro-1,4-benzoselenothiine 1-oxides is proposed

  制备了新型手性含亚砜的二硒化物，并将其相应的硒亲电试剂用于烯烃的立体选择性功能化。研究了溶剂和不同亲核试剂对硒基化反应结果的影响。除了成功的硒基化反应外，一种硒亲电试剂在与烯烃反应后形成六元杂环系统时表现出意想不到的反应性。提出了这些 2,3-二氢-1,4-苯硒代硒 1-氧化物的形成机制。
• Selenenylations of alkenes with styrene nucleophiles
  作者：Elena Gabriele、Fateh V. Singh、Diana M. Freudendahl、Thomas Wirth

  DOI：10.1016/j.tet.2012.08.034

  日期：2012.12

  Iodine-mediated addition reactions to alkenes with diphenyl diselenide using the same alkenes as nucleophiles are presented. The transformation proceeds under mild reaction conditions and the addition products were isolated in moderate to good yields. (C) 2012 Elsevier Ltd. All rights reserved.