(2-(N-carbazolyl)-2-(phenylseleno)ethyl)methylpropanedinitrile | 141439-35-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2-(N-carbazolyl)-2-(phenylseleno)ethyl)methylpropanedinitrile
• 英文别名: 2-(2-carbazol-9-yl-2-phenylselanylethyl)-2-methylpropanedinitrile
• CAS: 141439-35-2
• 化学式: C₂₄H₁₉N₃Se
• 分子量: 428.395
• InChiKey: DRYSODAIIDPWMK-UHFFFAOYSA-N

物化性质

• 沸点：
  572.9±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.51
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  苯基溴化硒 在 偶氮二异丁腈 、 sodium hydride 作用下， 以 氯仿 为溶剂， 反应 33.0h， 生成 (2-(N-carbazolyl)-2-(phenylseleno)ethyl)methylpropanedinitrile
  参考文献：
  名称：

  Group Transfer Addition Reactions of Methyl (phenylseleno)malononitrile to Alkenes

  摘要：

  Results of a detailed study of group transfer additions of methyl(phenylseleno)propanedinitrile (4) to a wide variety of alkenes are reported. For example, heating of 4 (60 degrees C) with 1-hexene and AIBN produces (2-(phenylseleno)-hexyl)methylpropanedinitrile in 97% yield. Reagent 4 adds in high yields to monosubstituted styrenes, enol ethers, enol acetates, enol sulfides, enamides, and enol imidazoles and carbazoles. Additions to many classes of 1,2-disubstituted alkenes also occur, and modest to good levels of 1,2-asymmetric induction are observed in the selenium transfer step. Oxygen- and sulfur-substituted alkenes produce anti products, and N-substituted alkenes produce syn products. The proposed mechanism involves radical addition followed by phenylselenium group transfer, and it is shown that radical additions to certain classes of disubstituted alkenes can be reversible. Additions to trisubstituted alkenes fair, probably because of this reversibility. Competition studies provide a relative reactivity scale of alkenes toward the electrophilic methylpropanedinitrile radical. Finally, a series of transformations serve to illustrate some synthetic possibilities for the products of these selenium transfer addition reactions.

  DOI：

  10.1021/ja00089a017

文献信息

• Additions of malononitrile radicals to alkenes: new examples of 1,2-asymmetric induction in iodine and phenylselenium transfer reactions
  作者：Dennis P. Curran、Gebhard Thoma

  DOI：10.1021/ja00037a080

  日期：1992.5