(E)-3-(spiro[2H-azirine-2,2'-tricyclo[3.3.1.1(3,7)]decane]-3-yl)acrylonitrile | 1226893-35-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-3-(spiro[2H-azirine-2,2'-tricyclo[3.3.1.1(3,7)]decane]-3-yl)acrylonitrile
• 英文别名: (E)-3-spiro[adamantane-2,3'-azirine]-2'-ylprop-2-enenitrile
• CAS: 1226893-35-1
• 化学式: C₁₄H₁₆N₂
• 分子量: 212.294
• InChiKey: DHHARBHMLYJICL-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  36.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  金刚烷双吖丙啶 、 反丁烯二腈 反应 1.0h， 以64%的产率得到trans-spiro[cyclopropane-1,2'-tricyclo[3.3.1.1(3',7')]decane]-2,3-dicarbonitrile
  参考文献：
  名称：

  2H-Azirines from a Concerted Addition of Alkylcarbenes to Nitrile Groups

  摘要：

  Photolysis of aziadamantanos in the presence of fumoronitrile (FN) unexpectedly afforded conjugated 2H-azirines resulting from addition of the carbene to the CN triple bond. This represents the first example of a direct azirine formation starting from an alkylcarbene for which a concerted pathway is postulated. The novel outcome if the reaction is favored by the prior formation of a carbene-alkene complex, a type of adduct that only recently has been described.

  DOI：

  10.1021/ol100703r

文献信息

• 2<i>H</i>-Azirines from a Concerted Addition of Alkylcarbenes to Nitrile Groups
  作者：Wolfgang Knoll、Jean-Luc Mieusset、Vladimir B. Arion、Lothar Brecker、Udo H. Brinker

  DOI：10.1021/ol100703r

  日期：2010.5.21

  Photolysis of aziadamantanos in the presence of fumoronitrile (FN) unexpectedly afforded conjugated 2H-azirines resulting from addition of the carbene to the CN triple bond. This represents the first example of a direct azirine formation starting from an alkylcarbene for which a concerted pathway is postulated. The novel outcome if the reaction is favored by the prior formation of a carbene-alkene complex, a type of adduct that only recently has been described.