2-(5-Oxocyclohex-3-en-1-yl)prop-2-enenitrile | 1414860-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(5-Oxocyclohex-3-en-1-yl)prop-2-enenitrile
• 英文别名: 2-(5-oxocyclohex-3-en-1-yl)prop-2-enenitrile
• CAS: 1414860-57-3
• 化学式: C₉H₉NO
• 分子量: 147.177
• InChiKey: UFWCZORDUAAFIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(5-Oxocyclohex-3-en-1-yl)prop-2-enenitrile 在 吡啶 、 碘 作用下， 以 氯仿 为溶剂， 以75%的产率得到2-(4-Iodo-5-oxocyclohex-3-en-1-yl)prop-2-enenitrile
  参考文献：
  名称：

  A Raney-Cobalt-Mediated Tandem Reductive Cyclization Route to the 1,5-Methanoazocino[4,3-b]indole Framework of the Uleine and Strychnos Alkaloids

  摘要：

  The readily accessible enones 8, 17, and 18 undergo 2-fold reductive cyclization reactions upon exposure to hydrogen in the presence of Raney-cobalt and thereby afford compounds 11 (72%), 19 (47%), and 20 (84%), respectively. These products embody the ABCD-ring system associated with the title alkaloids, and compound 11 Can be converted, over four steps and in 33% yield, into congener 24 incorporating the ABCDE-ring system of the Strychnos alkaloids.

  DOI：

  10.1021/jo302132d
• 作为产物：
  描述：

  2-cyano-2-(3-oxocyclohexyl)acetic acid 在 聚合甲醛 、 对甲苯磺酸 、 二乙胺 、 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 、 乙酸乙酯 、 甲苯 为溶剂， 反应 19.0h， 生成 2-(5-Oxocyclohex-3-en-1-yl)prop-2-enenitrile
  参考文献：
  名称：

  A Raney-Cobalt-Mediated Tandem Reductive Cyclization Route to the 1,5-Methanoazocino[4,3-b]indole Framework of the Uleine and Strychnos Alkaloids

  摘要：

  The readily accessible enones 8, 17, and 18 undergo 2-fold reductive cyclization reactions upon exposure to hydrogen in the presence of Raney-cobalt and thereby afford compounds 11 (72%), 19 (47%), and 20 (84%), respectively. These products embody the ABCD-ring system associated with the title alkaloids, and compound 11 Can be converted, over four steps and in 33% yield, into congener 24 incorporating the ABCDE-ring system of the Strychnos alkaloids.

  DOI：

  10.1021/jo302132d

文献信息

• A Raney-Cobalt-Mediated Tandem Reductive Cyclization Route to the 1,5-Methanoazocino[4,3-<i>b</i>]indole Framework of the Uleine and <i>Strychnos</i> Alkaloids
  作者：Tristan A. Reekie、Martin G. Banwell、Anthony C. Willis

  DOI：10.1021/jo302132d

  日期：2012.12.7

  The readily accessible enones 8, 17, and 18 undergo 2-fold reductive cyclization reactions upon exposure to hydrogen in the presence of Raney-cobalt and thereby afford compounds 11 (72%), 19 (47%), and 20 (84%), respectively. These products embody the ABCD-ring system associated with the title alkaloids, and compound 11 Can be converted, over four steps and in 33% yield, into congener 24 incorporating the ABCDE-ring system of the Strychnos alkaloids.