2-[4-(2-Nitrophenyl)-5-oxocyclohex-3-en-1-yl]acetonitrile | 1414860-52-8

• 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: 2-[4-(2-Nitrophenyl)-5-oxocyclohex-3-en-1-yl]acetonitrile
• 英文别名: 2-[4-(2-nitrophenyl)-5-oxocyclohex-3-en-1-yl]acetonitrile
• CAS: 1414860-52-8
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: RBBAOKPRZLJMSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4-(2-Nitrophenyl)-5-oxocyclohex-3-en-1-yl]acetonitrile 在 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 66.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以87%的产率得到2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)ethan-1-amine
  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：

  methyl 2-cyano-2-(3-oxocyclohexyl)acetate 在 吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 水 、 碘 、 铜 、 对甲苯磺酸 、 lithium chloride 、 2-碘酰基苯甲酸 作用下， 以 氯仿 、 二甲基亚砜 、 甲苯 为溶剂， 生成 2-[4-(2-Nitrophenyl)-5-oxocyclohex-3-en-1-yl]acetonitrile
  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.