spiro[2H-indole-2-cyclohexane]-3(1H)-imine | 240486-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: spiro[2H-indole-2-cyclohexane]-3(1H)-imine
• 英文别名: spiro[1H-indole-2,1'-cyclohexane]-3-imine
• CAS: 240486-19-5
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: KHULBXLXOQEQFM-UHFFFAOYSA-N

物化性质

• 熔点：
  40-41 °C
• 沸点：
  373.3±35.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  spiro[2H-indole-2-cyclohexane]-3(1H)-imine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到spiro[cyclohexane-1,2'-indolin]-3'-one
  参考文献：
  名称：

  Conformational Switching and the Synthesis of Spiro[2H-indol]-3(1H)-ones by Radical Cyclization

  摘要：

  Radical cyclization of 1-(2-bromophenylamino)cyclohexanecarbonitriles (3, X = CH) and 4-(2-bromophenylamino)-4-piperidinecarbonitriles (3, X = N) provide spiro[2H-indole-2-cyclohexan]3(1H)-imines (5, X = CH) and spiro[2H-indole-2,4'-piperidin]-3(1H)-imines (5, X = N), respectively, in 33-57% yields. This contradicts a recent report that 1-(2-bromophenylamino)cyclohexane-carbonitrile (3, X-R-2 = CH2), treated under apparently identical conditions, led only to nitrile transfer product 6 (X-R-2 = CH2). Acidic hydrolyses of the imines provide the corresponding ketones 2 in quantitative yields. Single-crystal X-ray analyses of ketone 2e and nitrile 3e indicate that the relative configuration of the aromatic nitrogen has been inverted during the cyclization. In addition, NOE NMR analyses of spiroindolepiperidine 2e and its aniline-nitrogen-methylated analogue 10a show that the relative conformation of the piperidine ring has inverted. Thus, methylation of 2c acts as a conformational "switch" for the spiroindolepiperidine ring system.

  DOI：

  10.1021/jo970105t
• 作为产物：
  描述：

  环己酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 49.0h， 生成 spiro[2H-indole-2-cyclohexane]-3(1H)-imine
  参考文献：
  名称：

  Conformational Switching and the Synthesis of Spiro[2H-indol]-3(1H)-ones by Radical Cyclization

  摘要：

  Radical cyclization of 1-(2-bromophenylamino)cyclohexanecarbonitriles (3, X = CH) and 4-(2-bromophenylamino)-4-piperidinecarbonitriles (3, X = N) provide spiro[2H-indole-2-cyclohexan]3(1H)-imines (5, X = CH) and spiro[2H-indole-2,4'-piperidin]-3(1H)-imines (5, X = N), respectively, in 33-57% yields. This contradicts a recent report that 1-(2-bromophenylamino)cyclohexane-carbonitrile (3, X-R-2 = CH2), treated under apparently identical conditions, led only to nitrile transfer product 6 (X-R-2 = CH2). Acidic hydrolyses of the imines provide the corresponding ketones 2 in quantitative yields. Single-crystal X-ray analyses of ketone 2e and nitrile 3e indicate that the relative configuration of the aromatic nitrogen has been inverted during the cyclization. In addition, NOE NMR analyses of spiroindolepiperidine 2e and its aniline-nitrogen-methylated analogue 10a show that the relative conformation of the piperidine ring has inverted. Thus, methylation of 2c acts as a conformational "switch" for the spiroindolepiperidine ring system.

  DOI：

  10.1021/jo970105t