(6aR,8S,9R,10R,10aR)-8-chloro-9-ethenyl-6,6,9-trimethyl-5,6a,7,8,10,10a-hexahydroindeno[2,1-b]indol-10-amine | 870987-53-4

• 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: (6aR,8S,9R,10R,10aR)-8-chloro-9-ethenyl-6,6,9-trimethyl-5,6a,7,8,10,10a-hexahydroindeno[2,1-b]indol-10-amine
• CAS: 870987-53-4
• 化学式: C₂₀H₂₅ClN₂
• 分子量: 328.885
• InChiKey: FIPGCJOYVQPZTE-YCSGKXEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (6aR,8S,9R,10R,10aR)-8-chloro-9-ethenyl-6,6,9-trimethyl-5,6a,7,8,10,10a-hexahydroindeno[2,1-b]indol-10-amine 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 伯吉斯试剂 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 次氯酸叔丁酯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 1.42h， 生成 (+)-fisherindole I
  参考文献：
  名称：

  Enantioselective Total Syntheses of Welwitindolinone A and Fischerindoles I and G

  摘要：

  The first total syntheses of welwitindolinone A and the most complex members of the fischerindole family, fischerindoles I and G, are reported. Highlights of these short, protecting-group-free syntheses include the application of the recently developed direct indole-carbonyl coupling, a simple approach for installing the quaternary center with neighboring chlorine atom, a regioselective dehydrogenation/dehydration cascade to access fischerindole I, and a remarkably facile oxidative ring contraction to construct welwitindolinone A. An alternative biogenetic hypothesis, whose accuracy is suggested by the success of the current syntheses, is also put forth for this alkaloid family.

  DOI：

  10.1021/ja056171r
• 作为产物：
  描述：

  (6aR,8S,9R,10aR)-8-chloro-9-ethenyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-5H-indeno[2,1-b]indol-10-one 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 168.0h， 以48%的产率得到(6aR,8S,9R,10R,10aR)-8-chloro-9-ethenyl-6,6,9-trimethyl-5,6a,7,8,10,10a-hexahydroindeno[2,1-b]indol-10-amine
  参考文献：
  名称：

  Enantioselective Total Syntheses of Welwitindolinone A and Fischerindoles I and G

  摘要：

  The first total syntheses of welwitindolinone A and the most complex members of the fischerindole family, fischerindoles I and G, are reported. Highlights of these short, protecting-group-free syntheses include the application of the recently developed direct indole-carbonyl coupling, a simple approach for installing the quaternary center with neighboring chlorine atom, a regioselective dehydrogenation/dehydration cascade to access fischerindole I, and a remarkably facile oxidative ring contraction to construct welwitindolinone A. An alternative biogenetic hypothesis, whose accuracy is suggested by the success of the current syntheses, is also put forth for this alkaloid family.

  DOI：

  10.1021/ja056171r

文献信息

• Enantioselective Total Syntheses of Welwitindolinone A and Fischerindoles I and G
  作者：Phil S. Baran、Jeremy M. Richter

  DOI：10.1021/ja056171r

  日期：2005.11.1

  The first total syntheses of welwitindolinone A and the most complex members of the fischerindole family, fischerindoles I and G, are reported. Highlights of these short, protecting-group-free syntheses include the application of the recently developed direct indole-carbonyl coupling, a simple approach for installing the quaternary center with neighboring chlorine atom, a regioselective dehydrogenation/dehydration cascade to access fischerindole I, and a remarkably facile oxidative ring contraction to construct welwitindolinone A. An alternative biogenetic hypothesis, whose accuracy is suggested by the success of the current syntheses, is also put forth for this alkaloid family.