(1R,5R)-1,5-diphenyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole | 1146217-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Pyrroloazepines
• 英文名称: (1R,5R)-1,5-diphenyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole
• CAS: 1146217-54-0
• 化学式: C₂₄H₂₂N₂
• 分子量: 338.452
• InChiKey: HFAFIYFUBCAVNW-AUSIDOKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-(1H-indol-3-yl)-3-phenylpropan-1-amine 、 苯甲醛 在 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以44%的产率得到(1R,5R)-1,5-diphenyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole
  参考文献：
  名称：

  N，N'-二氧化物-Scan（III）配合物催化吲哚的对映选择性Friedel-Crafts烷基与丙二烯丙二酸酯的烷基化：不对称合成β-咔啉

  摘要：

  通过使用手性N，N'-二氧化物-Sc（OTf）3络合物作为催化剂，开发了一种有效的亚吲哚丙二酸酯催化吲哚的不对称Friedel-Crafts烷基化反应（参见方案）。已经合成了一些含有吲哚骨架的旋光中间体，例如吲哚丙酸，色胺和β-咔啉。X射线结构分析揭示了atom原子与手性N，N'-二氧化物之间的配位关系。

  DOI：

  10.1002/chem.200802210

文献信息

• Enantioselective Friedel-Crafts Alkylation of Indoles with Alkylidene Malonates Catalyzed by<i>N,N′</i>-Dioxide-Scandium(III) Complexes: Asymmetric Synthesis of<i>β</i>-Carbolines
  作者：Yanling Liu、Deju Shang、Xin Zhou、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/chem.200802210

  日期：2009.2.16

  efficient catalytic asymmetric Friedel–Crafts alkylation of indoles with alkylidene malonates has been developed by using a chiral N,N′‐dioxide–Sc(OTf)3 complex as the catalyst (see scheme). Some optically active intermediates containing the indole skeleton have been synthesized, such as indolepropionic acid, tryptamines, and β‐carbolines. The coordination between the scandium atom and the chiral N,N′‐dioxide

  通过使用手性N，N'-二氧化物-Sc（OTf）3络合物作为催化剂，开发了一种有效的亚吲哚丙二酸酯催化吲哚的不对称Friedel-Crafts烷基化反应（参见方案）。已经合成了一些含有吲哚骨架的旋光中间体，例如吲哚丙酸，色胺和β-咔啉。X射线结构分析揭示了atom原子与手性N，N'-二氧化物之间的配位关系。
• N,N′-Dioxide–scandium(III) complex catalyzed highly enantioselective Friedel–Crafts alkylation of indole to alkylidene malonates
  作者：Yanling Liu、Xin Zhou、Deju Shang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1016/j.tet.2009.12.032

  日期：2010.2

  A highly efficient enantioselective Friedel-Crafts alkylation of indoles with alkylidene malonates has been developed using chiral N,N'-dioxide LA-scandium(III) complex as the catalyst, giving the corresponding products in high yields with excellent enantioselectivities (up to 99% yield and 95% ee). The product 3a was facilely converted into several interesting compounds, such as tryptamines, indolepropionic acids and beta-carbolines. It is noteworthy that the seven-membered beta-carboline-like compound has been synthesized for the first time. Based on the crystal structure of the chiral N,N'-dioxide L10-scandium(III) complex, the proposed transition state and possible catalytic cycle were presented to elucidate the reaction mechanism. (C) 2009 Elsevier Ltd. All rights reserved.