(2R)-2-(1H-indol-3-yl)-2-phenyl-ethylamine | 871828-99-8

• 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: (2R)-2-(1H-indol-3-yl)-2-phenyl-ethylamine
• 英文别名: 2-(1H-indol-3-yl)-2-phenylethan-1-amine；3-(1H-indol-3-yl)-3-phenylethanamine；2-(1H-indol-3-yl)-2-phenylethanamine；(2R)-2-(1H-indol-3-yl)-2-phenylethanamine
• CAS: 871828-99-8
• 化学式: C₁₆H₁₆N₂
• mdl: MFCD01567108
• 分子量: 236.316
• InChiKey: HEBVBIGUNHPPLF-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (2R)-2-(1H-indol-3-yl)-2-phenyl-ethylamine 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 N-[(2R)-2-(1H-indol-3-yl)-2-phenyl-ethyl]-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  通过使用简单的硫脲有机催化剂，将硝基苯与吲哚进行催化对映选择性弗里德-克来福特烷基化。

  摘要：

  DOI：

  10.1002/anie.200500227
• 作为产物：
  描述：

  3-((1R)-2-nitro-1-phenylethyl)-1H-indole 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 生成 (2R)-2-(1H-indol-3-yl)-2-phenyl-ethylamine
  参考文献：
  名称：

  通过使用简单的硫脲有机催化剂，将硝基苯与吲哚进行催化对映选择性弗里德-克来福特烷基化。

  摘要：

  DOI：

  10.1002/anie.200500227

文献信息

• Cu(I)-Catalyzed Enantioselective Friedel–Crafts Alkylation of Indoles with 2-Aryl-<i>N</i>-sulfonylaziridines as Alkylating Agents
  作者：Chen Ge、Ren-Rong Liu、Jian-Rong Gao、Yi-Xia Jia

  DOI：10.1021/acs.orglett.6b01317

  日期：2016.7.1

  A highly enantioselective Friedel–Crafts alkylation of indoles with N-sulfonylaziridines as alkylating agents has been developed by utilizing the complex of Cu(CH3CN)4BF4/(S)-Segphos as a catalyst. A range of optically active tryptamine derivatives are obtained in good to excellent yields and enantioselectivities (up to >99% ee) via a kinetic resolution process.

  通过使用Cu（CH 3 CN）4 BF 4 /（S）-Segphos的配合物，开发了一种以N-磺酰基氮丙啶为烷基化剂的吲哚类高对映选择性的Friedel-Crafts烷基化方法。通过动力学拆分方法以良好至极好的收率和对映选择性（高达> 99％ee）获得了一系列旋光性色胺。
• 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.