(R)-ethyl 2-ethoxycarbonyl-3-[3-(7-methylindolyl)]-3-phenylpropanoate | 668463-97-6

• 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: (R)-ethyl 2-ethoxycarbonyl-3-[3-(7-methylindolyl)]-3-phenylpropanoate
• 英文别名: ethyl 2-ethoxycarbonyl-3-[3-(7-methylindolyl)]-3-phenyl-propanoate；diethyl 2-[(R)-(7-methyl-1H-indol-3-yl)-phenylmethyl]propanedioate
• CAS: 668463-97-6
• 化学式: C₂₃H₂₅NO₄
• 分子量: 379.456
• InChiKey: SCMITTZYRYKLJH-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-甲基吲哚 、 亚苯甲基丙二酸二乙酯 在 C₄₆H₅₀N₄O₄S₂ 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 异丁醇 为溶剂， 以81%的产率得到
  参考文献：
  名称：

  Cu(OTf)₂-Catalyzed Asymmetric Friedel–Crafts Alkylation Reaction of Indoles with Arylidene Malonates Using Bis(sulfonamide)-Diamine Ligands

  摘要：

  highly efficient Cu-catalyzed asymmetric Friedel Crafts alkylation reaction of indoles with arylidene malonates using simple, stable, and easily prepared bis-sulfonamide diamine ligands was developed. The desired products were obtained in up to 99% yield with 96% ee.

  DOI：

  10.1021/jo400747d

文献信息

• 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.
• Cu(OTf)₂-Catalyzed Asymmetric Friedel–Crafts Alkylation Reaction of Indoles with Arylidene Malonates Using Bis(sulfonamide)-Diamine Ligands
  作者：Jing Wu、Dongping Wang、Fan Wu、Boshun Wan

  DOI：10.1021/jo400747d

  日期：2013.6.7

  highly efficient Cu-catalyzed asymmetric Friedel Crafts alkylation reaction of indoles with arylidene malonates using simple, stable, and easily prepared bis-sulfonamide diamine ligands was developed. The desired products were obtained in up to 99% yield with 96% ee.