(3S)-3-(4-fluorophenyl)-3-(1H-indol-3-yl)propanal | 1188292-99-0

• 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: (3S)-3-(4-fluorophenyl)-3-(1H-indol-3-yl)propanal
• CAS: 1188292-99-0
• 化学式: C₁₇H₁₄FNO
• 分子量: 267.303
• InChiKey: COWAWXSCDCLQGN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 、 对氟肉桂醛 在 (2S)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 三乙胺 作用下， 以 甲基叔丁基醚 为溶剂， 反应 36.0h， 以80%的产率得到(3S)-3-(4-fluorophenyl)-3-(1H-indol-3-yl)propanal
  参考文献：
  名称：

  α，β-不饱和醛与吲哚不对称Friedel-Crafts烷基化的有效对映选择性方法

  摘要：

  Abstractmagnified imageThe Lewis base‐Lewis base bifunctional catalytic system has been developed and successfully applied to the asymmetric Friedel–Crafts alkylation of indoles with α,β‐unsaturated aldehydes. The reactions are promoted by chiral diphenylprolinol trimethylsilyl ether in the presence of triethylamine. By this protocol, optically active 3‐substituted indoles can be obtained in an organocatalytic process that is free of Lewis or protic acid in high yields with up to 98% ee. Besides, this reaction could be carried out on a gram scale without any loss in the enantioselectivity.

  DOI：

  10.1002/adsc.200800710

文献信息

• An Efficient Enantioselective Method for Asymmetric Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Aldehydes
  作者：Liang Hong、Lei Wang、Chao Chen、Bangzhi Zhang、Rui Wang

  DOI：10.1002/adsc.200800710

  日期：2009.3

  Abstractmagnified imageThe Lewis base‐Lewis base bifunctional catalytic system has been developed and successfully applied to the asymmetric Friedel–Crafts alkylation of indoles with α,β‐unsaturated aldehydes. The reactions are promoted by chiral diphenylprolinol trimethylsilyl ether in the presence of triethylamine. By this protocol, optically active 3‐substituted indoles can be obtained in an organocatalytic process that is free of Lewis or protic acid in high yields with up to 98% ee. Besides, this reaction could be carried out on a gram scale without any loss in the enantioselectivity.