methyl 3-(1H-indol-3-yl)-2,2-dimethylpropanoate

• 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: methyl 3-(1H-indol-3-yl)-2,2-dimethylpropanoate
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: NPMGIBADGFDRJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚-3-甲醇 、 1-甲氧基-1-(三甲基甲硅氧基)-2-甲基-1-丙烯 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以76%的产率得到methyl 3-(1H-indol-3-yl)-2,2-dimethylpropanoate
  参考文献：
  名称：

  Synthesis of β-heteroaryl propionates via trapping of carbocations with π-nucleophiles

  摘要：

  A variety of heterocyclic alcohols and acetates were Coupled with silyl ketene acetals and other pi-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate to provide an array Of Substituted beta-heteroaryl propionates, including those with contiguous quaternary centers, as well as vinylogs thereof. This reaction also proceeds with high diastereoselectivity when the pi-nucleophile bears a chiral auxiliary. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.018

文献信息

• Magnesium trifluoromethanesulfonimide(triflimide) promoted substitution reactions of allylic and benzylic acetates. Magnesium triflimide as a substitute for magnesium perchlorate
  作者：Paul A. Grieco、Scott T. Handy

  DOI：10.1016/s0040-4039(97)00441-3

  日期：1997.4

  Magnesium triflimide(10 mol% in methylene chloride) is a convenient catalyst for the nucleophilic substitution of allylic and benzylic acetates, and constitutes a useful alternative to magnesium perchlorate. (C) 1997 Elsevier Science Ltd.
• US7205324B2
  申请人：——

  公开号：US7205324B2

  公开（公告）日：2007-04-17
• US7355053B2
  申请人：——

  公开号：US7355053B2

  公开（公告）日：2008-04-08
• Synthesis of β-heteroaryl propionates via trapping of carbocations with π-nucleophiles
  作者：Tsung-hao Fu、Amy Bonaparte、Stephen F. Martin

  DOI：10.1016/j.tetlet.2009.02.018

  日期：2009.7

  A variety of heterocyclic alcohols and acetates were Coupled with silyl ketene acetals and other pi-nucleophiles in the presence of trimethylsilyl trifluoromethanesulfonate to provide an array Of Substituted beta-heteroaryl propionates, including those with contiguous quaternary centers, as well as vinylogs thereof. This reaction also proceeds with high diastereoselectivity when the pi-nucleophile bears a chiral auxiliary. (C) 2009 Elsevier Ltd. All rights reserved.