3-ethoxycarbonyl-3-(5-methoxy-1H-indol-3-yl)isoindolin-1-one | 1423160-20-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-ethoxycarbonyl-3-(5-methoxy-1H-indol-3-yl)isoindolin-1-one
• 英文别名: ethyl 1-(5-methoxy-1H-indol-3-yl)-3-oxo-2H-isoindole-1-carboxylate
• CAS: 1423160-20-6
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: AGSSXNNMJYIRLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 1-羟基-3-氧代-2H-异吲哚-1-羧酸乙酯 在 D(+)-10-樟脑磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 以88%的产率得到3-ethoxycarbonyl-3-(5-methoxy-1H-indol-3-yl)isoindolin-1-one
  参考文献：
  名称：

  (±)-CSA catalyzed Friedel–Crafts alkylation of indoles with 3-ethoxycarbonyl-3-hydoxyisoindolin-1-one: an easy access of 3-ethoxycarbonyl-3-indolylisoindolin-1-ones bearing a quaternary α-amino acid moiety

  摘要：

  For the first time, a very simple, efficient, mild, catalytic, and one-step procedure for the synthesis of a series of new 3-ethoxycarbonyl-3-indolylsubstituted-isoindol-1-one derivatives has been achieved via a Friedel-Crafts alkylation of indoles with 3-hydroxy-3-ethoxycarbonylisoindolin-1-one at room temperature using easily available inexpensive camphor-10-sulfonic acid as an organocatalyst. The current protocol provides good to excellent yields of the title compounds with high substrate scope. In addition, the desired product possesses a chiral quaternary carbon center at the 3-position on isoindolin-1-one ring which is flanked by indole moiety, amino and ester groups for further elaborations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.010

文献信息

• (±)-CSA catalyzed Friedel–Crafts alkylation of indoles with 3-ethoxycarbonyl-3-hydoxyisoindolin-1-one: an easy access of 3-ethoxycarbonyl-3-indolylisoindolin-1-ones bearing a quaternary α-amino acid moiety
  作者：Anvita Srivastava、Shivendra Singh、Sampak Samanta

  DOI：10.1016/j.tetlet.2013.01.010

  日期：2013.3

  For the first time, a very simple, efficient, mild, catalytic, and one-step procedure for the synthesis of a series of new 3-ethoxycarbonyl-3-indolylsubstituted-isoindol-1-one derivatives has been achieved via a Friedel-Crafts alkylation of indoles with 3-hydroxy-3-ethoxycarbonylisoindolin-1-one at room temperature using easily available inexpensive camphor-10-sulfonic acid as an organocatalyst. The current protocol provides good to excellent yields of the title compounds with high substrate scope. In addition, the desired product possesses a chiral quaternary carbon center at the 3-position on isoindolin-1-one ring which is flanked by indole moiety, amino and ester groups for further elaborations. (C) 2013 Elsevier Ltd. All rights reserved.