9'-methyl-1',9'-dihydrospiro[isoindoline-1,4'-pyrido[3,4-b]indole]-3,3'(2'H)-dione | 1423160-28-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 9'-methyl-1',9'-dihydrospiro[isoindoline-1,4'-pyrido[3,4-b]indole]-3,3'(2'H)-dione
• CAS: 1423160-28-4
• 化学式: C₁₉H₁₅N₃O₂
• 分子量: 317.347
• InChiKey: NJDMRUMEMQEQQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.13
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-ethoxycarbonyl-3-(1-methyl-2-azidomethylindol-3-yl)isoindolin-1-one 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以27%的产率得到9'-methyl-1',9'-dihydrospiro[isoindoline-1,4'-pyrido[3,4-b]indole]-3,3'(2'H)-dione
  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