3-chloro-5-methylindeno[1,2-b]indol-10(5H)-one | 1449335-54-9

• 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: 3-chloro-5-methylindeno[1,2-b]indol-10(5H)-one
• 英文别名: 3-Chloro-5-methylindeno[1,2-b]indol-10-one
• CAS: 1449335-54-9
• 化学式: C₁₆H₁₀ClNO
• 分子量: 267.714
• InChiKey: JOWQHNUCULYDDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以60 mg的产率得到3-chloro-5-methylindeno[1,2-b]indol-10(5H)-one
  参考文献：
  名称：

  Divergent synthesis of 6H-isoindolo[2,1-a]indol-6-ones and indenoindolones: an investigation of Pd-catalyzed isocyanide insertion

  摘要：

  A novel Pd-catalyzed intramolecular cyclization via tert-butyl isocyanide insertion from 2-(2-bromophenyl)-1H-indoles has been developed, which demonstrates the utility of isocyanides in C-N or C-C bond construction. Treatment of 2-(2-bromophenyl)-1H-indoles with tert-butyl isocyanide affords 6H-isoindolo[2,1-a]indol-6-ones with high efficiency. However, N-methyl or N-Boc protected 2-(2-bromophenyl)-1H-indoles gives indenoindolones in excellent yields under the same condition, which reveals that under the described situation, isocyanides insertion for the formation of C-N bonds is prior to that of C-C bonds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.018

文献信息

• Facile Access to 3-Acylindoles through Palladium-Catalyzed Addition of Indoles to Nitriles: The One-Pot Synthesis of Indenoindolones
  作者：Yuanhong Ma、Jingsong You、Feijie Song

  DOI：10.1002/chem.201203354

  日期：2013.1.21

  The palladium‐catalyzed addition of indoles to nitriles affords 3‐acylindoles. The reaction proceeds with high selectivity, wide substrate scope, broadly available starting materials, and an operationally simple procedure. Combination with the palladium‐catalyzed intramolecular oxidative coupling of 3‐indolylarylketone gives access to indenoindolones in a one‐pot synthesis.

  关联性良好：钯催化的吲哚在腈中的加成反应生成3-acylindoldols。反应以高选择性，广泛的底物范围，广泛可用的起始原料和操作简单的方法进行。与钯催化的3-吲哚基芳基酮的分子内氧化偶合相结合，可在一锅合成中获得茚并吲哚酮。
• Pd-Catalyzed Cyclocarbonylation of 2-(2-Bromoaryl)indoles with CO as a C1 Source: Selective Access to 6 <i>H</i>-Isoindolo[2,1-<i>a</i>]indol-6-ones and Indeno[1,2-<i>b</i>]indol-10(5 <i>H</i>)-ones
  作者：Shenghai Guo、Li Tao、Fang Wang、Xuesen Fan

  DOI：10.1002/asia.201601067

  日期：2016.11.7

  A highly efficient and regioselective synthetic route to 6 H‐isoindolo[2,1‐a]indol‐6‐ones and indeno[1,2‐b]indol‐10(5 H)‐ones through the Pd‐catalyzed cyclocarbonylation of 2‐(2‐bromoaryl)indoles under atmospheric CO pressure has been achieved. Notably, the regioselectivity of the reaction was exclusively dependent on the structural characteristics of the indole substrates. With N‐unsubstituted indoles

  通过2的Pd催化环羰基化反应制得6 H-异吲哚并[2,1- a ]吲哚-6-和茚并[1,2 - b ] indol-10（5  H）-1的高效且区域选择性的合成途径 在大气压CO压力下获得了（2-溴芳基）吲哚。值得注意的是，反应的区域选择性仅取决于吲哚底物的结构特征。以N-未取代的吲哚为起始原料，该反应获得了6 H-异吲哚并[2,1 - a ]吲哚-6-酮，收率为优良。另一方面，以N-取代的吲哚为底物，反应得到茚并[1,2 - b ] indol-10（5  H）-以高度区域选择性的方式进行。