7-Bromo-2-(tert-butyl)isoindolin-1-one | 1290140-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 7-Bromo-2-(tert-butyl)isoindolin-1-one
• 英文别名: 7-bromo-2-tert-butyl-3H-isoindol-1-one
• CAS: 1290140-02-1
• 化学式: C₁₂H₁₄BrNO
• 分子量: 268.153
• InChiKey: DFLNBDDHXJLWRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(3-溴苄基)-2-甲基-2-丙胺 在 过氧化双月桂酰 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 4.25h， 生成 5-bromo-2-tert-butylisoindolin-1-one 、 7-Bromo-2-(tert-butyl)isoindolin-1-one
  参考文献：
  名称：

  Convenient access to isoindolinones via carbamoyl radical cyclization. Synthesis of cichorine and 4-hydroxyisoindolin-1-one natural products

  摘要：

  An efficient and convenient access to 2-tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert-butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its cyclization to the aromatic system, and the dilauroyl peroxide (DLP) mediated rearomatization to generate the isoindolinone ring system. Additionally, the syntheses of cichorine and 4-hydroxyisoindolin-1-one natural products were carried out to underscore the synthetic potential of this xanthate-based carbamoyl radical-oxidative cyclization. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.003

文献信息

• Convenient access to isoindolinones via carbamoyl radical cyclization. Synthesis of cichorine and 4-hydroxyisoindolin-1-one natural products
  作者：Germán López-Valdez、Simón Olguín-Uribe、Alejandra Millan-Ortíz、Rocio Gamez-Montaño、Luis D. Miranda

  DOI：10.1016/j.tet.2011.01.003

  日期：2011.4

  An efficient and convenient access to 2-tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert-butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its cyclization to the aromatic system, and the dilauroyl peroxide (DLP) mediated rearomatization to generate the isoindolinone ring system. Additionally, the syntheses of cichorine and 4-hydroxyisoindolin-1-one natural products were carried out to underscore the synthetic potential of this xanthate-based carbamoyl radical-oxidative cyclization. (C) 2011 Elsevier Ltd. All rights reserved.