5,8-Dibromo-1,2,3,4-tetrahydro-cyclopenta[b]indole | 604788-28-5

• 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: 5,8-Dibromo-1,2,3,4-tetrahydro-cyclopenta[b]indole
• 英文别名: 5,8-Dibromo-1,2,3,4-tetrahydrocyclopenta[b]indole
• CAS: 604788-28-5
• 化学式: C₁₁H₉Br₂N
• 分子量: 315.007
• InChiKey: CSVWNNGGDAGTEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5,8-Dibromo-1,2,3,4-tetrahydro-cyclopenta[b]indole 在 叔丁基锂 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 8-Bromo-4-(2-trimethylsilanyl-ethoxymethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole
  参考文献：
  名称：

  Synthesis of substituted indoles via a highly selective 7-lithiation of 4,7-dibromoindoles and the effect of indole-nitrogen on regioselectivity

  摘要：

  We have developed an efficient synthetic pathway to rapidly access 4-bromoindoles, 4-substituted indoles, 4-bromo-7-substituted indoles, and 4,7-disubstituted indoles using a highly selective lithiation at the 7-position of 1-alkyl-4,7-dibromoindoles when treated with t-BuLi in ether. Based upon the selectivity obtained with 5,7-dibromoindoles in our previous study and with 4,7-dibromoindoles in the current study, we conclude that the alkylated indole nitrogen plays an important role in controlling selectivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01482-5
• 作为产物：
  描述：

  (2,5-二溴苯基)肼 、 环戊酮 在 boron trifluoride diacetate 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以83%的产率得到5,8-Dibromo-1,2,3,4-tetrahydro-cyclopenta[b]indole
  参考文献：
  名称：

  Synthesis of substituted indoles via a highly selective 7-lithiation of 4,7-dibromoindoles and the effect of indole-nitrogen on regioselectivity

  摘要：

  We have developed an efficient synthetic pathway to rapidly access 4-bromoindoles, 4-substituted indoles, 4-bromo-7-substituted indoles, and 4,7-disubstituted indoles using a highly selective lithiation at the 7-position of 1-alkyl-4,7-dibromoindoles when treated with t-BuLi in ether. Based upon the selectivity obtained with 5,7-dibromoindoles in our previous study and with 4,7-dibromoindoles in the current study, we conclude that the alkylated indole nitrogen plays an important role in controlling selectivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01482-5