[8-bromo-4-(2-trimethylsilylethoxymethyl)-2,3-dihydro-1H-cyclopenta[b]indol-5-yl]-phenylmethanol | 604788-47-8

• 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: [8-bromo-4-(2-trimethylsilylethoxymethyl)-2,3-dihydro-1H-cyclopenta[b]indol-5-yl]-phenylmethanol
• CAS: 604788-47-8
• 化学式: C₂₄H₃₀BrNO₂Si
• 分子量: 472.497
• InChiKey: SZFJAHOQGNJMSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  34.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [8-bromo-4-(2-trimethylsilylethoxymethyl)-2,3-dihydro-1H-cyclopenta[b]indol-5-yl]-phenylmethanol 在 叔丁基锂 作用下， 以 乙醚 为溶剂， 生成 5-(Hydroxy-phenyl-methyl)-4-(2-trimethylsilanyl-ethoxymethyl)-1,2,3,4-tetrahydro-cyclopenta[b]indole-8-carboxylic acid methyl ester
  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：

  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-trimethylsilylethoxymethyl)-2,3-dihydro-1H-cyclopenta[b]indol-5-yl]-phenylmethanol
  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