5-bromo-1-(tert-butyldimethylsilyl)-6,9-dihydro-1H-6,9-methanobenzo[g]indole | 1421858-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-bromo-1-(tert-butyldimethylsilyl)-6,9-dihydro-1H-6,9-methanobenzo[g]indole
• 英文别名: (9-Bromo-4-azatetracyclo[9.2.1.02,10.03,7]tetradeca-2,5,7,9,12-pentaen-4-yl)-tert-butyl-dimethylsilane
• CAS: 1421858-20-9
• 化学式: C₁₉H₂₄BrNSi
• 分子量: 374.396
• InChiKey: NETONIOVXRFXKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5-bromo-1-(tert-butyldimethylsilyl)-6,9-dihydro-1H-6,9-methanobenzo[g]indole 在 四氧化锇 、 N-methyl morpholine N-oxide hydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以75%的产率得到5-bromo-1-(tert-butyldimethylsilyl)-6,7,8,9-tetrahydro-1H-6,9-methanobenzo[g]indole-7,8-diol
  参考文献：
  名称：

  Total synthesis of (±)-cis-trikentrin B via intermolecular 6,7-indole aryne cycloaddition and Stille cross-coupling

  摘要：

  An efficient total synthesis of the annulated indole natural product(+/-)-cis-trikentrin B was accomplished by means of a regioselectively generated 6,7-indole aryne cycloaddition via selective metal-halogen exchange from a 5,6,7-tribromoindole. The unaffected C-5 bromine was subsequently used for a Stille cross-coupling to install the butenyl side chain and complete the synthesis. This strategy provides rapid access into the trikentrins and the related herbindoles, and represents another application of this methodology to natural products total synthesis. The required 5,6,7-indole aryne precursor was prepared using the Leimgruber-Batcho indole synthesis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.125
• 作为产物：
  描述：

  5,6,7-tribromoindole 在 正丁基锂 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 1.08h， 生成 5-bromo-1-(tert-butyldimethylsilyl)-6,9-dihydro-1H-6,9-methanobenzo[g]indole
  参考文献：
  名称：

  Total synthesis of (±)-cis-trikentrin B via intermolecular 6,7-indole aryne cycloaddition and Stille cross-coupling

  摘要：

  An efficient total synthesis of the annulated indole natural product(+/-)-cis-trikentrin B was accomplished by means of a regioselectively generated 6,7-indole aryne cycloaddition via selective metal-halogen exchange from a 5,6,7-tribromoindole. The unaffected C-5 bromine was subsequently used for a Stille cross-coupling to install the butenyl side chain and complete the synthesis. This strategy provides rapid access into the trikentrins and the related herbindoles, and represents another application of this methodology to natural products total synthesis. The required 5,6,7-indole aryne precursor was prepared using the Leimgruber-Batcho indole synthesis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.125