5-bromo-1-(tert-butyldimethylsilyl)-6,7,8,9-tetrahydro-1H-6,9-methanobenzo[g]indole-7,8-diol | 1421858-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 5-bromo-1-(tert-butyldimethylsilyl)-6,7,8,9-tetrahydro-1H-6,9-methanobenzo[g]indole-7,8-diol
• CAS: 1421858-24-3
• 化学式: C₁₉H₂₆BrNO₂Si
• 分子量: 408.41
• InChiKey: FEABKWPCEOFIMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  45.39
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-bromo-1-(tert-butyldimethylsilyl)-6,7,8,9-tetrahydro-1H-6,9-methanobenzo[g]indole-7,8-diol 在 sodium tetrahydroborate 、 sodium periodate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 14.25h， 生成 [(6R,8S)-5-bromo-1-[tert-butyl(dimethyl)silyl]-8-(methylsulfonyloxymethyl)-7,8-dihydro-6H-cyclopenta[g]indol-6-yl]methyl methanesulfonate
  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：

  1,2,3-tribromo-5-methyl-4-nitrobenzene 在 四氧化锇 、 正丁基锂 、 iron(III) chloride hexahydrate 、 N-methyl morpholine N-oxide hydrate 、 sodium hydride 、 甲烷 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 10.66h， 生成 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