tert-butyl 5-bromo-3-((tert-butyldimethylsilylroxy)methyl)-1H-indole-1-carboxylate | 905710-15-8

• 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: tert-butyl 5-bromo-3-((tert-butyldimethylsilylroxy)methyl)-1H-indole-1-carboxylate
• CAS: 905710-15-8
• 化学式: C₂₀H₃₀BrNO₃Si
• 分子量: 440.453
• InChiKey: UILBHQCIEXKFCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.71
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-bromo-3-((tert-butyldimethylsilylroxy)methyl)-1H-indole-1-carboxylate 、 a-叠氮基-苯乙酸甲酯 在 dirhodium(II) tetrakis[(S)-N-phthaloyl-tert-leucinate] 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 生成 tert-butyl 5-bromo-3-((1R,2R)-1-(tert-butyldimethylsilyloxy)-3-methoxy-3-oxo-2-phenylpropyl)-1H-indole-1-carboxylate 、 tert-butyl 5-bromo-3-(1-(tert-butyldimethylsilyloxy)-3-methoxy-3-oxo-2-phenylpropyl)-1H-indole-1-carboxylate 、 tert-butyl 5-bromo-3-(1-(tert-butyldimethylsilyloxy)-3-methoxy-3-oxo-2-phenylpropyl)-1H-indole-1-carboxylate 、 tert-butyl 5-bromo-3-((1S,2S)-1-(tert-butyldimethylsilyloxy)-3-methoxy-3-oxo-2-phenylpropyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Investigation into Factors Influencing Stereoselectivity in the Reactions of Heterocycles with Donor−Acceptor-Substituted Rhodium Carbenoids

  摘要：

  Rhodium-catalyzed decomposition of aryldiazoacetates in the presence of pyrroles or furans results in mono- or biscyclopropanation of the heterocycle, but with opposite enantioinduction. In the absence of sterically encumbering groups, the cyclopropanation of furan occurs with initial bond formation at the 2-position. If this pathway is sterically blocked, cyclopropanation can occur with initial bond formation at the 3-position of the furan ring; in this case, the cyclopropanation reaction takes place on the opposite face of the heterocycle, and the opposite enantioinduction is observed. Upon extension of this methodology to benzofurans, a highly enantioselective monocyclopropanation reaction occurs to furnish a product derived from initial bond formation at the 2-position of the benzofuran. When this reaction pathway is inhibited by sterically encumbering substituents on the benzofuran, no cyclopropanation of the furan ring is observed, and instead, double cyclopropanation of the benzene ring occurs. Double cyclopropanation of the benzene ring was also observed in reactions with indoles.

  DOI：

  10.1021/jo060779g
• 作为产物：
  描述：

  5-溴-3-甲酰基吲哚-1-羧酸叔丁酯 在 咪唑 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 tert-butyl 5-bromo-3-((tert-butyldimethylsilylroxy)methyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Investigation into Factors Influencing Stereoselectivity in the Reactions of Heterocycles with Donor−Acceptor-Substituted Rhodium Carbenoids

  摘要：

  Rhodium-catalyzed decomposition of aryldiazoacetates in the presence of pyrroles or furans results in mono- or biscyclopropanation of the heterocycle, but with opposite enantioinduction. In the absence of sterically encumbering groups, the cyclopropanation of furan occurs with initial bond formation at the 2-position. If this pathway is sterically blocked, cyclopropanation can occur with initial bond formation at the 3-position of the furan ring; in this case, the cyclopropanation reaction takes place on the opposite face of the heterocycle, and the opposite enantioinduction is observed. Upon extension of this methodology to benzofurans, a highly enantioselective monocyclopropanation reaction occurs to furnish a product derived from initial bond formation at the 2-position of the benzofuran. When this reaction pathway is inhibited by sterically encumbering substituents on the benzofuran, no cyclopropanation of the furan ring is observed, and instead, double cyclopropanation of the benzene ring occurs. Double cyclopropanation of the benzene ring was also observed in reactions with indoles.

  DOI：

  10.1021/jo060779g