[10-bromo-5,15-diphenylporphyrinato]-magnesium(II) | 1415023-88-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: [10-bromo-5,15-diphenylporphyrinato]-magnesium(II)
• CAS: 1415023-88-9
• 化学式: C₃₂H₁₉BrMgN₄
• 分子量: 563.739
• InChiKey: CZQXXKVELAVDFV-TVGBRLMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  [10-bromo-5,15-diphenylporphyrinato]-magnesium(II) 、 (三甲基硅基)甲基氯化镁 在 tris-(dibenzylideneacetone)dipalladium(0) 、 Diphenylphosphine oxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以91%的产率得到[5,15-diphenyl-10-(trimethylsilyl)methylporphyrinato]-magnesium(II)
  参考文献：
  名称：

  Palladium-catalyzed Kumada Coupling Reaction of Bromoporphyrins with Silylmethyl Grignard Reagents: Preparation of Silylmethyl-substituted Porphyrins as a Multipurpose Synthon for Fabrication of Porphyrin Systems

  摘要：

  We have developed an efficient method for preparing silylmethyl-substituted porphyrins via the palladium-catalyzed Kumada cross-coupling reaction of bromoporphyrins with silylmethyl Grignard reagents. We demonstrated the synthetic utility of these silylmethylporphyrins as a multipurpose synthon for fabricating porphyrin derivatives through a variety of transformations of the silylmethyl groups, including the DDQ-promoted oxidative conversion to CHO, CH2OH, CH2OMe, and CH2F functionalities and the fluoride ion-mediated desilylative introduction of carbon-carbon single and double bonds.

  DOI：

  10.1021/jo302122f
• 作为产物：
  描述：

  5-bromo-10,20-diphenylporphyrin 在 magnesium bromide ethyl etherate 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以98%的产率得到[10-bromo-5,15-diphenylporphyrinato]-magnesium(II)
  参考文献：
  名称：

  Palladium-catalyzed Kumada Coupling Reaction of Bromoporphyrins with Silylmethyl Grignard Reagents: Preparation of Silylmethyl-substituted Porphyrins as a Multipurpose Synthon for Fabrication of Porphyrin Systems

  摘要：

  We have developed an efficient method for preparing silylmethyl-substituted porphyrins via the palladium-catalyzed Kumada cross-coupling reaction of bromoporphyrins with silylmethyl Grignard reagents. We demonstrated the synthetic utility of these silylmethylporphyrins as a multipurpose synthon for fabricating porphyrin derivatives through a variety of transformations of the silylmethyl groups, including the DDQ-promoted oxidative conversion to CHO, CH2OH, CH2OMe, and CH2F functionalities and the fluoride ion-mediated desilylative introduction of carbon-carbon single and double bonds.

  DOI：

  10.1021/jo302122f