isobutyl 2-(2-bromophenyl)-2-diazoacetate | 1632260-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: isobutyl 2-(2-bromophenyl)-2-diazoacetate
• 英文别名: 2-Methylpropyl 2-(2-bromophenyl)-2-diazoacetate
• CAS: 1632260-40-2
• 化学式: C₁₂H₁₃BrN₂O₂
• 分子量: 297.151
• InChiKey: JUKKGBMVLNBPSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isobutyl 2-(2-bromophenyl)-2-diazoacetate 在 rhodium(II) acetate dimer 作用下， 以 苯 为溶剂， 反应 3.5h， 生成 trans-3-(2-bromophenyl)-4-propyloxetane-2-one
  参考文献：
  名称：

  Regioselectivity of Intramolecular Rhodium-Catalyzed C–H Insertion Reactions of α-Aryl-α-diazocarboxylates: Influence of the Aryl Substituent

  摘要：

  It was found that alpha-aryl-alpha-diazocarboxylates react with variable regioselectivity in intramolecular rhodium-catalyzed C-H insertion reactions. 3-(Trialkoxysilyl)propyl esters underwent a clean cis-gamma-lactone formation (62-69%) if the aryl rest was a phenyl group while the analogous alpha-(2-bromophenyl)-alpha-diazocarboxylates produced the respective beta-lactones. In general beta-lactone formation was shown to be the only detectable C-H insertion pathway for the latter substrate class irrespective of the ester substituent. The beta-lactone products (eight examples) were obtained in yields of 41-68% with a diastereomeric ratio (dr) of 75:25 to 96:4 in favor of the trans diastereoisomer. The 2-bromo substituent could be displaced by an aryl group in a subsequent Suzuki cross-coupling reaction.

  DOI：

  10.1055/s-0033-1341062
• 作为产物：
  描述：

  isobutyl 2-(2-bromophenyl)acetate 在 对甲苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 生成 isobutyl 2-(2-bromophenyl)-2-diazoacetate
  参考文献：
  名称：

  Regioselectivity of Intramolecular Rhodium-Catalyzed C–H Insertion Reactions of α-Aryl-α-diazocarboxylates: Influence of the Aryl Substituent

  摘要：

  It was found that alpha-aryl-alpha-diazocarboxylates react with variable regioselectivity in intramolecular rhodium-catalyzed C-H insertion reactions. 3-(Trialkoxysilyl)propyl esters underwent a clean cis-gamma-lactone formation (62-69%) if the aryl rest was a phenyl group while the analogous alpha-(2-bromophenyl)-alpha-diazocarboxylates produced the respective beta-lactones. In general beta-lactone formation was shown to be the only detectable C-H insertion pathway for the latter substrate class irrespective of the ester substituent. The beta-lactone products (eight examples) were obtained in yields of 41-68% with a diastereomeric ratio (dr) of 75:25 to 96:4 in favor of the trans diastereoisomer. The 2-bromo substituent could be displaced by an aryl group in a subsequent Suzuki cross-coupling reaction.

  DOI：

  10.1055/s-0033-1341062