methyl 2-((1R,2R)-2-(methoxycarbonyl)-2-((E)-styryl)cyclopropyl)benzoate | 1345876-75-6

• 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: methyl 2-((1R,2R)-2-(methoxycarbonyl)-2-((E)-styryl)cyclopropyl)benzoate
• CAS: 1345876-75-6
• 化学式: C₂₁H₂₀O₄
• 分子量: 336.387
• InChiKey: ZVMDHGLCWAKHJR-XQKMKWSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-乙烯基-苯甲酸甲酯 、 (E)-methyl 2-diazo-4-phenylbut-3-enoate 在 dirhodium tetrakis((R)-1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate) 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 methyl 2-((1S,2S)-2-(methoxycarbonyl)-2-((E)-styryl)cyclopropyl)benzoate 、 methyl 2-((1R,2R)-2-(methoxycarbonyl)-2-((E)-styryl)cyclopropyl)benzoate
  参考文献：
  名称：

  D₂-Symmetric Dirhodium Catalyst Derived from a 1,2,2-Triarylcyclopropanecarboxylate Ligand: Design, Synthesis and Application

  摘要：

  Dirhodium tetrakis-(R)-(1-(4-bromophenyl)-2,2-diphenylcyclopropanecarboxylate) (Rh-2(R-BTPCP)(4)) was found to be an effective chiral catalyst for enantioselective reactions of aryl- and styryldiazoacetates. Highly enantioselective cyclopropanations, tandem cyclopropanation/Cope rearrangements and a combined C- functionalization/Cope rearrangement were achieved using Rh-2(R-BTPCP)(4) as catalyst. The advantages of Rh-2(R-BTPCP)(4) include its ease of synthesis, its tolerance to the size of the ester group in the styryldiazoacetates, and its compatibility with clichloromethane as solvent. Computational studies suggest that the catalyst adopts a D-2-symmetric arrangement, but when the carbenoid binds to the catalyst, two of the p-bromophenyl groups on the ligands rotate outward to make room for the carbenoid and the approach of the substrate to the carbenoid.

  DOI：

  10.1021/ja2074104