methyl 2-(2-(4-bromobenzoyl)-3-phenylcyclopropyl)-2-oxoacetate | 1260497-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-(2-(4-bromobenzoyl)-3-phenylcyclopropyl)-2-oxoacetate
• 英文别名: methyl 2-[(1S,2R,3R)-2-(4-bromobenzoyl)-3-phenylcyclopropyl]-2-oxoacetate
• CAS: 1260497-92-4
• 化学式: C₁₉H₁₅BrO₄
• 分子量: 387.23
• InChiKey: WUXNUUIDIYMDHB-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 4-phenyl-2-oxo-3-butenoate 、 1-(4-bromophenyl)-2-(dimethyl-λ4-sulfanylidene)ethanone 在 1,1'-((1R,2R)-1,2-diphenylethane-1,2-diyl)bis(3-(3,5-bis(trifluoromethyl)phenyl)urea) 作用下， 以 甲苯 为溶剂， 反应 72.5h， 生成 methyl 2-(2-(4-bromobenzoyl)-3-phenylcyclopropyl)-2-oxoacetate 、 methyl 2-(2-(4-bromobenzoyl)-3-phenylcyclopropyl)-2-oxoacetate 、 methyl 2-(2-(4-bromobenzoyl)-3-phenylcyclopropyl)-2-oxoacetate
  参考文献：
  名称：

  Asymmetric Cyclopropanation of β,γ-Unsaturated α-Ketoesters with Stabilized Sulfur Ylides Catalyzed by C₂-Symmetric Ureas

  摘要：

  A novel organocatalytic asymmetric cyclopropanation of beta,gamma-unsaturated alpha-ketoesters with stabilized sulfur ylides using C-2-symmetric urea as a hydrogen-bond catalyst has been described. This reaction allows an efficient access to 1,2,3-trisubstituted cyclopropane derivatives in moderate to good yields with up to 16:1 dr and 90: I 0 er under mild reaction conditions. The mechanism study proved that the high stereoinduction originated from the cooperative effect of the hydrogen-bond catalyst.

  DOI：

  10.1021/jo101699r

文献信息

• Asymmetric Cyclopropanation of β,γ-Unsaturated α-Ketoesters with Stabilized Sulfur Ylides Catalyzed by <i>C</i>₂-Symmetric Ureas
  作者：Ying Cheng、Jing An、Liang-Qiu Lu、Lan Luo、Zheng-Yi Wang、Jia-Rong Chen、Wen-Jing Xiao

  DOI：10.1021/jo101699r

  日期：2011.1.7

  A novel organocatalytic asymmetric cyclopropanation of beta,gamma-unsaturated alpha-ketoesters with stabilized sulfur ylides using C-2-symmetric urea as a hydrogen-bond catalyst has been described. This reaction allows an efficient access to 1,2,3-trisubstituted cyclopropane derivatives in moderate to good yields with up to 16:1 dr and 90: I 0 er under mild reaction conditions. The mechanism study proved that the high stereoinduction originated from the cooperative effect of the hydrogen-bond catalyst.