methyl 2-oxo-2-(2-phenyl-3-(thiophene-2-carbonyl)cyclopropyl)acetate | 1260497-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-oxo-2-(2-phenyl-3-(thiophene-2-carbonyl)cyclopropyl)acetate
• 英文别名: methyl 2-oxo-2-[(1S,2S,3R)-2-phenyl-3-(thiophene-2-carbonyl)cyclopropyl]acetate
• CAS: 1260497-95-7
• 化学式: C₁₇H₁₄O₄S
• 分子量: 314.362
• InChiKey: JGUDVRMJWHPSHB-MCIONIFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 4-phenyl-2-oxo-3-butenoate 、 2-(dimethyl-λ4-sulfaneylidene)-1-(thiophen-2-yl)ethan-1-one 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-oxo-2-(2-phenyl-3-(thiophene-2-carbonyl)cyclopropyl)acetate 、 methyl 2-oxo-2-((1R,2R,3S)-2-phenyl-3-(thiophene-2-carbonyl)cyclopropyl)acetate 、 methyl 2-oxo-2-(2-phenyl-3-(thiophene-2-carbonyl)cyclopropyl)acetate
  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.