methyl (1S,2E)-1-(4-bromophenyl)-2-(1-trimethylsilylethylidene)cyclopropane-1-carboxylate | 1187852-66-9

• 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 (1S,2E)-1-(4-bromophenyl)-2-(1-trimethylsilylethylidene)cyclopropane-1-carboxylate
• CAS: 1187852-66-9
• 化学式: C₁₆H₂₁BrO₂Si
• 分子量: 353.331
• InChiKey: XHWUQQBIGNNYDP-UKYUDJEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-甲基-1-三甲基甲硅烷基丙二烯 、 methyl 2-(4-bromophenyl)-2-diazoacetate 在 Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 作用下， 以 正己烷 为溶剂， 生成 、 methyl (1S,2E)-1-(4-bromophenyl)-2-(1-trimethylsilylethylidene)cyclopropane-1-carboxylate
  参考文献：
  名称：

  Rhodium-Mediated Enantioselective Cyclopropanation of Allenes

  摘要：

  Reaction of monosubstituted allenes with aryldiazoacetate esters under dirhodium tetracarboxylate catalysis led to alkylidene cyclopropane products in 80-90% ee. Monosubstituted alkyl- and arylallene substrates gave 60-75% yield under standard conditions, while yields for 1,1-disubstituted allenes were significantly lower. Cyclopropanation of 1-methyl-1-(trimethylsilyl)allene proceeded in higher yield than other 1,1-disubstituted substrates, suggesting rate enhancement mediated by a significant beta-silicon effect.

  DOI：

  10.1021/ol9017968

文献信息

• Rhodium-Mediated Enantioselective Cyclopropanation of Allenes
  作者：Timothy M. Gregg、Mark K. Farrugia、John R. Frost

  DOI：10.1021/ol9017968

  日期：2009.10.1

  Reaction of monosubstituted allenes with aryldiazoacetate esters under dirhodium tetracarboxylate catalysis led to alkylidene cyclopropane products in 80-90% ee. Monosubstituted alkyl- and arylallene substrates gave 60-75% yield under standard conditions, while yields for 1,1-disubstituted allenes were significantly lower. Cyclopropanation of 1-methyl-1-(trimethylsilyl)allene proceeded in higher yield than other 1,1-disubstituted substrates, suggesting rate enhancement mediated by a significant beta-silicon effect.