(1S,2R,3S)-methyl 1-(4-bromophenyl)-2-(4-methoxyphenyl)-3-methylcyclopropanecarboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2R,3S)-methyl 1-(4-bromophenyl)-2-(4-methoxyphenyl)-3-methylcyclopropanecarboxylate
• 英文别名: methyl (1S,2R,3S)-1-(4-bromophenyl)-2-(4-methoxyphenyl)-3-methylcyclopropane-1-carboxylate
• 化学式: C₁₉H₁₉BrO₃
• 分子量: 375.262
• InChiKey: YEQLYMORTZENGI-OEPMTFCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  茴香烯 、 methyl 2-(4-bromophenyl)-2-diazoacetate 在 Rh₂(esp)2 作用下， 以 various solvent(s) 为溶剂， 反应 5.0h， 以74%的产率得到(1S,2R,3S)-methyl 1-(4-bromophenyl)-2-(4-methoxyphenyl)-3-methylcyclopropanecarboxylate
  参考文献：
  名称：

  Balance between Allylic C−H Activation and Cyclopropanation in the Reactions of Donor/Acceptor-Substituted Rhodium Carbenoids with trans-Alkenes

  摘要：

  Rhodium(II)-catalyzed reactions of aryldiazoacetates with (E)-aryl-substituted alkenes generate C-H insertion products and/or cyclopropanes. The product distribution is influenced by the nature of the donor group on the carbenold, the structure of the (E)-aryl-substituted alkenes, and the rhodium catalyst.

  DOI：

  10.1021/ol702218w

文献信息

• Role of Sterically Demanding Chiral Dirhodium Catalysts in Site-Selective C–H Functionalization of Activated Primary C–H Bonds
  作者：Changming Qin、Huw M. L. Davies

  DOI：10.1021/ja504797x

  日期：2014.7.9

  sterically demanding dirhodium tetracarboxylate catalysts on the site selectivity of C-H functionalization by means of rhodium carbene-induced C-H insertion is described. The established dirhodium tetraprolinate-catalyzed reactions of aryldiazoacetates cause preferential C-H functionalization of secondary C-H bonds as a result of competing steric and electronic effects. The sterically more demanding dirhodium

  描述了空间要求严格的四羧酸二铑催化剂通过铑卡宾诱导的 CH 插入对 CH 官能化的位点选择性的影响。由于竞争性空间和电子效应，已建立的四脯氨酸二铑催化芳基重氮乙酸酯反应导致二级 CH 键的优先 CH 官能化。空间上要求更高的四（三芳基环丙烷羧酸）二铑催化剂，例如四[（R）-（1-（联苯）-2,2-二苯基环丙烷羧酸）] [Rh2（R-BPCP）4]，有利于活化伯的 CH 官能化CH 债券。使用该催化剂实现了对包含伯苄基、烯丙基和甲氧基 CH 键的各种简单底物的高度位点选择性和对映选择性 CH 官能化。
• Balance between Allylic C−H Activation and Cyclopropanation in the Reactions of Donor/Acceptor-Substituted Rhodium Carbenoids with <i>trans</i>-Alkenes
  作者：Huw M. L. Davies、Michael G. Coleman、Dominic L. Ventura

  DOI：10.1021/ol702218w

  日期：2007.11.1

  Rhodium(II)-catalyzed reactions of aryldiazoacetates with (E)-aryl-substituted alkenes generate C-H insertion products and/or cyclopropanes. The product distribution is influenced by the nature of the donor group on the carbenold, the structure of the (E)-aryl-substituted alkenes, and the rhodium catalyst.