tert-butyl 2-acetyl-2-methyl-cyclopropanecarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: tert-butyl 2-acetyl-2-methyl-cyclopropanecarboxylate
• 英文别名: Tert-butyl 2-acetyl-2-methylcyclopropane-1-carboxylate
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: ZSLGMYUTXIEHOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-1-丁烯-3-酮 、 重氮基乙酸叔丁酯 在 4-二甲氨基吡啶 作用下， 以 氯苯 为溶剂， 反应 20.0h， 生成 tert-butyl 2-acetyl-2-methyl-cyclopropanecarboxylate 、 tert-butyl 2-acetyl-2-methyl-cyclopropanecarboxylate 、 tert-butyl 2-acetyl-2-methyl-cyclopropanecarboxylate
  参考文献：
  名称：

  Cobalt-Catalyzed Asymmetric Cyclopropanation of Electron-Deficient Olefins

  摘要：

  The cobalt(II) complex of a D 2-Symmetric chiral porphyrin [Co(1)] is an effective catalyst for asymmetric cyclopropanation of electron-deficient olefins, including M,P-unsaturated esters, amides, ketones, and nitriles. Due to the absence of dimerization of diazo compounds, the catalytic reactions can be performed in one-pot protocol using olefins as the limiting reagent, forming the desired electrophilic cyclopropane derivatives in high yields and selectivities under mild conditions. In most cases, both excellent diastereo- and enantioselectivity were achieved.

  DOI：

  10.1021/ja074613o

文献信息

• ASYMMETRIC CYCLOPROPANATION OF ELECTRON-DEFICIENT OLEFINS WITH DIAZO REAGENTS
  申请人：Zhang X. Peter

  公开号：US20100076239A1

  公开（公告）日：2010-03-25

  Cobalt-catalyzed asymmetric cyclopropanation of electron-deficient olefins.

  钴催化的电子不足烯烃不对称环丙烷化。
• COBALT-CATALYZED ASYMMETRIC CYCLOPROPANATION OF ELECTRON-DEFICIENT OLEFINS
  申请人：Zhang X. Peter

  公开号：US20090069519A1

  公开（公告）日：2009-03-12

  Cobalt-catalyzed asymmetric cyclopropanation of electron-deficient olefins.
• US7847041B2
  申请人：——

  公开号：US7847041B2

  公开（公告）日：2010-12-07
• Cobalt-Catalyzed Asymmetric Cyclopropanation of Electron-Deficient Olefins
  作者：Ying Chen、Joshua V. Ruppel、X. Peter Zhang

  DOI：10.1021/ja074613o

  日期：2007.10.1

  The cobalt(II) complex of a D 2-Symmetric chiral porphyrin [Co(1)] is an effective catalyst for asymmetric cyclopropanation of electron-deficient olefins, including M,P-unsaturated esters, amides, ketones, and nitriles. Due to the absence of dimerization of diazo compounds, the catalytic reactions can be performed in one-pot protocol using olefins as the limiting reagent, forming the desired electrophilic cyclopropane derivatives in high yields and selectivities under mild conditions. In most cases, both excellent diastereo- and enantioselectivity were achieved.