(1R,2R,3S,1'R) 2-(1-hydroxyethyl)-3-(1-methylethyl)-cyclopropyl-1-methylethyl ketone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3S,1'R) 2-(1-hydroxyethyl)-3-(1-methylethyl)-cyclopropyl-1-methylethyl ketone
• 英文别名: 1-[(1R,2R,3S)-2-[(1R)-1-hydroxyethyl]-3-propan-2-ylcyclopropyl]-2-methylpropan-1-one
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: GVHBFWXXZHUGHW-LMLFDSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (2E,4E)-1-methylethyl-2,4-hexadien-1-one 在 间氯过氧苯甲酸 、 zinc dibromide 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 16.08h， 生成 (1R,2R,3S,1'R) 2-(1-hydroxyethyl)-3-(1-methylethyl)-cyclopropyl-1-methylethyl ketone
  参考文献：
  名称：

  Regio- and Stereocontrol in the Michael-Initiated Ring-Closure Reactions of γ,δ-Epoxy-α,β-unsaturated Esters, Ketones, Sulfones, and Amides

  摘要：

  Organozincates or Grignard reagents in the presence of zinc catalysts undergo Michael initiated ring closure (MIRC) reactions with gamma,delta-epoxy-alpha,beta-enoates, enones, enesulfones, and enamides to afford 1,2,3-trisubstituted cyclopropanes. The direction of diastereoselectivity is solvent dependent for alkyl Grignard reagents reacting with epoxy enoates, ensulfones, and enamides but solvent independent for the enones. Excellent diastereoselectivity can be achieved for the epoxy enoates, enones, and ensulfones, while the enamides afford modest diastereoselectivity under optimal conditions. The MIRC reaction can be achieved with phenylmagnesium chloride and these substrates under reaction conditions designed to minimize biphenyl formation.

  DOI：

  10.1021/jo402075d

文献信息

• Regio- and Stereocontrol in the Michael-Initiated Ring-Closure Reactions of γ,δ-Epoxy-α,β-unsaturated Esters, Ketones, Sulfones, and Amides
  作者：Ramesh C. Dhakal、R. Karl Dieter

  DOI：10.1021/jo402075d

  日期：2013.12.20

  Organozincates or Grignard reagents in the presence of zinc catalysts undergo Michael initiated ring closure (MIRC) reactions with gamma,delta-epoxy-alpha,beta-enoates, enones, enesulfones, and enamides to afford 1,2,3-trisubstituted cyclopropanes. The direction of diastereoselectivity is solvent dependent for alkyl Grignard reagents reacting with epoxy enoates, ensulfones, and enamides but solvent independent for the enones. Excellent diastereoselectivity can be achieved for the epoxy enoates, enones, and ensulfones, while the enamides afford modest diastereoselectivity under optimal conditions. The MIRC reaction can be achieved with phenylmagnesium chloride and these substrates under reaction conditions designed to minimize biphenyl formation.