3-[bis(ethoxycarbonyl)methyl]-2-methylcyclopentanone

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-[bis(ethoxycarbonyl)methyl]-2-methylcyclopentanone
• 英文别名: diethyl 2-(2'-methyl-3'-oxocyclopentyl)malonate；Diethyl 2-(2-methyl-3-oxocyclopentyl)propanedioate
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: PEXZQBCQBWYLLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基环戊烯醇酮 、 丙二酸二乙酯 在 [(R,R)-(+)-(Ph(O^(1-))CHCH₂)2NCH₂Ph]3*3Na⁽¹⁺⁾*La⁽³⁺⁾ 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 20.0h， 以86%的产率得到3-[bis(ethoxycarbonyl)methyl]-2-methylcyclopentanone
  参考文献：
  名称：

  Asymmetric Michael addition reactions using a chiral La–Na aminodiolate catalyst

  摘要：

  (R,R)-(+)-2-[Benzyl-(2-hydroxy-2-phenylethyl)amino]-1-phenylethanol 1 is used as a chiral ligand in the synthesis of an optically active lanthanum-sodium amino diol complex LS-1. This heterobimetallic catalyst is quite effective its an asymmetric catalyst for various Michael addition reactions, H-1 NMR Study indicates the co-ordination of enone to the central lanthanum atom in LS-1. The reaction conditions were optimized and the adducts were obtained in high yield with moderate to high enantiomeric excess under extremely mild conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00240-9

文献信息

• Highly Efficient 1,4-Addition of 1,3-Diesters to Conjugated Enones by In/TMSCl
  作者：Phil Ho Lee、Dong Seomoon、Kooyeon Lee、Yunkiu Heo

  DOI：10.1021/jo026600t

  日期：2003.3.1

  Organoindium reagents derived from indium and diethyl bromomalonates were added to a wide range of conjugated enones in a 1,4-fashion in the presence of TMSCl under mild conditions, and corresponding oxo-1,3-diesters were obtained in good to excellent yields.
• Asymmetric Michael addition reactions using a chiral La–Na aminodiolate catalyst
  作者：N Prabagaran、G Sundararajan

  DOI：10.1016/s0957-4166(02)00240-9

  日期：2002.6

  (R,R)-(+)-2-[Benzyl-(2-hydroxy-2-phenylethyl)amino]-1-phenylethanol 1 is used as a chiral ligand in the synthesis of an optically active lanthanum-sodium amino diol complex LS-1. This heterobimetallic catalyst is quite effective its an asymmetric catalyst for various Michael addition reactions, H-1 NMR Study indicates the co-ordination of enone to the central lanthanum atom in LS-1. The reaction conditions were optimized and the adducts were obtained in high yield with moderate to high enantiomeric excess under extremely mild conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.