ethyl 2-ethoxycarbonyl-3-methyl-5-oxopentanoate | 72666-81-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-ethoxycarbonyl-3-methyl-5-oxopentanoate
• 英文别名: diethyl 2-(1-formylpropan-2-yl)malonate；diethyl 2-[(2S)-4-oxobutan-2-yl]propanedioate
• CAS: 72666-81-0
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: GOVWEZNPUNFOSA-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  (S)-2-{[(E)-But-2-en-(E)-ylidene]amino}-3,3-dimethyl-butyric acid tert-butyl ester 、 丙二酸二乙酯 生成 ethyl 2-ethoxycarbonyl-3-methyl-5-oxopentanoate
  参考文献：
  名称：

  通过手性α，β-不饱和醛亚胺的不对称迈克尔反应

  摘要：

  DOI：

  10.1016/s0040-4039(01)83107-5

文献信息

• Base-Base Bifunctional Catalysis: A Practical Strategy for Asymmetric Michael Addition of Malonates to α,β-Unsaturated Aldehydes
  作者：Yongcan Wang、Pengfei Li、Xinmiao Liang、Jinxing Ye

  DOI：10.1002/adsc.200800070

  日期：2008.6.9

  Lewis base–Brønsted base bifunctional catalysis is a novel and practical strategy for the asymmetric Michael addition. The addition of malonates to a series of α,β-unsaturated aldehydes can take place under base–base bifunctional catalytic conditions using 0.5–5 mol% of (S)-2-[diphenyl(trimethylsilyloxy)methyl]pyrrolidine as catalyst and 5–30 mol% of lithium 4-fluorobenzoate as additive base with up

  刘易斯碱-布朗斯台德碱双功能催化是不对称迈克尔加成的一种新颖而实用的策略。丙二酸酯在一系列α，β-不饱和醛中的添加可以在碱-碱双功能催化条件下进行，使用0.5-5 mol％的（S）-2- [二苯基（三甲基甲硅烷氧基）甲基]吡咯烷和5- 30 mol％的4-氟苯甲酸锂作为添加剂碱，ee最高可达99％。
• ——
  作者：K. A. Kochetkov、S. R. Harutyunyan、N. A. Kuz"mina、T. F. Savel"eva、V. I. Maleev、A. S. Peregudov、S. Vyskočil、A. S. Sagiyan

  DOI：10.1023/a:1013090619703

  日期：——

  Alkali metal salts of substituted (S)-prolines, alkali metal alkoxides of (S)-prolinol, and Na salts of chiral substituted 2-amino-2'-hydroxy-1,1'-binaphthyls can catalyze the asymmetric Michael reaction of diethyl malonate with crotonaldehyde to give adducts in >90% yields with ee up to 40%. The influences of the catalyst structure, the nature of the alkali metal cation, temperature, the solvent, and salt additives on the reaction outcome were studied.