(S,S)-2-acetyl-4-acetylamino-2-methyl-pentanedioic acid dimethyl ester | 691384-81-3

• 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: (S,S)-2-acetyl-4-acetylamino-2-methyl-pentanedioic acid dimethyl ester
• 英文别名: dimethyl (2S,4S)-4-acetamido-2-acetyl-2-methylpentanedioate
• CAS: 691384-81-3
• 化学式: C₁₂H₁₉NO₆
• 分子量: 273.286
• InChiKey: ZFTUMNCYWGTNLD-CABZTGNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  98.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S,S)-2-acetyl-4-acetylamino-2-methyl-pentanedioic acid dimethyl ester 在 氨 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以90%的产率得到(S,S)-4-acetyl-4-methyl-5-oxo-pyrrolidine-2-carboxylic acid amide
  参考文献：
  名称：

  Asymmetric Michael reaction between a chiral α,β-dimethyl-β-enamino ester and α-substituted acrylates

  摘要：

  An asymmetric Michael reaction between a chiral alpha,beta-dimethyl-beta-enamino ester derived from (S)-1-phenylethylamine and alpha-substituted acrylates is reported. Methyl acetamidoacrylate and methyl acetoxyacrylate furnished the expected Michael adduct with good ee's and de's. By contrast, an annulation process of the intermediary imine took place when using methyl methacrylates. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.028
• 作为产物：
  描述：

  (2Z)-(+)-methyl 2-methyl-3-[(S)-α-methylbenzylamino]-2-butenoate 在 溶剂黄146 、 对苯二酚 作用下， 以 四氢呋喃 为溶剂， 反应 74.0h， 生成 (S,S)-2-acetyl-4-acetylamino-2-methyl-pentanedioic acid dimethyl ester
  参考文献：
  名称：

  Asymmetric Michael reaction between a chiral α,β-dimethyl-β-enamino ester and α-substituted acrylates

  摘要：

  An asymmetric Michael reaction between a chiral alpha,beta-dimethyl-beta-enamino ester derived from (S)-1-phenylethylamine and alpha-substituted acrylates is reported. Methyl acetamidoacrylate and methyl acetoxyacrylate furnished the expected Michael adduct with good ee's and de's. By contrast, an annulation process of the intermediary imine took place when using methyl methacrylates. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.028

文献信息

• Asymmetric synthesis of glutamate derivatives
  作者：Rokhayatou Seck、Abdoulaye Gassama、Mohammed Nour、Luc Demange、Christian Cavé

  DOI：10.24820/ark.5550190.p009.974

  日期：——
• Asymmetric Michael reaction between a chiral α,β-dimethyl-β-enamino ester and α-substituted acrylates
  作者：Frédéric Hendra、Mohammed Nour、Isabelle Baglin、Georges Morgant、Christian Cavé

  DOI：10.1016/j.tetasy.2004.01.028

  日期：2004.3

  An asymmetric Michael reaction between a chiral alpha,beta-dimethyl-beta-enamino ester derived from (S)-1-phenylethylamine and alpha-substituted acrylates is reported. Methyl acetamidoacrylate and methyl acetoxyacrylate furnished the expected Michael adduct with good ee's and de's. By contrast, an annulation process of the intermediary imine took place when using methyl methacrylates. (C) 2004 Elsevier Ltd. All rights reserved.