2-(RS)-[2-(dimethylamino)-2-oxoethyl]-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester | 253593-04-3

• 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: 2-(RS)-[2-(dimethylamino)-2-oxoethyl]-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester
• CAS: 253593-04-3
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: PRGLGWVPMPTYMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(RS)-[2-(dimethylamino)-2-oxoethyl]-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester 在 sodium hydroxide 、 Alcalase 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 (R)-2-Dimethylcarbamoylmethyl-succinic acid 4-tert-butyl ester 、 (S)-2-Dimethylcarbamoylmethyl-succinic acid 4-tert-butyl ester
  参考文献：
  名称：

  Chemo-enzymatic synthesis of chiral 2-substituted succinic acid derivatives

  摘要：

  Prochiral discrimination by the biocatalyst Alcalase(R), an enzyme preparation of subtilisin Carlsberg, was used to effect enantio- and regioselective monohydrolysis of a variety of(RS)-2-substituted succinate diesters to afford the corresponding half esters in modest to excellent enantiomeric excesses (>99%). Exploitation of malonate chemistry, as well as recycling of the unhydrolyzed isomer from the enantioselective hydrolysis, has resulted in a process which is both practical and economical. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00330-4
• 作为产物：
  描述：

  dimethyl (N,N-dimethylcarbamoylmethyl)malonate 在 sodium hexamethyldisilazane 、 lithium bromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-(RS)-[2-(dimethylamino)-2-oxoethyl]-1,4-butanedioic acid 4-(1,1-dimethylethyl) 1-methyl ester
  参考文献：
  名称：

  Chemo-enzymatic synthesis of chiral 2-substituted succinic acid derivatives

  摘要：

  Prochiral discrimination by the biocatalyst Alcalase(R), an enzyme preparation of subtilisin Carlsberg, was used to effect enantio- and regioselective monohydrolysis of a variety of(RS)-2-substituted succinate diesters to afford the corresponding half esters in modest to excellent enantiomeric excesses (>99%). Exploitation of malonate chemistry, as well as recycling of the unhydrolyzed isomer from the enantioselective hydrolysis, has resulted in a process which is both practical and economical. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00330-4