(1R)-2,2-dimethylcyclopropane-1-(2,2,2-trifluoroethoxycarbonyl)-1-carboxylic acid | 345978-25-8

• 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: (1R)-2,2-dimethylcyclopropane-1-(2,2,2-trifluoroethoxycarbonyl)-1-carboxylic acid
• 英文别名: (1R)-2,2-dimethyl-1-(2,2,2-trifluoroethoxycarbonyl)cyclopropane-1-carboxylic acid
• CAS: 345978-25-8
• 化学式: C₉H₁₁F₃O₄
• 分子量: 240.179
• InChiKey: FTWIKOODWQLARW-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙醇 、 (1R)-2,2-dimethylcyclopropane-1-(2,2,2-trifluoroethoxycarbonyl)-1-carboxylic acid 在 二苯基磷酸 、 三乙胺 作用下， 以 甲苯 、 乙酸乙酯 为溶剂， 反应 18.0h， 以34%的产率得到(1S)-2,2,2-trifluoroethyl 2,2-dimethylcyclopropane-1-(N-ethoxycarbonylamino)-1-carboxylate
  参考文献：
  名称：

  Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate

  摘要：

  Hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate with pig liver esterase afforded (1R)-2,2-dimethyl-1-(2,2,2-trifluoroethoxycarbonyl)-cyclopropane-1-carboxylic acid in high enantiomeric excess. This compound was rearranged to (1S)-2,2,2-trifluoroethyl-2,2-dimethyl-1-[(N-ethoxycarbonyl)amino]-cyclopropane-1-carboxylate via a Curtius type reaction with DPPA. Final alkaline hydrolysis gave (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00112-0
• 作为产物：
  描述：

  dimethyl 2,2-dimethyl-cyclopropane-1,1-dicarboxylate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 phosphate buffer 、 二氯甲烷 为溶剂， 反应 190.0h， 生成 (1R)-2,2-dimethylcyclopropane-1-(2,2,2-trifluoroethoxycarbonyl)-1-carboxylic acid
  参考文献：
  名称：

  Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate

  摘要：

  Hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate with pig liver esterase afforded (1R)-2,2-dimethyl-1-(2,2,2-trifluoroethoxycarbonyl)-cyclopropane-1-carboxylic acid in high enantiomeric excess. This compound was rearranged to (1S)-2,2,2-trifluoroethyl-2,2-dimethyl-1-[(N-ethoxycarbonyl)amino]-cyclopropane-1-carboxylate via a Curtius type reaction with DPPA. Final alkaline hydrolysis gave (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00112-0

文献信息

• Synthesis of (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid via PLE mediated hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate
  作者：Antonio Salgado、Tom Huybrechts、Annelies Eeckhaut、Johan Van der Eycken、Zsolt Szakonyi、Ferenc Fülöp、Alexey Tkachev、Norbert De Kimpe

  DOI：10.1016/s0040-4020(01)00112-0

  日期：2001.4

  Hydrolysis of bis(2,2,2-trifluoroethyl) 2,2-dimethylcyclopropane-1,1-dicarboxylate with pig liver esterase afforded (1R)-2,2-dimethyl-1-(2,2,2-trifluoroethoxycarbonyl)-cyclopropane-1-carboxylic acid in high enantiomeric excess. This compound was rearranged to (1S)-2,2,2-trifluoroethyl-2,2-dimethyl-1-[(N-ethoxycarbonyl)amino]-cyclopropane-1-carboxylate via a Curtius type reaction with DPPA. Final alkaline hydrolysis gave (1S)-1-amino-2,2-dimethylcyclopropane-1-carboxylic acid. (C) 2001 Elsevier Science Ltd. All rights reserved.