丙基(1S,2S)-2-氟环丙烷羧酸酯 | 177564-59-9

• 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
• 中文名称: 丙基(1S,2S)-2-氟环丙烷羧酸酯
• 中文别名: 苯丙酸,b-氨基-2-硝基-,(bS)-
• 英文名称: Propyl (1S,2S)-2-fluorocyclopropane-1-carboxylate
• CAS: 177564-59-9
• 化学式: C₇H₁₁FO₂
• 分子量: 146.162
• InChiKey: IKWJPUDPGPUZQK-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙基(1S,2S)-2-氟环丙烷羧酸酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (1S,2S)-2-氟环丙烷羧酸
  参考文献：
  名称：

  Resolution of cis-2-fluorocyclopropanecarboxylic acid by a microbial enantioselective hydrolysis

  摘要：

  The important key intermediate of quinolone analogue synthesis, (1S,2S)-2-fluorocyclopropanecarboxylic acid, was prepared enantioselectively by a microbial resolution. One of the strains with the highest enzymatic specificity was selected from soil and when lyophilized cells were treated with corresponding ester, the remaining (IS,2S)-ester was obtained with high enantiomeric purity (98% e.e.). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00321-8
• 作为产物：
  描述：

  Propyl (1R,2R)-2-fluorocyclopropane-1-carboxylate 生成 丙基(1S,2S)-2-氟环丙烷羧酸酯
  参考文献：
  名称：

  Resolution of cis-2-fluorocyclopropanecarboxylic acid by a microbial enantioselective hydrolysis

  摘要：

  The important key intermediate of quinolone analogue synthesis, (1S,2S)-2-fluorocyclopropanecarboxylic acid, was prepared enantioselectively by a microbial resolution. One of the strains with the highest enzymatic specificity was selected from soil and when lyophilized cells were treated with corresponding ester, the remaining (IS,2S)-ester was obtained with high enantiomeric purity (98% e.e.). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00321-8

文献信息

• Purification, Properties and Reactivity of the Esterase from Micrococcu sp.
  作者：Akihiro IMURA、Motohiro ITOH、Akihiko MIYADERA

  DOI：10.1248/bpb.22.654

  日期：——

  The esterase form Micrococcus sp., which hydrolyzes n-propyl-2-fluorocyclopropanecarboxylate (3) enantioselectively, was highly purified by three types of chromatography. The purified enzyme was inactivated by Hg and diisopropyl fluorophosphate (DFP). It was a monomer with a molecular weight of about 35000. The enzyme exhibits esterase activity towards many aliphatic propyl esters. The enantioselectivity for substrate (3) using purified enzyme did not differ from that of crude enzyme.

  微球菌（Micrococcus sp.）的酯酶能对映选择性地水解正丙基-2-氟环丙烷羧酸酯（3）。纯化的酶被汞和氟磷酸二异丙酯（DFP）灭活。它是一种分子量约为 35000 的单体。该酶对许多脂肪族丙基酯具有酯酶活性。纯化酶对底物（3）的对映选择性与粗酶没有差别。