(+)-(1S,3S)-2,2-difluoro-3-phenylcyclopropanecarboxylic acid | 646995-45-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(1S,3S)-2,2-difluoro-3-phenylcyclopropanecarboxylic acid
• 英文别名: Cyclopropanecarboxylic acid, 2,2-difluoro-3-phenyl-, (1S,3S)-；(1S,3S)-2,2-difluoro-3-phenylcyclopropane-1-carboxylic acid
• CAS: 646995-45-1
• 化学式: C₁₀H₈F₂O₂
• 分子量: 198.169
• InChiKey: ZJTJSILEHUGFMC-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(1S,3S)-2,2-difluoro-3-phenylcyclopropanecarboxylic acid 在 ammonium hydroxide 、 氯化亚砜 作用下， 以 乙酸乙酯 为溶剂， 生成 (+)-(1S,3S)-2,2-difluoro-3-phenylcyclopropanecarboxamide
  参考文献：
  名称：

  Synthesis of high enantiomeric purity gem-dihalocyclopropane derivatives from biotransformations of nitriles and amides

  摘要：

  Enantioselective biotransformations of geminally dihalogenated cyclopropanecarbonitriles and amides are described. Both the reaction rate and enantioselectivity of the nitrile hydratase and amidase involved in Rhodococcus sp. AJ270 microbial cells are strongly governed by the nature of gein-disubstituents on the cyclopropane ring; the amidase generally exhibits steric dependence on the substituents while both the steric and electronic factors of the substituents may affect the action of the nitrile hydratase. The match of steric bulkiness of the substituents at 2- with that at 3-positions on the cyclopropane ring benefits the efficient and highly enantioselective reaction. Coupled with facile chemical transformations, biocatalytic transformations of nitrile and amide supply an effective synthesis of optically active 2,2-disubstitued-3-phenylcyclopropanecarboxylic acid and amide in both enantiomeric forms. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.016
• 作为产物：
  描述：

  trans-(+/-)-2,2-difluoro-3-phenylcyclopropane-1-carboxylic acid 在 potassium phosphate buffer 、 Rhodococcus sp. AJ₂₇₀ cells 作用下， 反应 0.25h， 生成 (+)-(1S,3S)-2,2-difluoro-3-phenylcyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis of high enantiomeric purity gem-dihalocyclopropane derivatives from biotransformations of nitriles and amides

  摘要：

  Enantioselective biotransformations of geminally dihalogenated cyclopropanecarbonitriles and amides are described. Both the reaction rate and enantioselectivity of the nitrile hydratase and amidase involved in Rhodococcus sp. AJ270 microbial cells are strongly governed by the nature of gein-disubstituents on the cyclopropane ring; the amidase generally exhibits steric dependence on the substituents while both the steric and electronic factors of the substituents may affect the action of the nitrile hydratase. The match of steric bulkiness of the substituents at 2- with that at 3-positions on the cyclopropane ring benefits the efficient and highly enantioselective reaction. Coupled with facile chemical transformations, biocatalytic transformations of nitrile and amide supply an effective synthesis of optically active 2,2-disubstitued-3-phenylcyclopropanecarboxylic acid and amide in both enantiomeric forms. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.11.016

文献信息

• Biocatalytic Enantioselective Reduction of Cyclopropenyl Esters and Ketones Using Ene-Reductases
  作者：Tomohiro Yasukawa、Pierre Gilles、Juliette Martin、Julien Boutet、Janine Cossy

  DOI：10.1021/acscatal.4c00899

  日期：2024.4.19

  Enantioselective reduction of cyclopropenyl esters and ketones to optically active cyclopropanes has been achieved by using whole-cell-overexpressing ene-reductases (EREDs). By using these enzymes, trans-cyclopropanes were isolated in good yield and high enantiomeric excess. A wide range of optically active cyclopropane esters and ketones were obtained, and a variety of substituent patterns on the

  通过使用全细胞过表达烯还原酶（ERED），可以将环丙烯酯和酮对映选择性还原为光学活性环丙烷。通过使用这些酶，以良好的产率和高对映体过量分离反式环丙烷。获得了多种光学活性环丙烷酯和酮，并且环丙烯上可以容忍多种取代基模式。
• Synthesis of high enantiomeric purity gem-dihalocyclopropane derivatives from biotransformations of nitriles and amides
  作者：Mei-Xiang Wang、Guo-Qiang Feng、Qi-Yu Zheng

  DOI：10.1016/j.tetasy.2003.11.016

  日期：2004.1

  Enantioselective biotransformations of geminally dihalogenated cyclopropanecarbonitriles and amides are described. Both the reaction rate and enantioselectivity of the nitrile hydratase and amidase involved in Rhodococcus sp. AJ270 microbial cells are strongly governed by the nature of gein-disubstituents on the cyclopropane ring; the amidase generally exhibits steric dependence on the substituents while both the steric and electronic factors of the substituents may affect the action of the nitrile hydratase. The match of steric bulkiness of the substituents at 2- with that at 3-positions on the cyclopropane ring benefits the efficient and highly enantioselective reaction. Coupled with facile chemical transformations, biocatalytic transformations of nitrile and amide supply an effective synthesis of optically active 2,2-disubstitued-3-phenylcyclopropanecarboxylic acid and amide in both enantiomeric forms. (C) 2003 Elsevier Ltd. All rights reserved.