(+/-)-trans-2,2-difluoro-3-phenylcyclopropanecarbonitrile | 646995-46-2

• 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: (+/-)-trans-2,2-difluoro-3-phenylcyclopropanecarbonitrile
• 英文别名: Cyclopropanecarbonitrile, 2,2-difluoro-3-phenyl-, (1S,3S)-；(1S,3S)-2,2-difluoro-3-phenylcyclopropane-1-carbonitrile
• CAS: 646995-46-2
• 化学式: C₁₀H₇F₂N
• 分子量: 179.169
• InChiKey: HXHQBMLCELLQDQ-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-2,2-difluoro-3-phenylcyclopropanecarbonitrile 在 氯化亚砜 、 potassium phosphate buffer 、 Rhodococcus sp. AJ₂₇₀ cells 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (1R,3S)-2,2-Difluoro-3-phenyl-cyclopropanecarbonyl chloride
  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 生成 (+/-)-trans-2,2-difluoro-3-phenylcyclopropanecarbonitrile
  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

• Nitrile and Amide Biotransformations for Efficient Synthesis of Enantiopure gem-Dihalocyclopropane Derivatives
  作者：Mei-Xiang Wang、Guo-Qiang Feng、Qi-Yu Zheng

  DOI：10.1002/adsc.200303020

  日期：2003.6

  the cells were strongly determined by the nature of the halogen substituent. The synthetic utility of the biocatalytic process was illustrated by an efficient and multi-gram scale biotransformation and synthesis of enantiopure 2,2-dichloro-3-phenylcyclopropanecarboxylic acid and amide in both enantiomeric forms.

  由Rhodococcus sp。催化。在非常温和的条件下，对AJ270微生物细胞，反式-2,2-二卤代-3-苯基环丙烷腈和-酰胺进行对映体选择性水解。细胞中涉及的腈水合酶和酰胺酶的效率和对映选择性都强烈地取决于卤素取代基的性质。生物催化过程的合成效用通过对映体形式的对映纯2，2-二氯-3-苯基环丙烷羧酸和酰胺的高效，数克规模的生物转化和合成得到了说明。
• Biocatalytic Strategy for the Highly Stereoselective Synthesis of Fluorinated Cyclopropanes
  作者：Juan D. Villada、Jadab Majhi、Valentin Lehuédé、Michelle E. Hendricks、Katharina Neufeld、Veronica Tona、Rudi Fasan

  DOI：10.1002/anie.202406779

  日期：2024.8.12

  A first enantioselective method for the cyclopropanation of difluorinated olefins is presented. Using engineered myoglobin-based catalysts in combination with diazoacetonitrile as the carbene precursor, the present method enables the production of different fluorinated cyclopropanes with high yields and high enantioselectivity.

  提出了第一种二氟化烯烃环丙烷化的对映选择性方法。使用工程化的肌红蛋白基催化剂与作为卡宾前体的重氮乙腈相结合，本方法能够以高产率和高对映选择性生产不同的氟化环丙烷。