(1R,3R)-3-((Z)-2-Chloro-3,3,3-trifluoro-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid (S)-cyano-(4-fluoro-3-phenoxy-phenyl)-methyl ester | 102281-48-1

• 分子结构分类: 有机化合物
• 英文名称: (1R,3R)-3-((Z)-2-Chloro-3,3,3-trifluoro-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid (S)-cyano-(4-fluoro-3-phenoxy-phenyl)-methyl ester
• 英文别名: Cyclopropanecarboxylic acid, 3-((1Z)-2-chloro-3,3,3-trifluoro-1-propen-1-yl)-2,2-dimethyl-, (S)-cyano(4-fluoro-3-phenoxyphenyl)methyl ester, (1R,3R)-；[(S)-cyano-(4-fluoro-3-phenoxyphenyl)methyl] (1R,3R)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 102281-48-1
• 化学式: C₂₃H₁₈ClF₄NO₃
• 分子量: 467.847
• InChiKey: LZYWAWOQVVKRKF-SJPGYQGTSA-N

物化性质

• 沸点：
  484.7±45.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,3R)-3-((Z)-2-Chloro-3,3,3-trifluoro-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid (S)-cyano-(4-fluoro-3-phenoxy-phenyl)-methyl ester 在 Selectfluor 作用下， 以 乙腈 为溶剂， 150.0 ℃ 、1.62 MPa 条件下， 反应 0.33h， 以14%的产率得到α-cyano-4-fluoro-3-(2-fluorophenoxy)-benzyl (Z)-(1R,3R)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate
  参考文献：
  名称：

  Microwave fluorination: a novel, rapid approach to fluorination with Selectfluor®

  摘要：

  Fluorination of electron rich aromatic systems with electrophilic fluorination reagents such as Selectfluor(R) and Accufluor(R) is a well-established process. Herein we report results from investigations into the use of such procedures to perform rapid, small-scale fluorinations under microwave irradiation. We have investigated the transformation with a ranee of different substrates and discuss the effects of two key factors, namely reaction time and choice of fluorination reagent. The use of Selectfluor(R) in acetonitrile at 150 degreesC with microwave heating for 10 min affords products in comparable yields to those obtained by prolonged heating in acetonitrile at its reflux temperature. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.06.015