3-chloro-2,2,3-trifluoro-propionic acid amide | 425-96-7

• 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: 3-chloro-2,2,3-trifluoro-propionic acid amide
• 英文别名: 3-Chlor-2,2,3-trifluor-propionsaeure-amid；3-Chloro-2,2,3-trifluoropropanamide
• CAS: 425-96-7
• 化学式: C₃H₃ClF₃NO
• 分子量: 161.511
• InChiKey: YAFMUUGDSPXVJO-UHFFFAOYSA-N

物化性质

• 沸点：
  198-200 °C
• 密度：
  1.509±0.06 g/cm3(Predicted)
• 熔点：
  41-42 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-2,2,3-trifluoro-propionic acid amide 在 phosphorus pentoxide 作用下， 生成 3-chloro-2,2,3-trifluoropropionitrile
  参考文献：
  名称：

  Halogenated Diazirines as Photolabel Mimics of the Inhaled Haloalkane Anesthetics

  摘要：

  The inhaled anesthetics are low affinity volatile compounds whose mechanism of action remains unclear, in part due to the difficulty of determining their binding targets. Photolabeling may help resolve this difficulty, and thus we have synthesized six compounds (four previously unreported) with structural and physical similarity to halothane (1-bromo-1-chloro-2,2,2-trifluoroethane), a commonly used clinical anesthetic. These compounds incorporate either a diazo, diazirine, or azido group to provide photolability in the long-UV range and to provide a highly reactive photolysis product. While several of the compounds have immobilizing activity in tadpoles, it is complicated by either toxicity or very low potency. One compound however, a halogenated three-carbon diazirine 4, is a potent anesthetic, is apparently nontoxic, potentiates GABA(A) Cl- currents, and stabilizes serum albumin, all of which are features of halothane. When tagged with radioactivity, this compound should serve as a reasonable probe of haloalkane anesthetic binding targets and sites.

  DOI：

  10.1021/jm0104926
• 作为产物：
  描述：

  3-chloro-2,2,3-trifluoro-propionic acid ethyl ester 在 氨 作用下， 生成 3-chloro-2,2,3-trifluoro-propionic acid amide
  参考文献：
  名称：

  Halogenated Diazirines as Photolabel Mimics of the Inhaled Haloalkane Anesthetics

  摘要：

  The inhaled anesthetics are low affinity volatile compounds whose mechanism of action remains unclear, in part due to the difficulty of determining their binding targets. Photolabeling may help resolve this difficulty, and thus we have synthesized six compounds (four previously unreported) with structural and physical similarity to halothane (1-bromo-1-chloro-2,2,2-trifluoroethane), a commonly used clinical anesthetic. These compounds incorporate either a diazo, diazirine, or azido group to provide photolability in the long-UV range and to provide a highly reactive photolysis product. While several of the compounds have immobilizing activity in tadpoles, it is complicated by either toxicity or very low potency. One compound however, a halogenated three-carbon diazirine 4, is a potent anesthetic, is apparently nontoxic, potentiates GABA(A) Cl- currents, and stabilizes serum albumin, all of which are features of halothane. When tagged with radioactivity, this compound should serve as a reasonable probe of haloalkane anesthetic binding targets and sites.

  DOI：

  10.1021/jm0104926

文献信息

• Fluorocarboxylic Acids and Amides from Fluoroölefins and Sodium Cyanide
  作者：D. C. England、R. V. Lindsey、L. R. Melby

  DOI：10.1021/ja01556a067

  日期：1958.12
• England; Melby, <1973>239
  作者：England、Melby

  DOI：——

  日期：——
• Halogenated Diazirines as Photolabel Mimics of the Inhaled Haloalkane Anesthetics
  作者：Roderic G. Eckenhoff、Frank J. Knoll、Eric P. Greenblatt、William P. Dailey

  DOI：10.1021/jm0104926

  日期：2002.4.1

  The inhaled anesthetics are low affinity volatile compounds whose mechanism of action remains unclear, in part due to the difficulty of determining their binding targets. Photolabeling may help resolve this difficulty, and thus we have synthesized six compounds (four previously unreported) with structural and physical similarity to halothane (1-bromo-1-chloro-2,2,2-trifluoroethane), a commonly used clinical anesthetic. These compounds incorporate either a diazo, diazirine, or azido group to provide photolability in the long-UV range and to provide a highly reactive photolysis product. While several of the compounds have immobilizing activity in tadpoles, it is complicated by either toxicity or very low potency. One compound however, a halogenated three-carbon diazirine 4, is a potent anesthetic, is apparently nontoxic, potentiates GABA(A) Cl- currents, and stabilizes serum albumin, all of which are features of halothane. When tagged with radioactivity, this compound should serve as a reasonable probe of haloalkane anesthetic binding targets and sites.