3-bromo-3-chloro-2,2-difluoropropionimidic acid methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: 3-bromo-3-chloro-2,2-difluoropropionimidic acid methyl ester
• 英文别名: Methyl 3-bromo-3-chloro-2,2-difluoropropanimidate
• 化学式: C₄H₅BrClF₂NO
• 分子量: 236.444
• InChiKey: UDYFVPMMARZYSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromo-3-chloro-2,2-difluoropropionimidic acid methyl ester 在 盐酸 作用下， 反应 0.25h， 以75%的产率得到3-bromo-3-chloro-2,2-difluoropropionic acid methyl ester
  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：

  甲醇 、 1,2-二溴-1-氯-2,2-二氟乙烷 、 氰化钾 以 水 为溶剂， 反应 2.0h， 以70%的产率得到3-bromo-3-chloro-2,2-difluoropropionimidic acid methyl ester
  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