3-(phenoxymethyl)-3-bromodiazirine | 154197-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(phenoxymethyl)-3-bromodiazirine
• 英文别名: 3-Bromo-3-(phenoxymethyl)diazirine
• CAS: 154197-61-2
• 化学式: C₈H₇BrN₂O
• 分子量: 227.06
• InChiKey: UGBJOWHBBDVNEH-UHFFFAOYSA-N

物化性质

• 沸点：
  257.3±50.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(phenoxymethyl)-3-bromodiazirine 在 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Kinetics of alkylhalocarbene rearrangements: modulation by fluorine substituents

  摘要：

  Rate constants were measured by laser flash photolytic methods for hydrogen and carbon 1,2-migrations in four different alkylchlorocarbenes and in the analogous alkylfluorocarbenes. The carbenes, products, and rate constants (s-1) were as follows: phenoxymethylchlorocarbene to (Z)- and (E)-1-chloro-2-phenoxyethene (Z/E approximately 4/1), k = 3.6 x 10(7); phenoxymethylfluorocarbene to (Z)-1-fluoro-2-phenoxyethene (Z/E > 10/1), k = 1.3 x 10(7); neopentylchlorocarbene to (Z)- and (E)-1-tert-butyl-2-chloroethene (Z/E = 1/12), k = 1.4 x 10(7); neopentylfluorocarbene to (Z)- and (E)-1-tert-butyl-2-fluoroethene (Z/E = 1/2.5), k = 2.6 X 10(6); cyclobutylchlorocarbene to 1-chlorocyclopentene (C migration) and chloromethylenecyclobutane (H migration), k(c) = 4.6 X 10(7), k(H) = 2.1 X 10(7); cyclobutylfluorocarbene to 1-fluorocyclopentene (C migration) and fluoromethylenecyclobutane (H migration), k(c) = 1.8 x 10(6), k(H) = 5.3 x 10(5); cyclopropylchlorocarbene to 1-chlorocyclobutene, k = 9 x 10(5); cyclopropylfluorocarbene to 1-fluorocyclobutene, k = 1.4 x 10(5). Activation energies for several of these processes were in the range of 2-4 kcal/mol, with A approximately 10(8)-10(9) s-1.

  DOI：

  10.1021/ja00029a025
• 作为产物：
  描述：

  2-苯氧基乙脒盐酸盐 在 sodium hypobromide 、 lithium bromide 作用下， 以 二甲基亚砜 、 正戊烷 为溶剂， 反应 1.0h， 生成 3-(phenoxymethyl)-3-bromodiazirine
  参考文献：
  名称：

  Kinetics of alkylhalocarbene rearrangements: modulation by fluorine substituents

  摘要：

  Rate constants were measured by laser flash photolytic methods for hydrogen and carbon 1,2-migrations in four different alkylchlorocarbenes and in the analogous alkylfluorocarbenes. The carbenes, products, and rate constants (s-1) were as follows: phenoxymethylchlorocarbene to (Z)- and (E)-1-chloro-2-phenoxyethene (Z/E approximately 4/1), k = 3.6 x 10(7); phenoxymethylfluorocarbene to (Z)-1-fluoro-2-phenoxyethene (Z/E > 10/1), k = 1.3 x 10(7); neopentylchlorocarbene to (Z)- and (E)-1-tert-butyl-2-chloroethene (Z/E = 1/12), k = 1.4 x 10(7); neopentylfluorocarbene to (Z)- and (E)-1-tert-butyl-2-fluoroethene (Z/E = 1/2.5), k = 2.6 X 10(6); cyclobutylchlorocarbene to 1-chlorocyclopentene (C migration) and chloromethylenecyclobutane (H migration), k(c) = 4.6 X 10(7), k(H) = 2.1 X 10(7); cyclobutylfluorocarbene to 1-fluorocyclopentene (C migration) and fluoromethylenecyclobutane (H migration), k(c) = 1.8 x 10(6), k(H) = 5.3 x 10(5); cyclopropylchlorocarbene to 1-chlorocyclobutene, k = 9 x 10(5); cyclopropylfluorocarbene to 1-fluorocyclobutene, k = 1.4 x 10(5). Activation energies for several of these processes were in the range of 2-4 kcal/mol, with A approximately 10(8)-10(9) s-1.

  DOI：

  10.1021/ja00029a025

文献信息

• Acetoxycarbenes: Modified Oxacarbenes with Enhanced Reactivity
  作者：Robert A. Moss、Song Xue、Weiguo Liu

  DOI：10.1021/ja00083a059

  日期：1994.2