cyclobutylchlorodiazirine | 71690-88-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: cyclobutylchlorodiazirine
• 英文别名: 3-cyclobutyl-3-chlorodiazirine；3-Chlor-3-cyclobutyl-diazirin；3-chloro-3-cyclobutyl-3H-diazirine；3-Chloro-3-cyclobutyldiazirine
• CAS: 71690-88-5
• 化学式: C₅H₇ClN₂
• 分子量: 130.577
• InChiKey: FPNNCXLUAQFSMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  142.5±50.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cyclobutylchlorodiazirine 以 氘代氯仿 为溶剂， 生成 1-氯-1-环戊烯 、 chloromethylenecyclobutane
  参考文献：
  名称：

  Competitive kinetics of 1,2-carbon and hydride shifts in cyclobutylchlorocarbene

  摘要：

  DOI：

  10.1016/s0040-4039(00)88771-7
• 作为产物：
  描述：

  盐酸环丁烷羰基脒 在 水 、 氯 、 lithium chloride 、 sodium chloride 作用下， 以 二甲基亚砜 、 正戊烷 为溶剂， 反应 1.0h， 生成 cyclobutylchlorodiazirine
  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

• Competitive rearrangements of alkylacetoxycarbenes
  作者：Robert A Moss、Song Xue、Wei Ma、Huarong Ma

  DOI：10.1016/s0040-4039(97)00936-2

  日期：1997.6

  Absolute rate constants are determined for (1,2) acetyl, carbon, and hydride shifts in cyclobutylacetoxycarbene and isopropylacetoxycarbene; comparative reactivities are examined.

  确定环丁基乙酰氧基卡宾和异丙基乙酰氧基卡宾中的（1,2）乙酰基，碳原子和氢化物位移的绝对速率常数；比较了反应性。