2-endo-bromo-3-exo-chlorobicyclo<2.2.1>heptane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-endo-bromo-3-exo-chlorobicyclo<2.2.1>heptane
• 英文别名: endo-2-bromo-exo-3-chlorobicyclo[2.2.1]heptane；5-Chlor-6-brom-norbornan；(1R,2R,3R,4S)-2-bromo-3-chlorobicyclo[2.2.1]heptane
• 化学式: C₇H₁₀BrCl
• 分子量: 209.513
• InChiKey: MFXKLVIFXLYPMA-XZBKPIIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  降冰片烯 在 n-氯吗啉 、 三溴氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以44%的产率得到2-endo-bromo-3-exo-chlorobicyclo<2.2.1>heptane
  参考文献：
  名称：

  A NEW METHOD FOR MIXED HALOGENATION. N-CHLOROAMINE-PHOSPHORUS BROMIDE SYSTEM AS A SYNTHETIC EQUIVALENT OF THE MIXED HALOGEN Cl⁺Br⁻

  摘要：

  A new method for the mixed halogenation of alkenes has been proposed based on the reaction of olefins with N-chloroamines in the presence of phosphorus bromide or oxybromide. The plausible reaction mechanism and the results of reactions with a number of model unsaturated compounds such as cyclohexene, 1-heptene. ethyl cinnamate, norbornene and those from the bicyclo[2.2.1]heptane series are discussed. In the reactions with reactive olefins this reagent acts as a synthetic equivalent of the unknown mixed halogen [Cl+Br-] with "abnormal" polarity of halogen atoms. The same reactions activated by PCl3 or POCl3 result in dichlorides in yields near to quantitative.

  DOI：

  10.1080/10426509808035682

文献信息

• Regio- and stereochemical aspects of bromochlorination of norbornene
  作者：N. V. Zyk、E. K. Beloglazkina、V. S. Tyurin、Yu. K. Grishin

  DOI：10.1007/bf02494285

  日期：1998.11

  type of the halogenating reagent used was studied. Three isomeric bromochloronorbornanes (2-endo-bromo-3-exo-chloro-, 2-exo-bromo-3-endo-chloro-, and 2-exo-bromo-7-syn-chlorobicyclo[2.2.1.]heptanes), 2-exo-7-syn- and 2-exo-7-anti-dibromo- and-dichloronorbornanes, and 2-bromonortricyclane were isolated and characterized by1H and13C NMR spectra. The spectral and structural characteristics of the resulting

  研究了降冰片烯的溴氯化，其化学和区域选择性取决于所用卤化剂的类型。三种异构溴氯降冰片烷（2-endo-bromo-3-exo-chloro-、2-exo-bromo-3-endo-chloro-和 2-exo-bromo-7-syn-chlorobicyclo[2.2.1.]heptanes） 2-exo-7-syn-和2-exo-7-anti-dibromo-and-dichloronorbornanes和2-bromonortricyclane被分离出来，并通过1H和13C NMR光谱表征。讨论了所得化合物的光谱和结构特征。

表征谱图