3-(3-bromophenyl)-5-chloroisoxazole | 51726-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(3-bromophenyl)-5-chloroisoxazole
• 英文别名: 5-Chlor-3-(3-bromphenyl)-isoxazol；3-(3-Bromophenyl)-5-chloroisoxazole；3-(3-bromophenyl)-5-chloro-1,2-oxazole
• CAS: 51726-14-8
• 化学式: C₉H₅BrClNO
• 分子量: 258.502
• InChiKey: CRPHDCBCJNEWBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(3-bromophenyl)-1,1-dichlorocyclopropane 在 nitrosyl chloride sulfur trioxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以85%的产率得到3-(3-bromophenyl)-5-chloroisoxazole
  参考文献：
  名称：

  Transformations of gem-dichloroarylcyclopropanes in the reaction with NOCl·2SO3. Synthesis of 3-aryl-5-chloroisoxazoles

  摘要：

  Nitrosation with complex NOCl center dot 2SO(3) of gem-dichloroarylcyclopropanes containing acceptor substituents in the aromatic ring proceeded chemo- and regioselectively affording 3-aryl-5-chloroisoxazoles in high yields. The presence of donor substituents complicated the reaction by the occurrence of competing processes.

  DOI：

  10.1134/s1070428013020024

文献信息

• Transformations of gem-dichloroarylcyclopropanes in the reaction with NOCl·2SO3. Synthesis of 3-aryl-5-chloroisoxazoles
  作者：O. B. Bondarenko、A. Yu. Gavrilova、D. S. Murodov、N. S. Zefirov、N. V. Zyk

  DOI：10.1134/s1070428013020024

  日期：2013.2

  Nitrosation with complex NOCl center dot 2SO(3) of gem-dichloroarylcyclopropanes containing acceptor substituents in the aromatic ring proceeded chemo- and regioselectively affording 3-aryl-5-chloroisoxazoles in high yields. The presence of donor substituents complicated the reaction by the occurrence of competing processes.
• Nitrosylsulfuric acid in the synthesis of 5-chloroisoxazoles from 1,1-dichlorocyclopropanes
  作者：Oksana B. Bondarenko、Zaur M. Garaev、Arseniy I. Komarov、Lyubov I. Kuznetsova、Svetlana V. Gutorova、Dmitry A. Skvortsov、Nikolai V. Zyk

  DOI：10.1016/j.mencom.2019.07.021

  日期：2019.7

  Nitrosylsulfuric acid is shown to be a usable reagent for the synthesis of 5-chioroisoxazoles from readily available 1,1-dichlorocyclopropanes via nitrosation-heterocyclization reaction. A cytotoxicity of some of the prepared 5-chloroisoxazoles towards MCF7, A549, HEK293T and VA13 cell lines was evaluated.