2-(3-nitrophenyl)-1,1-dichlorocyclopropane | 145490-91-1

• 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: 2-(3-nitrophenyl)-1,1-dichlorocyclopropane
• 英文别名: 1-(2,2-Dichlorocyclopropyl)-3-nitrobenzene
• CAS: 145490-91-1
• 化学式: C₉H₇Cl₂NO₂
• 分子量: 232.066
• InChiKey: HZFZMWBSQZBEFX-UHFFFAOYSA-N

物化性质

• 沸点：
  336.0±42.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-nitrophenyl)-1,1-dichlorocyclopropane 在 亚硝基硫酸 作用下， 以 硝基甲烷 为溶剂， 反应 3.0h， 以85%的产率得到5-氯-3-(3-硝基苯基)-1,2-恶唑
  参考文献：
  名称：

  Nitrosylsulfuric acid in the synthesis of 5-chloroisoxazoles from 1,1-dichlorocyclopropanes

  摘要：

  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.

  DOI：

  10.1016/j.mencom.2019.07.021

文献信息

• Lin, Shao-Tao; Yang, Fu-May, Journal of Chemical Research, Miniprint, 1996, # 6, p. 1554 - 1564
  作者：Lin, Shao-Tao、Yang, Fu-May

  DOI：——

  日期：——
• 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.
• Reaction of Halogenated Cyclopropanes and Nitrosyl Cation:  Preparation of Isoxazoles
  作者：Shaw-Tao Lin、Shing-Huey Kuo、Fu-May Yang

  DOI：10.1021/jo962297i

  日期：1997.7.1
• 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.