1-(4-Chlor-phenyl)-2-(2-chlor-phenyl)-1-cyan-ethylen

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(4-Chlor-phenyl)-2-(2-chlor-phenyl)-1-cyan-ethylen
• 英文别名: 3-<2-Chlor-phenyl>-2-<4-chlor-phenyl>-acrylnitril；2',4-Dichlor-α-cyan-stilben；3-(2-Chlorophenyl)-2-(4-chlorophenyl)prop-2-enenitrile
• 化学式: C₁₅H₉Cl₂N
• 分子量: 274.149
• InChiKey: OQWNYEUXPHZVMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二氯胺T 、 1-(4-Chlor-phenyl)-2-(2-chlor-phenyl)-1-cyan-ethylen 在 copper(l) chloride 、 sodium sulfite 、 三乙胺 作用下， 以 乙腈 、 水 为溶剂， 反应 24.5h， 以43%的产率得到3-(2-chlorophenyl)-2-(4-chlorophenyl)-1-tosylaziridine-2-carbonitrile
  参考文献：
  名称：

  One-Pot Highly Stereoselective Synthesis of Cyano Aziridines via the CuCl-Catalyzed Aminochlorination of α,β-Unsaturated Nitriles and Intramolecular SN2 Substitution

  摘要：

  An efficient one‐pot system has been developed for the synthesis of cyano aziridine by using α,β‐unsaturated nitriles as the alkene substrates and N,N‐dichloro‐p‐toluenesulfonamide (4‐TsNCl2) as the nitrogen source. A good scope of alkene substrates was achieved for this reaction. The one‐pot reaction, via aminohalogenation and intramolecular SN2 substitution, was very convenient to carry out at room temperature without the protection of inert gases. Modest to good yields and excellent have been obtained. This method provides an easy route to the cyano aziridine. The structure of the resulting products has been unambiguously confirmed by X‐ray structural analysis.

  DOI：

  10.1111/j.1747-0285.2010.01023.x

文献信息

• One-Pot Highly Stereoselective Synthesis of Cyano Aziridines via the CuCl-Catalyzed Aminochlorination of α,β-Unsaturated Nitriles and Intramolecular SN2 Substitution
  作者：Haibo Mei、Lijun Yan、Jianlin Han、Guigen Li、Yi Pan

  DOI：10.1111/j.1747-0285.2010.01023.x

  日期：2010.11

  An efficient one‐pot system has been developed for the synthesis of cyano aziridine by using α,β‐unsaturated nitriles as the alkene substrates and N,N‐dichloro‐p‐toluenesulfonamide (4‐TsNCl2) as the nitrogen source. A good scope of alkene substrates was achieved for this reaction. The one‐pot reaction, via aminohalogenation and intramolecular SN2 substitution, was very convenient to carry out at room temperature without the protection of inert gases. Modest to good yields and excellent have been obtained. This method provides an easy route to the cyano aziridine. The structure of the resulting products has been unambiguously confirmed by X‐ray structural analysis.