3-chloro-5-(phenylthio)isothiazole-4-carbonitrile | 3889-64-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-chloro-5-(phenylthio)isothiazole-4-carbonitrile
• 英文别名: 3-chloro-5-phenylsulfanyl-isothiazole-4-carbonitrile；3-Chlor-5-phenylmercapto-4-cyan-isothiazol；3-Chloro-5-phenylsulfanyl-1,2-thiazole-4-carbonitrile；3-chloro-5-phenylsulfanyl-1,2-thiazole-4-carbonitrile
• CAS: 3889-64-3
• 化学式: C₁₀H₅ClN₂S₂
• 分子量: 252.748
• InChiKey: KPUFYGJZDWIYRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 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：
  90.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-5-(phenylthio)isothiazole-4-carbonitrile 在 肼 作用下， 反应 0.08h， 以90%的产率得到3-chloro-5-hydrazinylisothiazole-4-carbonitrile
  参考文献：
  名称：

  The conversion of isothiazoles into pyrazoles using hydrazine

  摘要：

  The conversion of isothiazoles into pyrazoles on treatment with hydrazine is investigated. The influence of various C-3, C-4 and C-5 isothiazole substituents and some limitations of this ring transformation are examined. When the isothiazole C-3 substituent is a good nucleofuge, 3-aminopyrazoles are obtained. However, when the 3-substituent is not a leaving group it is retained in the pyrazole product. Treatment of 4-bromo-3-chloro-5-phenylisothiazoie 56 or 3-chloro-4,5-diphenylisothiazole 57 with anhydrous hydrazine at ca. 200 degrees C for a few minutes gives the corresponding 3-hydrazinoisothiazoles 61 and 64 respectively in high yields; the stability of these new hydrazines is investigated. 5,5'-Diphenyl-3,3'-biisothiazole-4,4'-dicarbonitrile 78 reacts with hydrazine to give 5,5'-diphenyl-3,3'-bi(1H-pyi-azole)-4,4'-dicarbonitrile 79. Methylhydrazine reacts with 3-chloro-5-phenytisothiazole-4-carbonitrile 1 to give 3-(1-methylhydrazino)-5-phenylisothiazole-4-carbontrile 83 and 3-amino-lmethyl-5-phenylpyrazole-4-carbonitrile 84. All products are fully characterised and rational mechanisms for the isothiazole into pyrazole transformation are proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.041
• 作为产物：
  描述：

  3,5-二氯-4-异噻唑甲腈 生成 3-chloro-5-(phenylthio)isothiazole-4-carbonitrile
  参考文献：
  名称：

  The Synthesis of Isothiazoles. I. 3,5-Dichloro-4-isothiazolecarbonitrile and Its Derivatives

  摘要：

  DOI：

  10.1021/jo01026a033