4-(10-phenothiazinyl)-3-thiazolin-2-one | 117456-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 4-(10-phenothiazinyl)-3-thiazolin-2-one
• 英文别名: 4-phenothiazin-10-yl-5H-1,3-thiazol-2-one
• CAS: 117456-42-5
• 化学式: C₁₅H₁₀N₂OS₂
• 分子量: 298.389
• InChiKey: WGQGYAGQCOHMBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  10-(氯乙酰基)-10H-吩噻嗪 以 丙酮 、 苯 为溶剂， 反应 194.0h， 生成 4-(10-phenothiazinyl)-3-thiazolin-2-one
  参考文献：
  名称：

  Reactions of phenothiazine thiocyanate derivatives with dialkyldithiophosphoric acids

  摘要：

  The addition products of dialkyldithiophosphoric acids to the C = N bond in 3-thiocyanatophenothiazine rearrange to give relatively more stable S-(3-phenothiazinyl)-N-dialkoxythiophosphoryldithiocarbamates. An analogous derivative, formed in the reaction of diethyldithiophosphoric acid with 3-thiocyanato-10-ethylphenothiazine, is unstable and decomposes to give 3-mercapto-10-ethylphenothiazine and diethylisothiocyanatothiophosphate. The main pathway in the reaction of dialkyldithiophosphoric acids with 10-(thiocyanatoacetyl)phenothiazine appears to be acid-catalyzed cyclization of the latter to give 4-(10-phenothiazinyl)-3-thiazolin-2-one. However, the formation of 3-dialkoxythiophosphoryl-4-thiazolidinone-2-thiones is also observed in these reactions; these products result from rearrangement of the addition products of dithio acids to C = N bonds, followed by subsequent heterocyclization via elimination of phenothiazine. The molecular structure of 3-diisopropoxythiophosphoryl-4-thiazolidinone-2-thione was investigated by x-ray structural analysis; the heterocyclic fragment in this molecule exists in an envelope conformation with the nitrogen atom deviating from the plane of the other four atoms.

  DOI：

  10.1007/bf00965438

文献信息

• Reactions of phenothiazine thiocyanate derivatives with dialkyldithiophosphoric acids
  作者：R. M. Kamalov、G. M. Makarov、O. N. Kataeva、R. Z. Musin、I. A. Litvinov、Kh. Al'-Akra、M. A. Pudovik

  DOI：10.1007/bf00965438

  日期：1991.2

  The addition products of dialkyldithiophosphoric acids to the C = N bond in 3-thiocyanatophenothiazine rearrange to give relatively more stable S-(3-phenothiazinyl)-N-dialkoxythiophosphoryldithiocarbamates. An analogous derivative, formed in the reaction of diethyldithiophosphoric acid with 3-thiocyanato-10-ethylphenothiazine, is unstable and decomposes to give 3-mercapto-10-ethylphenothiazine and diethylisothiocyanatothiophosphate. The main pathway in the reaction of dialkyldithiophosphoric acids with 10-(thiocyanatoacetyl)phenothiazine appears to be acid-catalyzed cyclization of the latter to give 4-(10-phenothiazinyl)-3-thiazolin-2-one. However, the formation of 3-dialkoxythiophosphoryl-4-thiazolidinone-2-thiones is also observed in these reactions; these products result from rearrangement of the addition products of dithio acids to C = N bonds, followed by subsequent heterocyclization via elimination of phenothiazine. The molecular structure of 3-diisopropoxythiophosphoryl-4-thiazolidinone-2-thione was investigated by x-ray structural analysis; the heterocyclic fragment in this molecule exists in an envelope conformation with the nitrogen atom deviating from the plane of the other four atoms.