10-(thiocyanatoacetyl)phenothiazine | 117456-43-6

• 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: 10-(thiocyanatoacetyl)phenothiazine
• 英文别名: (2-Oxo-2-phenothiazin-10-ylethyl) thiocyanate
• CAS: 117456-43-6
• 化学式: C₁₅H₁₀N₂OS₂
• 分子量: 298.389
• InChiKey: LKQWYCHLNLZIPG-UHFFFAOYSA-N

物化性质

• 熔点：
  179-179.5 °C(Solv: chloroform (67-66-3))
• 沸点：
  571.2±39.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-(thiocyanatoacetyl)phenothiazine 在 二硫代磷酸-O,O-二(1-甲基乙基)酯 作用下， 以 苯 为溶剂， 反应 192.0h， 以17%的产率得到diisopropoxythiophosphoryl-4-thiazolidinone-2-thione
  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
• 作为产物：
  描述：

  吩噻嗪 以 甲苯 、 乙腈 为溶剂， 反应 5.0h， 生成 10-(thiocyanatoacetyl)phenothiazine
  参考文献：
  名称：

  一种三环类化合物、其制备方法及其应用

  摘要：

  本发明公开了一种三环类化合物、其制备方法及其应用。本发明的三环类化合物为如式I所示的化合物、其药学上可接受的盐、其溶剂合物、其药学上可接受的盐的溶剂合物或其晶型。本发明化合物在蛋白水平上抑制病毒复制，且抑制效果强，剂量小，进一步本发明化合物在细胞水平上抑制病毒复制。

  公开号：

  CN115554303A

文献信息

• KAMALOV, R. M.;MAKAROV, G. M.;KATAEVA, O. N.;MUSIN, R. Z.;LITVINOV, I. A.+, IZV. AN CCCP. CEP. XIM.,(1991) N, S. 460-467
  作者：KAMALOV, R. M.、MAKAROV, G. M.、KATAEVA, O. N.、MUSIN, R. Z.、LITVINOV, I. A.+

  DOI：——

  日期：——
• 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.
• 一种三环类化合物、其制备方法及其应用
  申请人：上海科技大学

  公开号：CN115554303A

  公开（公告）日：2023-01-03

  本发明公开了一种三环类化合物、其制备方法及其应用。本发明的三环类化合物为如式I所示的化合物、其药学上可接受的盐、其溶剂合物、其药学上可接受的盐的溶剂合物或其晶型。本发明化合物在蛋白水平上抑制病毒复制，且抑制效果强，剂量小，进一步本发明化合物在细胞水平上抑制病毒复制。