4-Cyanimino-3-cyano-4-phenyl-1-pyridinio-but-2-en-2-enolate | 170652-89-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-Cyanimino-3-cyano-4-phenyl-1-pyridinio-but-2-en-2-enolate
• 英文别名: [2-(N-cyano-C-phenylcarbonimidoyl)-3-oxo-4-pyridin-1-ium-1-ylbut-1-enylidene]azanide
• CAS: 170652-89-8
• 化学式: C₁₇H₁₂N₄O
• 分子量: 288.308
• InChiKey: ZGMLSYBIBVTHSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Cyanimino-3-cyano-4-phenyl-1-pyridinio-but-2-en-2-enolate 在 盐酸 、 sodium perchlorate 作用下， 以93%的产率得到1-(4-Cyanimino-3-cyano-2-hydroxy-4-phenyl-but-2-en-1-yl)-pyridinium perchlorate
  参考文献：
  名称：

  Syntheses with pyridinium and sulfonium salts of acylated ?-enaminonitriles

  摘要：

  Pyridinium and sulfonium salts 2a-e which can be prepared from 3-amino-2-(alpha-haloacetyl)-crotonitriles and 3-amino-2-(alpha-halo-acetyl)-3-phenyl-acrylonitriles react with malononitrile in the presence of a base to 3-amino-2-pyridinio-phenolates 3a,b and 3-amino-2-sulfonio-phenolates 3c-e. In an analogous way, 3-amino-2-(diethyloxyphosphoryl)-phenol 5a and 3-amino-2-(p-tolyl-sulfonyl)phenol 5b have been prepared. 2,3-Diamino-phenoles 6a,b are formed from the pyridinium salts 3a,b. The behaviour of the pyridinium salts 2a,b towards heterocumulenes has been investigated. Cyanamide leads to the (2-amino-4-hydroxy-pyrid-3-yl)-pyridinium salt 8c. Phenylisothiocyanate gives the 3-pyridinio-2-thioxo-pyridin-4-olates 9a,b. Carbon disulfide gives rise to 3-pyridinio-2-thioxo-pyridin-4-olate 10 or 3-pyridinio-2-thioxo-thiopyran-4-olate 11, depending on the substituent at the g-position. Phenylisocyanate reacts to the pyrimidin-2,4-dione 12 with loss of N-methyl-pyridinium chloride. S-methylation of 9a and cleavage of the pyridine moiety yields the 3-amino-2-methylthio-pyrid-4-one 14. The structures were investigated by H-1 and C-13 NMR spectroscopy.

  DOI：

  10.1007/bf00807162
• 作为产物：
  描述：

  氰胺 、 1-(4-Amino-3-cyano-2-oxo-4-phenyl-but-3-en-1-yl)-pyridinium chloride 在 ammonium hydroxide 作用下， 以52%的产率得到4-Cyanimino-3-cyano-4-phenyl-1-pyridinio-but-2-en-2-enolate
  参考文献：
  名称：

  Syntheses with pyridinium and sulfonium salts of acylated ?-enaminonitriles

  摘要：

  Pyridinium and sulfonium salts 2a-e which can be prepared from 3-amino-2-(alpha-haloacetyl)-crotonitriles and 3-amino-2-(alpha-halo-acetyl)-3-phenyl-acrylonitriles react with malononitrile in the presence of a base to 3-amino-2-pyridinio-phenolates 3a,b and 3-amino-2-sulfonio-phenolates 3c-e. In an analogous way, 3-amino-2-(diethyloxyphosphoryl)-phenol 5a and 3-amino-2-(p-tolyl-sulfonyl)phenol 5b have been prepared. 2,3-Diamino-phenoles 6a,b are formed from the pyridinium salts 3a,b. The behaviour of the pyridinium salts 2a,b towards heterocumulenes has been investigated. Cyanamide leads to the (2-amino-4-hydroxy-pyrid-3-yl)-pyridinium salt 8c. Phenylisothiocyanate gives the 3-pyridinio-2-thioxo-pyridin-4-olates 9a,b. Carbon disulfide gives rise to 3-pyridinio-2-thioxo-pyridin-4-olate 10 or 3-pyridinio-2-thioxo-thiopyran-4-olate 11, depending on the substituent at the g-position. Phenylisocyanate reacts to the pyrimidin-2,4-dione 12 with loss of N-methyl-pyridinium chloride. S-methylation of 9a and cleavage of the pyridine moiety yields the 3-amino-2-methylthio-pyrid-4-one 14. The structures were investigated by H-1 and C-13 NMR spectroscopy.

  DOI：

  10.1007/bf00807162

文献信息

• Syntheses with pyridinium and sulfonium salts of acylated ?-enaminonitriles
  作者：K. Gewald、M. Rehwald、K. Eckert、H. Sch�fer、M. Gruner

  DOI：10.1007/bf00807162

  日期：——

  Pyridinium and sulfonium salts 2a-e which can be prepared from 3-amino-2-(alpha-haloacetyl)-crotonitriles and 3-amino-2-(alpha-halo-acetyl)-3-phenyl-acrylonitriles react with malononitrile in the presence of a base to 3-amino-2-pyridinio-phenolates 3a,b and 3-amino-2-sulfonio-phenolates 3c-e. In an analogous way, 3-amino-2-(diethyloxyphosphoryl)-phenol 5a and 3-amino-2-(p-tolyl-sulfonyl)phenol 5b have been prepared. 2,3-Diamino-phenoles 6a,b are formed from the pyridinium salts 3a,b. The behaviour of the pyridinium salts 2a,b towards heterocumulenes has been investigated. Cyanamide leads to the (2-amino-4-hydroxy-pyrid-3-yl)-pyridinium salt 8c. Phenylisothiocyanate gives the 3-pyridinio-2-thioxo-pyridin-4-olates 9a,b. Carbon disulfide gives rise to 3-pyridinio-2-thioxo-pyridin-4-olate 10 or 3-pyridinio-2-thioxo-thiopyran-4-olate 11, depending on the substituent at the g-position. Phenylisocyanate reacts to the pyrimidin-2,4-dione 12 with loss of N-methyl-pyridinium chloride. S-methylation of 9a and cleavage of the pyridine moiety yields the 3-amino-2-methylthio-pyrid-4-one 14. The structures were investigated by H-1 and C-13 NMR spectroscopy.