(2-Amino-3,5-dicyano-6-hydroxy-4-methyl-phenyl)-phosphonic acid diethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2-Amino-3,5-dicyano-6-hydroxy-4-methyl-phenyl)-phosphonic acid diethyl ester
• 英文别名: 4-Amino-5-diethoxyphosphoryl-6-hydroxy-2-methylbenzene-1,3-dicarbonitrile
• 化学式: C₁₃H₁₆N₃O₄P
• 分子量: 309.261
• InChiKey: CHVFQBZVYPKFEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (4-Amino-3-cyano-2-oxo-pent-3-enyl)-phosphonic acid diethyl ester 、 丙二腈 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以91%的产率得到(2-Amino-3,5-dicyano-6-hydroxy-4-methyl-phenyl)-phosphonic acid diethyl ester
  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

表征谱图