(E)-diethyl (phenyl)cinnamidomethylphosphonate | 1006720-00-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-diethyl (phenyl)cinnamidomethylphosphonate
• 英文别名: (E)-Diethyl cinnamamido(phenyl)methylphosphonate；(E)-N-[diethoxyphosphoryl(phenyl)methyl]-3-phenylprop-2-enamide
• CAS: 1006720-00-8
• 化学式: C₂₀H₂₄NO₄P
• 分子量: 373.389
• InChiKey: XGIKTCJMOJQNTJ-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  反-肉桂酰胺 、 diethyl 1-aminophenylmethylphosphonate 在 N,N'-二环己基碳二亚胺 作用下， 以 甲苯 为溶剂， 以80.6%的产率得到(E)-diethyl (phenyl)cinnamidomethylphosphonate
  参考文献：
  名称：

  Synthesis and Antiviral Activities of Amide Derivatives Containing the α-Aminophosphonate Moiety

  摘要：

  Starting from (substituted-)benzaldehydes, the title compounds 6 were synthesized through five step reactions. Benzaldehydes were treated with ammonium hydroxide, followed by dialkyl phosphite, to give dialkyl N-(arylmethylene)-1-amino-1-aryl methylphosphonates (3). Phosphonates 3 were then easily hydrolyzed to give dialkyl 1-amino-1-aryl-methylphosphonates 5. Target compounds 6 were then obtained by the reaction of 5 and substituted benzoic or cinnamic acid. Their structures were clearly verified by spectroscopic data (IR, H-1, C-13, and P-31 NMR, and elemental analysis). These compounds were shown to be antivirally active in the bioassay. It was found that title compounds 6g, 61,,and 6n had the same inactivation effect of TMV (EC50 = 54.8, 60.0, and 65.2 mu g/mL, respectively) as commercial product Ningnanmycin (EC50 = 55.6 mu g/mL). To the best of our knowledge, this is the first report on the synthesis and antiviral activity of amide derivatives containing an alpha-aminophosphonate moiety.

  DOI：

  10.1021/jf072394k

文献信息

• Synthesis and Antiviral Activities of Amide Derivatives Containing the α-Aminophosphonate Moiety
  作者：De-Yu Hu、Qiong-Qiong Wan、Song Yang、Bao-An Song、Pinaki S. Bhadury、Lin-Hong Jin、Kai Yan、Fang Liu、Zhuo Chen、Wei Xue

  DOI：10.1021/jf072394k

  日期：2008.2

  Starting from (substituted-)benzaldehydes, the title compounds 6 were synthesized through five step reactions. Benzaldehydes were treated with ammonium hydroxide, followed by dialkyl phosphite, to give dialkyl N-(arylmethylene)-1-amino-1-aryl methylphosphonates (3). Phosphonates 3 were then easily hydrolyzed to give dialkyl 1-amino-1-aryl-methylphosphonates 5. Target compounds 6 were then obtained by the reaction of 5 and substituted benzoic or cinnamic acid. Their structures were clearly verified by spectroscopic data (IR, H-1, C-13, and P-31 NMR, and elemental analysis). These compounds were shown to be antivirally active in the bioassay. It was found that title compounds 6g, 61,,and 6n had the same inactivation effect of TMV (EC50 = 54.8, 60.0, and 65.2 mu g/mL, respectively) as commercial product Ningnanmycin (EC50 = 55.6 mu g/mL). To the best of our knowledge, this is the first report on the synthesis and antiviral activity of amide derivatives containing an alpha-aminophosphonate moiety.