2-phenoxyethyl 3-[[bis(2-ethoxyethoxy)phosphoryl-phenylmethyl]amino]-2-cyano-3-methylsulfanylprop-2-enoate | 1202935-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-phenoxyethyl 3-[[bis(2-ethoxyethoxy)phosphoryl-phenylmethyl]amino]-2-cyano-3-methylsulfanylprop-2-enoate
• CAS: 1202935-39-4
• 化学式: C₂₈H₃₇N₂O₈PS
• 分子量: 592.65
• InChiKey: WNPCLQNTPYWHPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  40.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  125.34
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  己二酸,聚合2,2-二甲基-1,3-丙二醇和2,5-呋喃二酮,苯酸酯 在 硫酸 、 potassium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 100.0 ℃ 、689.49 kPa 条件下， 反应 2.0h， 生成 2-phenoxyethyl 3-[[bis(2-ethoxyethoxy)phosphoryl-phenylmethyl]amino]-2-cyano-3-methylsulfanylprop-2-enoate
  参考文献：
  名称：

  Synthesis and Antiviral Bioactivities of 2-Cyano-3-substituted-amino(phenyl) Methylphosphonylacrylates (Acrylamides) Containing Alkoxyethyl Moieties

  摘要：

  An efficient reaction under microwave irradiation has been developed for the synthesis of a series of novel 2-cyano-3-substituted-amino(phenyl) methylphosphonylacrylates (acrylamides) II. The products obtained in shorter reaction time with moderate yields are fully characterized by elemental analysis, IR, H-1, C-13, and P-31 NMR spectral data. The role of introducing various substituents and the effect of incorporating alpha-aminophosphonates with an alkoxyethyl moiety into the parent cyanoacrylate (acrylamide) structure are investigated. Among the studied compounds, both II-17 and II-24 displayed good in vivo curative, protection, and inactivation effects, which were comparable to those of the commercial reference ningnanmycin (inhibitory rates of 58.8, 60.2, 78.9% and 60.0, 58.9, 85.5%, respectively, at 500 mg/L against TMV). To the best of the authors' knowledge, this is the first report on the synthesis and antiviral activity of the title compounds II.

  DOI：

  10.1021/jf902861m

文献信息

• Synthesis and Antiviral Bioactivities of 2-Cyano-3-substituted-amino(phenyl) Methylphosphonylacrylates (Acrylamides) Containing Alkoxyethyl Moieties
  作者：Jia-Qiang Yang、Bao-an Song、Pinaki S. Bhadury、Zhuo Chen、Song Yang、Xue-Jian Cai、De-Yu Hu、Wei Xue

  DOI：10.1021/jf902861m

  日期：2010.3.10

  An efficient reaction under microwave irradiation has been developed for the synthesis of a series of novel 2-cyano-3-substituted-amino(phenyl) methylphosphonylacrylates (acrylamides) II. The products obtained in shorter reaction time with moderate yields are fully characterized by elemental analysis, IR, H-1, C-13, and P-31 NMR spectral data. The role of introducing various substituents and the effect of incorporating alpha-aminophosphonates with an alkoxyethyl moiety into the parent cyanoacrylate (acrylamide) structure are investigated. Among the studied compounds, both II-17 and II-24 displayed good in vivo curative, protection, and inactivation effects, which were comparable to those of the commercial reference ningnanmycin (inhibitory rates of 58.8, 60.2, 78.9% and 60.0, 58.9, 85.5%, respectively, at 500 mg/L against TMV). To the best of the authors' knowledge, this is the first report on the synthesis and antiviral activity of the title compounds II.