Cyanessigsaeure-β-phenoxyethyl-ester | 32804-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Cyanessigsaeure-β-phenoxyethyl-ester
• 英文别名: Acetic acid, 2-cyano-, 2-phenoxyethyl ester；2-phenoxyethyl 2-cyanoacetate
• CAS: 32804-78-7
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: JDWZQOGWSGQVPB-UHFFFAOYSA-N

物化性质

• 沸点：
  347.2±17.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Cyanessigsaeure-β-phenoxyethyl-ester 在 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
• 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 、 氰乙酸乙酯 在 sodium hydride 作用下， 生成 Cyanessigsaeure-β-phenoxyethyl-ester
  参考文献：
  名称：

  Schulze,W., Journal fur praktische Chemie (Leipzig 1954), 1972, vol. 314, p. 649 - 654

  摘要：

  DOI：

文献信息

• Etlis,V.S. et al., Journal of applied chemistry of the USSR, 1971, vol. 44, p. 944 - 946
  作者：Etlis,V.S. et al.

  DOI：——

  日期：——
• Novel caffeic acid derivatives: extremely potent inhibitors of 12-lipoxygenase
  作者：Hidetsura Cho、Masaru Ueda、Mie Tamaoka、Mikiko Hamaguchi、Kazuo Aisaka、Yoshinobu Kiso、Teruyoshi Inoue、Ryoko Ogino、Toshio Tatsuoka

  DOI：10.1021/jm00108a039

  日期：1991.4
• Phillips, John N.; Huppatz, John L., Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 55 - 58
  作者：Phillips, John N.、Huppatz, John L.

  DOI：——

  日期：——
• Etlis,V.S. et al., Journal of applied chemistry of the USSR, 1972, vol. 45, p. 217 - 220
  作者：Etlis,V.S. et al.

  DOI：——

  日期：——
• US4018796A
  申请人：——

  公开号：US4018796A

  公开（公告）日：1977-04-19