3,3-dimethylthio-2-cyanopropenoic acid phenoxyethyl ester | 863313-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,3-dimethylthio-2-cyanopropenoic acid phenoxyethyl ester
• 英文别名: 2-Phenoxyethyl 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoate
• CAS: 863313-03-5
• 化学式: C₁₄H₁₅NO₃S₂
• 分子量: 309.41
• InChiKey: BRASIGWTBAGRAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3-dimethylthio-2-cyanopropenoic acid phenoxyethyl ester 、 bis(2-ethoxyethyl) (amino(phenyl)methyl)phosphonate 以 乙醇 为溶剂， 100.0 ℃ 、689.49 kPa 条件下， 反应 0.5h， 以44%的产率得到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：

  Cyanessigsaeure-β-phenoxyethyl-ester 在 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 3,3-dimethylthio-2-cyanopropenoic acid phenoxyethyl ester
  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

• 一种含苯并三氮唑苯基单元的氰基丙烯酸酯 化合物的制备方法及其应用
  申请人：南通大学

  公开号：CN110372618B

  公开（公告）日：2021-10-01

  本发明涉及一种含苯并三氮唑苯基单元的氰基丙烯酸酯化合物(I)的制备方法及其应用。通过苯并三氮唑苄胺化合物与2‑氰基‑3,3‑双(甲硫基)丙烯酸酯反应得到。所述一种含苯并三氮唑苯基单元的氰基丙烯酸酯化合物对阔叶杂草呈现良好的防除效果，该化合物可用于制备农业、园艺等领域的除草剂。
• 一种含1，2，4-三唑苯甲胺基单元的2-氰基丙 烯酸酯衍生物的制备和用途
  申请人：南通大学

  公开号：CN110818649B

  公开（公告）日：2021-10-22

  本发明涉及一种含1，2，4‑三唑苯甲胺基单元的2‑氰基丙烯酸酯衍生物(I)的制备和用途。通过1，2，4‑三唑苯甲胺化合物与2‑氰基‑3,3‑双(甲硫基)丙烯酸酯缩合形成。所述一种含1，2，4‑三唑苯甲胺基单元的2‑氰基丙烯酸酯衍生物对阔叶杂草显示出良好的除草活性，该化合物可用于制备农业、园艺等领域的除草剂。
• 含三氮唑杂环取代的氰基丙烯酸酯类化合物 及其制备方法和用途
  申请人：南通大学

  公开号：CN107556253B

  公开（公告）日：2019-11-01

  本发明涉及一种含三氮唑杂环取代的氰基丙烯酸酯类化合物(I)及其制备方法和应用。以4‑(1H‑1,2,3‑三氮唑‑1‑基)苄胺(II)与2‑氰基‑3,3‑二甲硫基丙烯酸取代酯(III)反应得到。所述含三氮唑杂环取代的氰基丙烯酸酯类化合物对阔叶杂草和禾本科杂草具有较好的防治效果，该化合物可用于制备农业、园艺等领域的除草剂。