(E)-ethyl 2-(diethoxyphosphoryl)-3-(pyridin-2-ylamino)acrylate | 1227779-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-ethyl 2-(diethoxyphosphoryl)-3-(pyridin-2-ylamino)acrylate
• 英文别名: ethyl (E)-2-[diethoxy(oxido)phosphaniumyl]-3-(pyridin-2-ylamino)prop-2-enoate
• CAS: 1227779-27-2
• 化学式: C₁₄H₂₁N₂O₅P
• 分子量: 328.305
• InChiKey: QNAPRSBMUUEWCF-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 ethyl 3-methoxy-2-diethoxyphosphorylacrylate 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 16.0h， 生成 (Z)-ethyl 2-(diethoxyphosphoryl)-3-(pyridin-2-ylamino)acrylate 、 (E)-ethyl 2-(diethoxyphosphoryl)-3-(pyridin-2-ylamino)acrylate
  参考文献：
  名称：

  Efficient synthesis of phosphorylated ortho-fused azaheterocycles

  摘要：

  A simple and efficient two-step synthesis of various ortho-fused azaheterocycles, containing phosphorylated pyrimidinones as a parent component, was accomplished by the reaction of 2-diethoxyphosphoryl-3-methoxyacrylate with heteroaromatic amines followed by intramolecular N-acylation of the obtained substitution products. Optimization studies performed for the N-acylation reaction revealed that heating the addition products in Dowtherm A at 250 C gave the best results. The same conditions applied in the intramolecular cyclization of ethyl 2-diethoxyphosphoryl-3-aminophenylacrylate gave expected product of the electrophilic aromatic substitution, but in low yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.139