diethyl 5-amino-3-((diethoxyphosphoryl)methyl)thiophene-2,4-dicarboxylate | 1315306-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: diethyl 5-amino-3-((diethoxyphosphoryl)methyl)thiophene-2,4-dicarboxylate
• CAS: 1315306-43-4
• 化学式: C₁₅H₂₄NO₇PS
• 分子量: 393.398
• InChiKey: HLUPSRBMOYOFSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  25.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  114.15
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  ethyl 4-diethoxyphosphoryl-3-oxobutanoate 在 ammonium acetate 、 sodium hydride 、 sulfur 、 溶剂黄146 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 24.0h， 生成 diethyl 5-amino-3-((diethoxyphosphoryl)methyl)thiophene-2,4-dicarboxylate
  参考文献：
  名称：

  Novel aminophosphonothiophene derivatives from β-keto-δ-carbethoxyphosphonates and phosphineoxides

  摘要：

  The reaction of -keto--carbethoxyphosphonates and phosphineoxides with active methylene nitriles leads to the corresponding phosphonoalkylidenes. Treatment of these compounds with sulfur, under the classical Gewald reaction conditions, gives a ca. 1:1 mixture of novel aminophosphonothiophene derivatives 3 and 3'. In order to improve the regioselectivity of the reaction, novel conditions have been developed for the Gewald condensation, in which we used an inorganic base NaH in THF as the solvent. These conditions afforded exclusively the 3-regioisomer in good yield. [image omitted].

  DOI：

  10.1080/17415993.2011.570763