tetraethyl {[(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-amino]-methylene}bisphosphonate | 1407522-81-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: tetraethyl {[(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-amino]-methylene}bisphosphonate
• 英文别名: 5-[Bis(diethoxyphosphoryl)methylamino]-1,3-dimethylpyrimidine-2,4-dione；5-[bis(diethoxyphosphoryl)methylamino]-1,3-dimethylpyrimidine-2,4-dione
• CAS: 1407522-81-9
• 化学式: C₁₅H₂₉N₃O₈P₂
• 分子量: 441.358
• InChiKey: ZVDUEXIDRVCRAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-氨基-1,3-二甲基嘧啶-2,4(1H,3H)-二酮 、 二乙基亚磷酸氢酯 、 原甲酸三乙酯 在 sodium 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以72.8%的产率得到tetraethyl {[(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-amino]-methylene}bisphosphonate
  参考文献：
  名称：

  Synthesis, Quantitative Structure–Activity Relationship, and Anti-Inflammatory Profiles of Substituted 5- and 6-N-Heterocycle Bisphosphonate Esters

  摘要：

  A modified multicomponent reaction in a one-pot synthesis of a new series of substituted N-heterocyclic aminomethylene bisphosphonates, in high rates, was described. Accordingly, synthesis of alpha-aminobisphosphonates was achieved, via the Kabachnik-Fields reaction, from the substituted amine with triethyl orthoformate, and followed by treating the product mixture with a toluene solution containing diethyl phosphite-sodium salt. The design of potentially anti-inflammatory bisphosphonates (BPs) relied on the results of computer-assisted molecular modeling. If Later, new BPs were evaluated in animal model of chronic inflammation using the delayed-type hypersensitivity granuloma reaction.

  DOI：

  10.1080/00397911.2011.595603

文献信息

• Synthesis, Quantitative Structure–Activity Relationship, and Anti-Inflammatory Profiles of Substituted 5- and 6-<i>N</i>-Heterocycle Bisphosphonate Esters
  作者：Abeer A. Shaddy、Azza A. Kamel、Wafaa M. Abdou

  DOI：10.1080/00397911.2011.595603

  日期：2013.1

  A modified multicomponent reaction in a one-pot synthesis of a new series of substituted N-heterocyclic aminomethylene bisphosphonates, in high rates, was described. Accordingly, synthesis of alpha-aminobisphosphonates was achieved, via the Kabachnik-Fields reaction, from the substituted amine with triethyl orthoformate, and followed by treating the product mixture with a toluene solution containing diethyl phosphite-sodium salt. The design of potentially anti-inflammatory bisphosphonates (BPs) relied on the results of computer-assisted molecular modeling. If Later, new BPs were evaluated in animal model of chronic inflammation using the delayed-type hypersensitivity granuloma reaction.