benzyl 2-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetate | 136055-89-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl 2-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetate
• 英文别名: benzyl (1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetate；benzyl 2-(1,3-dimethyl-2,6-dioxopurin-7-yl)acetate
• CAS: 136055-89-5
• 化学式: C₁₆H₁₆N₄O₄
• 分子量: 328.327
• InChiKey: BFLNZKUKVYHXGL-UHFFFAOYSA-N

物化性质

• 沸点：
  558.5±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  茶碱 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 benzyl 2-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetate
  参考文献：
  名称：

  N 7-Tosyltheophylline (TsTh): A Highly Efficient Reagent for the One-Pot Synthesis of N 7-Alkyltheophyllines from Alcohols

  摘要：

  A convenient and highly efficient one-pot N-alkylation of theophylline from alcohols via N-7-tosyltheophylline (TsTh) is described. In this protocol, the treatment of primary and/or secondary alcohols with a mixture of TsTh and 1,8-diazabicyclo[5.4.0]undec-7-ene in refluxing acetonitrile affords the corresponding N-7-alkyltheophylline in good to excellent yields; the reaction was optimized for solvent and base. This methodology is highly efficient for various structurally diverse primary and secondary alcohols. A plausible mechanism for the one-pot N-alkylation of theophylline with alcohols via TsTh has been suggested.

  DOI：

  10.1055/s-0033-1341026

文献信息

• Repurposing amine and carboxylic acid building blocks with an automatable esterification reaction
  作者：Andrew McGrath、Rui Zhang、Khadija Shafiq、Tim Cernak

  DOI：10.1039/d2cc05670d

  日期：——

  amines and carboxylic acids that complement the popular amide coupling can significantly expand accessible chemical space if they yield products distinct from the classic R–NHC(O)–R′ amide arrangement. Here we have developed an amine–acid esterification reaction based on pyridinium salt activation of amine C–N bonds to create products of type R–OC(O)–R′ upon reaction with alkyl and aryl carboxylic acids

  结合胺和羧酸的新方法补充了流行的酰胺偶联，如果它们产生的产物不同于经典的 R-NHC(O)-R' 酰胺排列，则可以显着扩展可及的化学空间。在这里，我们开发了一种基于胺 C-N 键的吡啶盐活化的胺-酸酯化反应，在与烷基和芳基羧酸反应时产生 R-OC(O)-R' 类型的产物。正如开源机器人的自动化所证明的那样，该协议是健壮和简便的。