4-methoxyphenyl 2-(methylamino)ethyl carbonate hydrochloride | 123183-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxyphenyl 2-(methylamino)ethyl carbonate hydrochloride
• 英文别名: (4-Methoxyphenyl) 2-(methylamino)ethyl carbonate;hydrochloride
• CAS: 123183-71-1
• 化学式: C₁₁H₁₅NO₄*ClH
• 分子量: 261.705
• InChiKey: QHUMMTZFJGIRRE-UHFFFAOYSA-N

物化性质

• 沸点：
  342.2±42.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Carbonic acid 2-(tert-butoxycarbonyl-methyl-amino)-ethyl ester 4-methoxy-phenyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以61%的产率得到4-methoxyphenyl 2-(methylamino)ethyl carbonate hydrochloride
  参考文献：
  名称：

  Cyclization-activated prodrugs. Basic carbamates of 4-hydroxyanisole

  摘要：

  A series of basic carbamates of 4-hydroxyanisole was prepared and evaluated as progenitors of this melanocytotoxic phenol. All of the carbamates were relatively stable at low pH but released 4-hydroxyanisole cleanly at pH 7.4 at rates that were structure dependent. A detailed study of the N-methyl-N-[2-(methylamino)ethyl]carbamate showed that generation of the parent phenol followed first-order kinetics with t1/2 = 36.3 min at pH 7.4, 37 degrees C, and was accompanied by formation of N,N'-dimethylimidazolidinone. These basic carbamates are examples of cyclization-activated prodrugs in which generation of the active drug is not linked to enzymatic cleavage but rather depends solely upon a predictable, intramolecular cyclization-elimination reaction.

  DOI：

  10.1021/jm00163a016

文献信息

• Cyclization-activated prodrugs. Basic carbamates of 4-hydroxyanisole
  作者：Walfred S. Saari、John E. Schwering、Paulette A. Lyle、Steven J. Smith、Edward L. Engelhardt

  DOI：10.1021/jm00163a016

  日期：1990.1

  A series of basic carbamates of 4-hydroxyanisole was prepared and evaluated as progenitors of this melanocytotoxic phenol. All of the carbamates were relatively stable at low pH but released 4-hydroxyanisole cleanly at pH 7.4 at rates that were structure dependent. A detailed study of the N-methyl-N-[2-(methylamino)ethyl]carbamate showed that generation of the parent phenol followed first-order kinetics with t1/2 = 36.3 min at pH 7.4, 37 degrees C, and was accompanied by formation of N,N'-dimethylimidazolidinone. These basic carbamates are examples of cyclization-activated prodrugs in which generation of the active drug is not linked to enzymatic cleavage but rather depends solely upon a predictable, intramolecular cyclization-elimination reaction.