(4-乙酰氨基苯基)丁基碳酸酯 | 19872-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-乙酰氨基苯基)丁基碳酸酯
• 英文名称: 4-butyloxycarbonyloxyacetanilide
• 英文别名: 1-acetylamino-4-butoxycarbonyloxy-benzene；(4-Acetamino-phenyl)-kohlensaeure-butylester；1-Acetylamino-4-butoxycarbonyloxy-benzol；4-Acetaminophenyl-butylcarbonat；4-Acetamidophenyl butyl carbonate；(4-acetamidophenyl) butyl carbonate
• CAS: 19872-68-5
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: HMDOTBHCMSTMJG-UHFFFAOYSA-N

物化性质

• 熔点：
  119.75°C
• 沸点：
  394.43°C (rough estimate)
• 密度：
  1.1667 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对乙酰氨基酚 、 氯甲酸丁酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以63%的产率得到(4-乙酰氨基苯基)丁基碳酸酯
  参考文献：
  名称：

  Topical Delivery of a Model Phenolic Drug: Alkyloxycarbonyl Prodrugs of Acetaminophen

  摘要：

  Purpose. To determine whether the delivery of a phenolic parent drug by its alkyloxycarbonyl (AOC) prodrugs through hairless mouse skin would show similar dependencies on water and lipid solubilities that similar prodrugs of more polar heterocyclic amide and imide parent drugs have shown.Methods. Flux through hairless mouse skin from suspensions in isopropyl myristate (J(MIPM)), solubilities in IPM (S-IPM) and water (S-AQ), and partition coefficients between isopropyl myristate (IPM) and pH 4.0 buffer (K-IPM:4.0) were measured for two series of AOC derivatives of acetaminophen ( APAP); their solubilities in pH 4.0 buffer (S-4.0) were estimated from S-IPM/K-IPM:4.0. Log J(MIPM) values were calculated from the n = 43 coefficients for the parameters in the transformed Potts-Guy (Roberts-Sloan) equation, and the average error of prediction (Delta log J'(IPM)) was calculated. The J(MIPM), S-IPM, S-4.0, and molecular weight ( MW) data for this series and two other series were combined with the n = 43 database to give a n = 61 database, and new best fit coefficients were determined for the Roberts-Sloan equation: log J(MIPM) = x + y log S-IPM + (1 - y) log S-4.0 - z MW.Results. All of the 4-AOC-APAP derivatives underperformed based on their predicted log J(MIPM) (Delta log J'(MIPM) = 0.275 +/- 0.147 log units) and, although the two more water soluble members of this more lipid soluble series were more effective than APAP, they were only marginally so: <2 times. Addition of three new series to the n = 43 database for the Roberts-Sloan equation did not substantially change the coefficients to the parameters: x, y, z, and r(2) = -0.322, 0.530, 0.00337 and 0.92, respectively.Conclusions. The topical delivery of a model phenolic drug by its AOC prodrugs through hairless mouse skin from IPM shows the same dependence on S-IPM, S-4.0, and MW as the delivery of polar heterocycles by their similar prodrugs.

  DOI：

  10.1023/b:pham.0000029281.12753.25

文献信息

• Regioselective synthesis of 2,4,6-triaminopyridines
  作者：Rupa Shetty、Duyan Nguyen、Dietmar Flubacher、Franziska Ruggle、Andreas Schumacher、Martha Kelly、Enrique Michelotti

  DOI：10.1016/j.tetlet.2006.10.159

  日期：2007.1

  A regioselective synthesis of 2,4,6-trisubstituted pyridine is described starting from 2,6-dibromo-4-nitropyridine. All three different regioisomers of the 2,4,6-triamino substituted pyridine have been synthesized in four to five steps. The method described is a general route to unsymmetrical 2,4,6-trisubstituted amino pyridines. (c) 2006 Elsevier Ltd. All rights reserved.
• Topical Delivery of a Model Phenolic Drug: Alkyloxycarbonyl Prodrugs of Acetaminophen
  作者：Scott C. Wasdo、Kenneth B. Sloan

  DOI：10.1023/b:pham.0000029281.12753.25

  日期：2004.6

  Purpose. To determine whether the delivery of a phenolic parent drug by its alkyloxycarbonyl (AOC) prodrugs through hairless mouse skin would show similar dependencies on water and lipid solubilities that similar prodrugs of more polar heterocyclic amide and imide parent drugs have shown.Methods. Flux through hairless mouse skin from suspensions in isopropyl myristate (J(MIPM)), solubilities in IPM (S-IPM) and water (S-AQ), and partition coefficients between isopropyl myristate (IPM) and pH 4.0 buffer (K-IPM:4.0) were measured for two series of AOC derivatives of acetaminophen ( APAP); their solubilities in pH 4.0 buffer (S-4.0) were estimated from S-IPM/K-IPM:4.0. Log J(MIPM) values were calculated from the n = 43 coefficients for the parameters in the transformed Potts-Guy (Roberts-Sloan) equation, and the average error of prediction (Delta log J'(IPM)) was calculated. The J(MIPM), S-IPM, S-4.0, and molecular weight ( MW) data for this series and two other series were combined with the n = 43 database to give a n = 61 database, and new best fit coefficients were determined for the Roberts-Sloan equation: log J(MIPM) = x + y log S-IPM + (1 - y) log S-4.0 - z MW.Results. All of the 4-AOC-APAP derivatives underperformed based on their predicted log J(MIPM) (Delta log J'(MIPM) = 0.275 +/- 0.147 log units) and, although the two more water soluble members of this more lipid soluble series were more effective than APAP, they were only marginally so: <2 times. Addition of three new series to the n = 43 database for the Roberts-Sloan equation did not substantially change the coefficients to the parameters: x, y, z, and r(2) = -0.322, 0.530, 0.00337 and 0.92, respectively.Conclusions. The topical delivery of a model phenolic drug by its AOC prodrugs through hairless mouse skin from IPM shows the same dependence on S-IPM, S-4.0, and MW as the delivery of polar heterocycles by their similar prodrugs.