3-(2-Isocyanato-phenyl)-propionic acid allyl ester | 187840-94-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(2-Isocyanato-phenyl)-propionic acid allyl ester
• 英文别名: prop-2-enyl 3-(2-isocyanatophenyl)propanoate
• CAS: 187840-94-4
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: RLLLKSUHQQJXRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.73
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(2-Isocyanato-phenyl)-propionic acid allyl ester 在 吗啉 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Synthesis and biological activity of β-glucuronyl carbamate-based prodrugs of paclitaxel as potential candidates for ADEPT

  摘要：

  The syntheses of prodrugs of paclitaxel, which can be used in ADEPT in order to target paclitaxel towards tumor cells, are described. The prodrugs 1 and 2a,b consist of a spacer molecule connected via a carbamate linkage to a beta-glucuronic acid. The spacer molecule is also connected via an ester linkage to the 2'-OH of paclitaxel. Enzyme-catalyzed hydrolysis of the glucuronic acid moiety by human beta-glucuronidase results in the liberation of the parent drug paclitaxel via gamma or delta lactam formation with half-lives of 45 min and 2h (1 and 2h). The prodrugs 1 and 2b are two orders of magnitude less cytotoxic than paclitaxel. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00249-0
• 作为产物：
  描述：

  3-(2-羧基苯基)丙酸 在 4-二甲氨基吡啶 、 二苯基膦叠氮化物 、 三乙胺 、 N,N-二甲基甲酰胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 3-(2-Isocyanato-phenyl)-propionic acid allyl ester
  参考文献：
  名称：

  Synthesis and biological activity of β-glucuronyl carbamate-based prodrugs of paclitaxel as potential candidates for ADEPT

  摘要：

  The syntheses of prodrugs of paclitaxel, which can be used in ADEPT in order to target paclitaxel towards tumor cells, are described. The prodrugs 1 and 2a,b consist of a spacer molecule connected via a carbamate linkage to a beta-glucuronic acid. The spacer molecule is also connected via an ester linkage to the 2'-OH of paclitaxel. Enzyme-catalyzed hydrolysis of the glucuronic acid moiety by human beta-glucuronidase results in the liberation of the parent drug paclitaxel via gamma or delta lactam formation with half-lives of 45 min and 2h (1 and 2h). The prodrugs 1 and 2b are two orders of magnitude less cytotoxic than paclitaxel. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00249-0