Acetic acid 1-acetoxy-3-(chloro-methoxy-phosphoryloxy)-propyl ester | 123824-15-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: Acetic acid 1-acetoxy-3-(chloro-methoxy-phosphoryloxy)-propyl ester
• CAS: 123824-15-7
• 化学式: C₈H₁₄ClO₇P
• 分子量: 288.622
• InChiKey: NJRLHFBHXXLOKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  二(2-氯乙基)胺盐酸盐 、 Acetic acid 1-acetoxy-3-(chloro-methoxy-phosphoryloxy)-propyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以0.51 g的产率得到3,3-diacetoxypropyl methyl N,N-bis(2-chloroethyl)phosphoramidate
  参考文献：
  名称：

  Aldophosphamide acetal diacetate and structural analogs: synthesis and cytotoxicity studies

  摘要：

  The synthesis of aldophosphamide acetal diacetate and a number of structural analogues is described. These compounds are designed to undergo biotransformation to the corresponding aldehydes in the presence of carboxylate esterases, enzymes that are ubiquitous in mammalian tissue. Several of these aldehydes can theoretically exist in pseudoequilibrium with the 4-hydroxyoxazaphosphorine tautomers; others lack this capability. The half-lives of the acetals in 0.05 M phosphate buffer, pH 7.4, at 37-degrees-C ranged from 1 to 2 days. In the presence of 2 unit equiv of porcine liver carboxylate esterase, all of the compounds were hydrolyzed with half-lives of less than 1 min. Although closely structurally related, the compounds exhibited a wide range of cytotoxicities to L1210 murine leukemia cells in vitro.

  DOI：

  10.1021/jm00105a030
• 作为产物：
  描述：

  甲醇 、 2,2,8-trimethyl-6-(2-methylallyl)-2l5-nona-1,8-diene 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 Acetic acid 1-acetoxy-3-(chloro-methoxy-phosphoryloxy)-propyl ester
  参考文献：
  名称：

  Aldophosphamide acetal diacetate and structural analogs: synthesis and cytotoxicity studies

  摘要：

  The synthesis of aldophosphamide acetal diacetate and a number of structural analogues is described. These compounds are designed to undergo biotransformation to the corresponding aldehydes in the presence of carboxylate esterases, enzymes that are ubiquitous in mammalian tissue. Several of these aldehydes can theoretically exist in pseudoequilibrium with the 4-hydroxyoxazaphosphorine tautomers; others lack this capability. The half-lives of the acetals in 0.05 M phosphate buffer, pH 7.4, at 37-degrees-C ranged from 1 to 2 days. In the presence of 2 unit equiv of porcine liver carboxylate esterase, all of the compounds were hydrolyzed with half-lives of less than 1 min. Although closely structurally related, the compounds exhibited a wide range of cytotoxicities to L1210 murine leukemia cells in vitro.

  DOI：

  10.1021/jm00105a030