N-(2-氯乙基)-N'-(3-磷酰丙基)乙二胺

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 中文名称: N-(2-氯乙基)-N'-(3-磷酰丙基)乙二胺
• 英文名称: 1-propanol 3-<<2-<(2-chloroethyl)amino>ethyl>amino> dihydrogen phosphate dihydrochloride
• 英文别名: 3-[2-(2-chloroethylamino)ethylamino]propyl dihydrogen phosphate;hydron;chloride
• 化学式: C₇H₁₈ClN₂O₄P*2ClH
• 分子量: 333.58
• InChiKey: LUASBHXEWCQULV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.8
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  环磷酰胺 在 盐酸 、 水 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2-氯乙基)-N'-(3-磷酰丙基)乙二胺
  参考文献：
  名称：

  环磷酰胺合成和结构研究的降解产物

  摘要：

  摘要 环磷酰胺在中性或微酸性水溶液中的降解开始于分子内烷基化，导致中间双环化合物立即水解为九元杂环。随后酸催化的 PN 键水解产生磷酸单酯。在强酸性溶液 (1 N HCl) 中，环磷酰胺仅分解为双 (2-氯乙基)-胺和相应的磷酸单酯 H2N(CH2)3OP(O)(OH)2。在加热到熔点的环磷酰胺固体样品中，第一种途径比第二种途径占优势。磷化合物的结构通过 1H 和 31P NMR 光谱和合成确定。

  DOI：

  10.1080/10426509608545193

文献信息

• Chemical and Biological Evaluation of Hydrolysis Products of Cyclophosphamide
  作者：Veronique Gilard、Robert Martino、Marie-C. Malet-Martino、Bernhard Kutscher、Arndt Mueller、Ulf Niemeyer、Joerg Pohl、Emmanuel E. Polymeropoulos

  DOI：10.1021/jm00049a018

  日期：1994.11

  P-31 NMR spectroscopy was used to study the products of the decomposition of cyclophosphamide (1) in buffered solutions at pH's ranging between 1.2 and 8.6 at 20 degrees C and at pH 7.4 at 37 degrees C. At pH 1.2, 1 undergoes a rapid breakdown (t(1/2) = 1.4 days) of the two P-N bonds, giving compounds 2 [HN(CH2CH2Cl)(2)] and 3 [H2N(CH2)(3)OP(O)(OH)(2)] as hydrochlorides. No intermediates were detected. At pH's between 5.4 and 8.6, hydrolysis of 1 during 17 days leads to the sole and previously unknown nine-membered ring compound 13. 13 results from the intramolecular alkylation of 1 giving the bicyclic compound 7 followed by the exothermal hydrolytic breakdown of the P-N bond of its six-membered ring. At pH 2.2 and 3.4, the two hydrolytic pathways coexist since, beside compounds 2 and 3, the hydrochloride of compound 9 [Cl(CH2)(2)NH(CH2)(2)NH(CH2)(3)OP(O)(OH)(2)] is formed, resulting from the acid-catalyzed breakdown of the P-N bond in the nine-membered ring compound 13. At pH 2.2, the presence of chloride ion affected neither the stability of 1 nor the contribution of the two competing hydrolytic pathways. At pH's ranging from 3.4 to 8.6, there is little degradation of 1 since more than 95% of initial 1 was still present after 7 days at 20 degrees C. Under physiological conditions (pH 7.4, 37 degrees C) after 6 days, 45% of 1 is hydrolyzed (t(1/2) = 6.6 days), leading essentially (30% of initial 1) to the nine-membered ring compound 13. The rate of hydrolysis of 13 and the nature of its hydrolysis products were found to depend on pH over the range 0-8.6. After a single ip injection to mice, compounds 3, 9, and 13 were less toxic than 1. They did not exhibit any direct cytotoxic efficacy on the colony-forming capacity of L1210 cells in vitro, and they had no antitumor activity in vivo against P388 leukemia.