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.
• Degradation Products of Cyclophosphamide Synthesis and Structural studies
  作者：Ulf Niemeyer、Bernhard Kutscher、Jürgen Engel、Ion Neda、Axel Fischer、Reinhard Schmutzler、Peter G. Jones、Marie-C. Malet-Martino、Véronique Gilard、Robert Martino

  DOI：10.1080/10426509608545193

  日期：1996.1

  cyclophosphamide, heated up to its melting point, the first pathway predominates over the second one. The structures of the phosphorus compounds were established by 1H and 31P NMR spectroscopy, and synthesis. The structure of the bicyclic compound 2 is confirmed by a single crystal X-ray diffraction study which allows an explanation for the selective and immediate hydrolysis with formation of a nine-membered

  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。