phenyl cyclophosphoramidate | 50742-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl cyclophosphoramidate
• 英文别名: 2-phenoxy-1,3,2-oxazaphosphinane 2-oxide；Oxo-2-phenoxy-2-oxazaphosphorinan-1,3,2；N,O-Trimethylen-phosphoramidsaeure-phenylester；2-Phenoxy-1,3,2lambda5-oxazaphosphinane 2-oxide；2-phenoxy-1,3,2λ5-oxazaphosphinane 2-oxide
• CAS: 50742-52-4
• 化学式: C₉H₁₂NO₃P
• 分子量: 213.173
• InChiKey: YZJWXUWNAHCIOB-UHFFFAOYSA-N

物化性质

• 沸点：
  293.4±23.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenyl cyclophosphoramidate 生成 Phosphorsaeure-phenyl-(3-amino-propyl)-ester
  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
• 作为产物：
  描述：

  二氯磷酸苯酯 、 3-氨基-1-丙醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90 %的产率得到phenyl cyclophosphoramidate
  参考文献：
  名称：

  含PO分子的扩环反应

  摘要：

  一系列含PO分子的扩环反应已被开发用于合成中等大小环的环状膦酸酯和膦酰胺酯。与更完善的内酰胺衍生物扩环反应相比，反应性趋势最初似乎是反直觉的，但可以通过考虑分别与 P 和 C 杂原子键合的差异来解释。

  DOI：

  10.1039/d3cc02087h

文献信息

• Synthesis and physiological activity of new organophosphorus pesticides of 1,3,2-oxazaphosphorinane series
  作者：A. E. Shipov、G. K. Genkina、O. I. Artyushin、Z. O. Mndzhoyan、B. E. Gushchin、E. I. Chumakova、S. A. Roslavtseva、O. Yu. Eremina、E. I. Bakanova、Yu. S. Kagan、E. A. Ershova、T. A. Mastryukova、M. I. Kabachnik

  DOI：10.1007/bf00696722

  日期：1995.11

  Methods for the synthesis of 2-aryloxy(arylthio)- and 2-alkoxy(alkylthio)-2-thio(oxo)-1,3,2-oxazaphosphorinanes and theirN-substituted derivatives based on the reactions of the corresponding dichlorophosphates, dichlorothio-, and dithiophosphates with 3-aminopropan-1-ol or its substituted derivatives in the presence of Et3N or aqueous alkali under phase transfer catalysis conditions, as well as by

  基于相应的二氯磷酸盐、二氯硫代-和 2-芳氧基（烷硫基）-2-硫代（氧代）-1,3,2-氧氮杂膦烷及其 N-取代衍生物的合成方法，以及二硫代磷酸盐与 3-氨基丙-1-醇或其取代衍生物在 Et3N 或碱水溶液存在下，在相转移催化条件下，以及通过 2-羟基-2-硫代-1 的四甲基铵盐的反应， 3,2-oxazaphosphorinane 与烷基-和酰基卤化物，2-chloro-2-thio-1,3,2-oxazaphosphorinane 与硫醇钠，以及通过其他方法，被开发出来。获得的化合物表现出高杀线虫活性，但对哺乳动物的毒性低。在这些化合物中发现了一些氯菊酯的活性增效剂。
• β-Lactams. XI. Synthesis of <i>N</i>-phosphorylated mono- and bicyclic β-lactams
  作者：George Just、Denise Dugat、Whi-Yu Liu

  DOI：10.1139/v83-296

  日期：1983.8.1

  Starting from appropriately.substituted monocyclic β-lactam, N-phosphorylated mono- and bicyclic β-lactams have been synthesized.

  从适当替代的单环β-内酰胺出发，已合成了N-磷酸化的单环和双环β-内酰胺。
• 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.
• Introducing a New Class of <i>N-</i>Phosphoryl Ynamides via Cu(I)-Catalyzed Amidations of Alkynyl Bromides
  作者：Kyle A. DeKorver、Mary C. Walton、Troy D. North、Richard P. Hsung

  DOI：10.1021/ol201947b

  日期：2011.9.16

  We describe here the first synthesis of N-phosphoryl ynamides featuring C- and P-chirality via copper(I)-catalyzed amidative cross-couplings between phosphoramidates and phosphordiamidates with alkynyl bromides. Also featured is a tandem aza-Claisen-hetero-[2 + 2] cycloaddition for the synthesis of N-phosphoryl azetidin-2-imines.
• Gilard Veronique, Martino Robert, Malet-Martino Marie-C., Kutscher Bernha+, J. Med. Chem, 37 (1994) N 23, S 3986-3993
  作者：Gilard Veronique, Martino Robert, Malet-Martino Marie-C., Kutscher Bernha+

  DOI：——

  日期：——