2-氨基乙基甲基磷酸酯 | 4275-95-0

• 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: 2-氨基乙基甲基磷酸酯
• 英文名称: 2-Aminoethyl methyl phosphate
• 英文别名: Ethanolamin-phosphorsaeure-methylester；Phosphorsaeure-(2-amino-aethylester)-methylester；Methyl phosphoethanolamine；2-aminoethyl methyl hydrogen phosphate
• CAS: 4275-95-0
• 化学式: C₃H₁₀NO₄P
• 分子量: 155.09
• InChiKey: RHZOTNIARPBHQF-UHFFFAOYSA-N

物化性质

• 熔点：
  199-204 °C
• 沸点：
  244.8±42.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基乙基甲基磷酸酯 、 O-甲基异脲 在 sodium hydroxide 作用下， 以87%的产率得到opheline
  参考文献：
  名称：

  Euerby, Melvin R.; Partridge, Lynda Z.; Gibbons, William A., Journal of Chemical Research, Miniprint, 1988, # 12, p. 3028 - 3051

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Methoxy-2-oxo-1,3,2-oxazaphospholidine 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-氨基乙基甲基磷酸酯
  参考文献：
  名称：

  Euerby, Melvin R.; Partridge, Lynda Z.; Learmonth, Michele P., Journal of Chemical Research, Miniprint, 1987, # 3, p. 815 - 830

  摘要：

  DOI：

文献信息

• Reactivity of N-Phosphorylated Mustards
  作者：Tomasz A. Modro、Charlotte Le Roux、Huijie Wan、Agnes M. Modro

  DOI：10.1080/10426509608545192

  日期：1996.1

  Abstract Products and mechanisms of the fragmentation of ionic phosphoramidates containing the N-(2-chloroethyl) functionality are discussed.

  摘要 讨论了含有 N-(2-氯乙基) 官能团的离子氨基磷酸酯的裂解产物和机理。
• Euerby, Melvin R.; Partridge, Lynda Z.; Learmonth, Michele P., Journal of Chemical Research, Miniprint, 1987, # 3, p. 815 - 830
  作者：Euerby, Melvin R.、Partridge, Lynda Z.、Learmonth, Michele P.、Ball, Hayden L.、Gibbons, William A.

  DOI：——

  日期：——
• Further Syntheses in the Study of Structure-Activity Relationships of Neuropharmacologically Active Amino Acids
  作者：K. S. Cheah、J. C. Watkins

  DOI：10.1021/jm00330a020

  日期：1965.11
• EUERBY M. R.; PARTRIDGE L. Z.; LEARMONTH M. P.; BALL H. L.; GIBBONS W. A., J. CHEM. RES. SYMP.,(1987) N 3, 74-75
  作者：EUERBY M. R.、 PARTRIDGE L. Z.、 LEARMONTH M. P.、 BALL H. L.、 GIBBONS W. A.

  DOI：——

  日期：——
• Decomposition of N-Phosphorylated Nitrogen Mustards: A Mechanistic Investigation
  作者：Charlotte le Roux、Agnes M. Modro、Tomasz A. Modro

  DOI：10.1021/jo00117a039

  日期：1995.6

  Lithium methyl N-(2-chloroethyl)phosphoramidate (2b) and lithium methyl N,N-bis(2-chloroethyl)phosphoramidate (2c) were prepared as models of N-phosphorylated mustards used in cancer chemotherapy. The decomposition of those substrates in D2O and in D2O-pyridine-d(5) was studied to elucidate the mechanism of their alkylating reactivity. The products of the decomposition and the variation of the proportions of the products with time were determined, and the results led to the following conclusions. Decomposition of substrates of the type 2 can follow three independent pathways: (i) 1,5-cyclization to a 1,3,2-oxazaphospholidine derivative, followed by fast ring opening via the pH-dependent P-O or P-N bond cleavage; (ii) 1,3-cyclization to a N-phosphorylated aziridinium derivative, followed by the nucleophilic opening of the aziridine ring; (iii) fragmentation to metaphosphate and aziridine species, followed by rapid reactions of those intermediates with nucleophiles. The first pathway deactivates the substrate with respect to the alkylating reactivity. Relative contributions of individual pathways to the decomposition are highly sensitive to the detailed structure of the substrate and to the nucleophilic composition of the reaction medium.