N,N-二(2-氯乙基)四氢-3-(2,2,6,6-四甲基-4-哌啶基)-2H-1,3,2-氧杂氮杂磷杂苯-2-胺2-氧化物 | 82576-63-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N,N-二(2-氯乙基)四氢-3-(2,2,6,6-四甲基-4-哌啶基)-2H-1,3,2-氧杂氮杂磷杂苯-2-胺2-氧化物
• 英文名称: N,N-bis(2-chloroethyl)-3-(2,2,6,6-tetramethyl-4-piperidinyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide
• 英文别名: N,N-bis(2-chloroethyl)-2-oxo-3-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,2lambda5-oxazaphosphinan-2-amine；N,N-bis(2-chloroethyl)-2-oxo-3-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,2λ5-oxazaphosphinan-2-amine
• CAS: 82576-63-4
• 化学式: C₁₆H₃₂Cl₂N₃O₂P
• 分子量: 400.329
• InChiKey: YODYWNKJLGXFMH-UHFFFAOYSA-N

物化性质

• 沸点：
  457.1±55.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-二(2-氯乙基)四氢-3-(2,2,6,6-四甲基-4-哌啶基)-2H-1,3,2-氧杂氮杂磷杂苯-2-胺2-氧化物 在 sodium tungstate 、 双氧水 作用下， 以 水 为溶剂， 反应 96.0h， 以36%的产率得到4-(2-(二(2-氯乙基)氨基)二氢-2H-1,3,2-氧杂氮杂磷杂苯-3(4H)-基)-2,2,6,6-四甲基-1-哌啶基氧基 P-氧化物
  参考文献：
  名称：

  Synthesis and study of a spin-labeled cyclophosphamide analog 3-(1-oxy-2,2,6,6-tetramethyl-4-piperidinyl)cyclophosphamide

  摘要：

  3-(1-Oxy-2,2,6,6-tetramethyl-4-piperidinyl)cyclophosphamide (7) was isolated in 36% yield following H2O2-Na2WO4 oxidation of 3-(2,2,6,6-tetramethyl-4-piperidinyl)cyclophosphamide (6), which was synthesized in three steps (25% yield) starting with 4-amino-2,2,6,6-tetramethylpiperidine. Binding of 7 to mouse liver microsomes was investigated by optical and electron spin resonance spectroscopy. Compared with the mouse liver microsomal metabolism of 1, separate incubations of 6 and an ca. 1:1 mixture of 1 and 6 gave approximately 90 and 60% less acrolein, respectively. A spin-labeled metabolite of 7, viz., N-(1-oxy-2,2,6,6-tetramethyl-4-piperidinyl)phosphoramide mustard (9), was synthesized and its intramolecular O-alkylation at pH 7.4, 37 degrees C, was studied by 31P NMR spectroscopy. Compounds 7 and 9 were inactive in screening tests against L1210 lymphoid leukemia in mice.

  DOI：

  10.1021/jm00351a021
• 作为产物：
  描述：

  2,2,6,6-四甲基哌啶胺 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 为溶剂， 反应 73.5h， 生成 N,N-二(2-氯乙基)四氢-3-(2,2,6,6-四甲基-4-哌啶基)-2H-1,3,2-氧杂氮杂磷杂苯-2-胺2-氧化物
  参考文献：
  名称：

  Synthesis and study of a spin-labeled cyclophosphamide analog 3-(1-oxy-2,2,6,6-tetramethyl-4-piperidinyl)cyclophosphamide

  摘要：

  3-(1-Oxy-2,2,6,6-tetramethyl-4-piperidinyl)cyclophosphamide (7) was isolated in 36% yield following H2O2-Na2WO4 oxidation of 3-(2,2,6,6-tetramethyl-4-piperidinyl)cyclophosphamide (6), which was synthesized in three steps (25% yield) starting with 4-amino-2,2,6,6-tetramethylpiperidine. Binding of 7 to mouse liver microsomes was investigated by optical and electron spin resonance spectroscopy. Compared with the mouse liver microsomal metabolism of 1, separate incubations of 6 and an ca. 1:1 mixture of 1 and 6 gave approximately 90 and 60% less acrolein, respectively. A spin-labeled metabolite of 7, viz., N-(1-oxy-2,2,6,6-tetramethyl-4-piperidinyl)phosphoramide mustard (9), was synthesized and its intramolecular O-alkylation at pH 7.4, 37 degrees C, was studied by 31P NMR spectroscopy. Compounds 7 and 9 were inactive in screening tests against L1210 lymphoid leukemia in mice.

  DOI：

  10.1021/jm00351a021

文献信息

• Synthesis and study of a spin-labeled cyclophosphamide analog 3-(1-oxy-2,2,6,6-tetramethyl-4-piperidinyl)cyclophosphamide
  作者：Fai Po Tsui、Frank A. Robey、Thomas W. Engle、Susan Marie Ludeman、Gerald Zon

  DOI：10.1021/jm00351a021

  日期：1982.9

  3-(1-Oxy-2,2,6,6-tetramethyl-4-piperidinyl)cyclophosphamide (7) was isolated in 36% yield following H2O2-Na2WO4 oxidation of 3-(2,2,6,6-tetramethyl-4-piperidinyl)cyclophosphamide (6), which was synthesized in three steps (25% yield) starting with 4-amino-2,2,6,6-tetramethylpiperidine. Binding of 7 to mouse liver microsomes was investigated by optical and electron spin resonance spectroscopy. Compared with the mouse liver microsomal metabolism of 1, separate incubations of 6 and an ca. 1:1 mixture of 1 and 6 gave approximately 90 and 60% less acrolein, respectively. A spin-labeled metabolite of 7, viz., N-(1-oxy-2,2,6,6-tetramethyl-4-piperidinyl)phosphoramide mustard (9), was synthesized and its intramolecular O-alkylation at pH 7.4, 37 degrees C, was studied by 31P NMR spectroscopy. Compounds 7 and 9 were inactive in screening tests against L1210 lymphoid leukemia in mice.