benzyl N,N-bis(2-chloroethyl)-N'-(2,2,6,6-tetramethyl-4-piperidinyl)phosphorodiamidate | 82576-67-8

• 英文名称: benzyl N,N-bis(2-chloroethyl)-N'-(2,2,6,6-tetramethyl-4-piperidinyl)phosphorodiamidate
• CAS: 82576-67-8
• 化学式: C₂₀H₃₄Cl₂N₃O₂P
• 分子量: 450.389
• InChiKey: SJCZRCDLMYFNAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  53.6
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  benzyl N,N-bis(2-chloroethyl)-N'-(2,2,6,6-tetramethyl-4-piperidinyl)phosphorodiamidate 在 palladium on activated charcoal sodium tungstate 、 氢气 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 168.5h， 生成 N,N-bis(2-chloroethyl)-N'-(1-oxy-2,2,6,6-tetramethyl-4-piperidinyl)phosphorodiamidic acid
  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：

  苯甲醇钠 在 sodium hydroxide 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 benzyl N,N-bis(2-chloroethyl)-N'-(2,2,6,6-tetramethyl-4-piperidinyl)phosphorodiamidate
  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