3-(苄氧基)环磷酰胺 | 78336-01-3

• 中文名称: 3-(苄氧基)环磷酰胺
• 英文名称: 3-(benzyloxy)cyclophosphamide
• CAS: 78336-01-3
• 化学式: C₁₄H₂₁Cl₂N₂O₃P
• 分子量: 367.212
• InChiKey: ABZIGTOFONSWCL-UHFFFAOYSA-N

物化性质

• 沸点：
  450.5±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  42.01
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(苄氧基)环磷酰胺 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 25.0~50.0 ℃ 、310.27 kPa 条件下， 反应 73.0h， 生成
  参考文献：
  名称：

  Synthesis of 3-hydroxycyclophosphamide and studies related to its possible role in the metabolism of cyclophosphamide

  摘要：

  Hydrogenolysis of 3-(benzyloxy)cyclophosphamide (10) using Pd/C catalyst and ethyl acetate as solvent leads to the formation of 3-hydroxycyclophosphamide (3, approximately 20%) and cyclophosphamide (1, approximately 10%), accompanied by regioselective hydrogen-exchange reactions at the C-4 and C-5 positions in 3 and 1. A variety of oxidizing reagents and liver microsomal incubation failed to provide evidence (31P NMR) for conversion of 1 into 3, whereas identical incubation of 3 led to its reduction to 1. Compound 3 is stable at pH 6.5-8.2, 37 degrees C, and exhibits anticancer activity comparable to 1 when tested against L1210 leukemia in mice. Data are discussed with regard to a previously reported suggestion that metabolism of 1 may involved oxidation to give 3 followed by rearrangement of 3 to 2.

  DOI：

  10.1021/jm00144a007
• 作为产物：
  描述：

  O-苄基羟胺 在 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 188.0h， 生成 3-(苄氧基)环磷酰胺
  参考文献：
  名称：

  Synthesis of 3-hydroxycyclophosphamide and studies related to its possible role in the metabolism of cyclophosphamide

  摘要：

  Hydrogenolysis of 3-(benzyloxy)cyclophosphamide (10) using Pd/C catalyst and ethyl acetate as solvent leads to the formation of 3-hydroxycyclophosphamide (3, approximately 20%) and cyclophosphamide (1, approximately 10%), accompanied by regioselective hydrogen-exchange reactions at the C-4 and C-5 positions in 3 and 1. A variety of oxidizing reagents and liver microsomal incubation failed to provide evidence (31P NMR) for conversion of 1 into 3, whereas identical incubation of 3 led to its reduction to 1. Compound 3 is stable at pH 6.5-8.2, 37 degrees C, and exhibits anticancer activity comparable to 1 when tested against L1210 leukemia in mice. Data are discussed with regard to a previously reported suggestion that metabolism of 1 may involved oxidation to give 3 followed by rearrangement of 3 to 2.

  DOI：

  10.1021/jm00144a007