5-{N-[4-(4'-chlorophenoxy)but-2-ynyl]-N-ethylamino}-1,3-dimethyluracil | 207112-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-{N-[4-(4'-chlorophenoxy)but-2-ynyl]-N-ethylamino}-1,3-dimethyluracil
• 英文别名: 5-[4-(4-Chlorophenoxy)but-2-ynyl-ethylamino]-1,3-dimethylpyrimidine-2,4-dione
• CAS: 207112-22-9
• 化学式: C₁₈H₂₀ClN₃O₃
• 分子量: 361.828
• InChiKey: DOKXCHZDBSOBFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-{N-[4-(4'-chlorophenoxy)but-2-ynyl]-N-ethylamino}-1,3-dimethyluracil 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 6-[(4-Chlorophenoxy)methyl]-5-ethyl-7-(methoxymethyl)-1,3-dimethylpyrrolo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Studies on Pyrimidine-Annelated Heterocycles:  Synthesis of Pyrrolo[3,2-d]pyrimidines by Amine Oxide Rearrangement

  摘要：

  A number of pyrrolo[3,2-d]pyrimidine derivatives (5a-f) were synthesized in 90-95% yields from the corresponding 5-[N-[4-(aryloxy)but-2-ynyl]-N-ethylamino]-1,3-dimethyluracils 4a-f by simple treatment with 1 equiv of m-chloroperoxybenzoic acid in dichloromethane at 0-5 degrees C for 12-15 h. The resulting benzoates (5a-f) were easily converted to methoxy derivatives 11a-f in 92-94% yields when refluxed in methanol for 20-22 h.

  DOI：

  10.1021/jo9718861
• 作为产物：
  描述：

  5-溴-1,3-二甲基尿嘧啶 在 potassium carbonate 、 sodium iodide 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 5-{N-[4-(4'-chlorophenoxy)but-2-ynyl]-N-ethylamino}-1,3-dimethyluracil
  参考文献：
  名称：

  Studies on Pyrimidine-Annelated Heterocycles:  Synthesis of Pyrrolo[3,2-d]pyrimidines by Amine Oxide Rearrangement

  摘要：

  A number of pyrrolo[3,2-d]pyrimidine derivatives (5a-f) were synthesized in 90-95% yields from the corresponding 5-[N-[4-(aryloxy)but-2-ynyl]-N-ethylamino]-1,3-dimethyluracils 4a-f by simple treatment with 1 equiv of m-chloroperoxybenzoic acid in dichloromethane at 0-5 degrees C for 12-15 h. The resulting benzoates (5a-f) were easily converted to methoxy derivatives 11a-f in 92-94% yields when refluxed in methanol for 20-22 h.

  DOI：

  10.1021/jo9718861

文献信息

• Studies on Pyrimidine-Annelated Heterocycles:  Synthesis of Pyrrolo[3,2-<i>d</i>]pyrimidines by Amine Oxide Rearrangement
  作者：K. C. Majumdar、U. Das、N. K. Jana

  DOI：10.1021/jo9718861

  日期：1998.5.1

  A number of pyrrolo[3,2-d]pyrimidine derivatives (5a-f) were synthesized in 90-95% yields from the corresponding 5-[N-[4-(aryloxy)but-2-ynyl]-N-ethylamino]-1,3-dimethyluracils 4a-f by simple treatment with 1 equiv of m-chloroperoxybenzoic acid in dichloromethane at 0-5 degrees C for 12-15 h. The resulting benzoates (5a-f) were easily converted to methoxy derivatives 11a-f in 92-94% yields when refluxed in methanol for 20-22 h.