4-[4-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-butyl]-benzoic acid | 1026616-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 4-[4-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-butyl]-benzoic acid
• 英文别名: 4-[4-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)butyl]benzoic acid
• CAS: 1026616-52-3
• 化学式: C₁₇H₁₉N₅O₂
• 分子量: 325.37
• InChiKey: LRDSECLIENYITE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  131
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[4-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-butyl]-benzoic acid 在 sodium hydroxide 、 氰基磷酸二乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-{4-[4-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-butyl]-benzoylamino}-pentanedioic acid
  参考文献：
  名称：

  A novel synthetic approach to pyrrolo[2,3-d]pyrimidine antifolates

  摘要：

  A novel and efficient synthetic method for the synthesis of pyrrolo[2,3-d]pyrimidine antifolates is described. The key reaction of this method is the photo-initiated free radical addition of bromomalononitrile or ethyl bromocyanoacetate to an enol ether to afford the backbone skeleton of the targeted antifolate molecule. The key intermediates 3 or 4 are smoothly converted to the pyrrolo[2,3-d]pyrimidine antifolates 1 or 2 in three steps and in high overall yield.

  DOI：

  10.1021/jo00059a016
• 作为产物：
  描述：

  Tert-butyl 4-[6,6-dimethoxy-5-(2,4,6-triaminopyrimidin-5-yl)hexyl]benzoate 在 水 、 三氟乙酸 作用下， 生成 4-[4-(2,4-Diamino-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-butyl]-benzoic acid
  参考文献：
  名称：

  A novel synthetic approach to pyrrolo[2,3-d]pyrimidine antifolates

  摘要：

  A novel and efficient synthetic method for the synthesis of pyrrolo[2,3-d]pyrimidine antifolates is described. The key reaction of this method is the photo-initiated free radical addition of bromomalononitrile or ethyl bromocyanoacetate to an enol ether to afford the backbone skeleton of the targeted antifolate molecule. The key intermediates 3 or 4 are smoothly converted to the pyrrolo[2,3-d]pyrimidine antifolates 1 or 2 in three steps and in high overall yield.

  DOI：

  10.1021/jo00059a016

文献信息

• A novel synthetic approach to pyrrolo[2,3-d]pyrimidine antifolates
  作者：Tetsuo Miwa、Takenori Hitaka、Hiroshi Akimoto

  DOI：10.1021/jo00059a016

  日期：1993.3

  A novel and efficient synthetic method for the synthesis of pyrrolo[2,3-d]pyrimidine antifolates is described. The key reaction of this method is the photo-initiated free radical addition of bromomalononitrile or ethyl bromocyanoacetate to an enol ether to afford the backbone skeleton of the targeted antifolate molecule. The key intermediates 3 or 4 are smoothly converted to the pyrrolo[2,3-d]pyrimidine antifolates 1 or 2 in three steps and in high overall yield.