克罗拉滨杂质7 | 1140251-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 中文名称: 克罗拉滨杂质7
• 中文别名: 克罗拉滨杂质17；氯法拉滨相关化合物
• 英文名称: N-(6-amino-2-chloro-4-((2S,3S,4R,5R)-3-fluoro-4,5-dihydroxytetrahydro-2H-pyran-2-ylamino)pyrimidin-5-yl)formamide
• 英文别名: N-[4-Amino-2-chloro-6-[(2-deoxy-2-fluoro-alpha-D-arabinopyranosyl)amino]-5-pyrimidinyl]-formamide；N-[4-amino-2-chloro-6-[[(2S,3S,4R,5R)-3-fluoro-4,5-dihydroxyoxan-2-yl]amino]pyrimidin-5-yl]formamide
• CAS: 1140251-30-4
• 化学式: C₁₀H₁₃ClFN₅O₄
• 分子量: 321.696
• InChiKey: GIFVSTNLGMIVGT-AQZRFWRFSA-N

物化性质

• 熔点：
  >178°C (dec.)
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  143
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  克罗拉滨杂质7 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 N-(6-amino-2-chloro-4-((2R,3S,4R,5R)-3-fluoro-4,5-dihydroxytetrahydro-2H-pyran-2-ylamino)pyrimidin-5-yl)formamide
  参考文献：
  名称：

  Synthetic Studies on Formamidopyrimidines Related to Clofarabine

  摘要：

  Degradation of clofarabine (3) in 0.9% saline solution at 100C afforded three degradation products which were determined to be formamidopyrimidines 4-6.Compounds 4 and 5 were assigned as C(1)' anomers on the basis of one-dimensional and two-dimensional NMR experiments, whereas 6 was found to be the formamidopyrimidine lacking the sugar moiety. An improved procedure for the synthesis of formamidopyrimidines was developed, wherein benzoylated clofarabine (11) was treated with allyl chloroformate, followed by deprotection of the alloc group with catalytic Pd(PPh(3))(4) and dimedone. A synthesis of compound 6 from 4 is also described.

  DOI：

  10.1080/15257770802257770
• 作为产物：
  描述：

  克罗拉滨 在 sodium hydroxide 、 sodium dihydrogenphosphate 、 sodium chloride 作用下， 以 水 为溶剂， 反应 19.0h， 以24.9 mg的产率得到克罗拉滨杂质7
  参考文献：
  名称：

  Synthetic Studies on Formamidopyrimidines Related to Clofarabine

  摘要：

  Degradation of clofarabine (3) in 0.9% saline solution at 100C afforded three degradation products which were determined to be formamidopyrimidines 4-6.Compounds 4 and 5 were assigned as C(1)' anomers on the basis of one-dimensional and two-dimensional NMR experiments, whereas 6 was found to be the formamidopyrimidine lacking the sugar moiety. An improved procedure for the synthesis of formamidopyrimidines was developed, wherein benzoylated clofarabine (11) was treated with allyl chloroformate, followed by deprotection of the alloc group with catalytic Pd(PPh(3))(4) and dimedone. A synthesis of compound 6 from 4 is also described.

  DOI：

  10.1080/15257770802257770