[(1S,4R)-4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-cyclopentene-1-yl]methanol | 399508-07-7

• 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: [(1S,4R)-4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-cyclopentene-1-yl]methanol
• 英文别名: (-)-(1S,4R)-4-[4-chloro-7H-pyrrolo(2,3-d)pyrimidin-7-yl]-2-cyclopentene-1-methanol；[(1S,4R)-4-(4-chloropyrrolo[2,3-d]pyrimidin-7-yl)cyclopent-2-en-1-yl]methanol
• CAS: 399508-07-7
• 化学式: C₁₂H₁₂ClN₃O
• 分子量: 249.7
• InChiKey: PLOXOSFGBUBBAN-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1S,4R)-4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-cyclopentene-1-yl]methanol 在 氨 作用下， 反应 72.0h， 以68%的产率得到(-)-(1S,4R)-4-[4-amino-7H-pyrrolo(2,3-d)pyrimidin-7-yl]-2-cyclopentene-1-methanol
  参考文献：
  名称：

  Phosphoramidate Protides of Carbocyclic 2′,3′‐Dideoxy‐2′,3′‐Didehydro‐7‐Deazaadenosine with Potent Activity Against HIV and HBV

  摘要：

  Synthesis of phosphoramidate protides of carbocyclic D- and L-2',3'-dideoxy-2',3' -didehydro-7-deazaadenosine by treatment of the nucleoside with phosphorochloridates in the presence of pyridine and t-BuMgCl is described. Several of these protides showed significantly improved antiviral potency over the parent nucleosides against both HIV and HBV.

  DOI：

  10.1081/ncn-200040678
• 作为产物：
  描述：

  4,6-二氯嘧啶-5-乙醛 在 盐酸 、 ammonium chloride 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 生成 [(1S,4R)-4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-cyclopentene-1-yl]methanol
  参考文献：
  名称：

  Phosphoramidate Protides of Carbocyclic 2′,3′‐Dideoxy‐2′,3′‐Didehydro‐7‐Deazaadenosine with Potent Activity Against HIV and HBV

  摘要：

  Synthesis of phosphoramidate protides of carbocyclic D- and L-2',3'-dideoxy-2',3' -didehydro-7-deazaadenosine by treatment of the nucleoside with phosphorochloridates in the presence of pyridine and t-BuMgCl is described. Several of these protides showed significantly improved antiviral potency over the parent nucleosides against both HIV and HBV.

  DOI：

  10.1081/ncn-200040678

文献信息

• SYNTHESIS OF CARBOCYCLIC ANALOGS OF 2′,3′-DIDEOXYSANGIVAMYCIN, 2′,3′-DIDEOXYTOYOCAMYCIN, AND 2′,3′-DIDEOXYTRICIRIBINE
  作者：Kristjan S. Gudmundsson、Zhicheng Wang、Susan M. Daluge、Paul L. Feldman

  DOI：10.1081/ncn-100107193

  日期：2001.12.31

  activity of new carbocyclic analogs of 2', 3'-dideoxysangivamycin, 2',3'-dideoxytoyocamycin and 2',3'-dideoxytriciribine is described. The key intermediate, carbocyclic 4-chloro-5-iodopyrrolopyrimidine. was synthesized in good yield via a novel iodination method using I2 and CF3COOAg. This carbocyclic 4-chloro-5-iodopyrrolopyrimidine then allowed for a concise synthesis of the desired 4,5-disubstituted

  描述了新的2'，3'-双脱氧桑奇霉素，2'，3'-双脱氧代托卡霉素和2'，3'-双脱氧三丁胺的碳环类似物的合成和抗病毒活性。关键中间体，碳环4-氯-5-碘吡咯并嘧啶。通过使用I2和CF3COOAg的新型碘化方法，以高收率合成了SnO2。然后使该碳环的4-氯-5-碘吡咯并并嘧啶精制所需的4，5-二取代的碳环核苷。