diethyl 5-(6-chloro-9H-purin-9-yl)-1,1-difluorohexylphosphonate | 876939-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: diethyl 5-(6-chloro-9H-purin-9-yl)-1,1-difluorohexylphosphonate
• CAS: 876939-29-6
• 化学式: C₁₅H₂₂ClF₂N₄O₃P
• 分子量: 410.788
• InChiKey: OPMYPBSBORRZSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  79.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  diethyl 5-(6-chloro-9H-purin-9-yl)-1,1-difluorohexylphosphonate 在 盐酸 、 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 [1,1-Difluoro-5-(6-oxo-1,6-dihydro-purin-9-yl)-hexyl]-phosphonic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of 9-(5′,5′-difluoro-5′-phosphonopentyl)guanine derivatives for PNP-inhibitors

  摘要：

  9-(5',5'-Difluoro-5'-phosphonopentyl)guanine (DFPP-G) and its hypoxanthine analogue (DFPP-H) were modified by introducing a methyl group to all possible positions of the linker connecting a purine and difluoromethylenephosphonic acid moiety to evaluate the effects of the methyl group on inhibition against purine nucleoside phosphorylase. The methyl group on the linker affected the inhibition in a positional-dependent manner. Inhibitory potency of alpha-methyl and beta-methyl -substituted analogues of DFPP-H increased by about 600- to 1000-fold upon converting to cyclopropane nucleotide analogue (+/-)-4. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.017
• 作为产物：
  描述：

  diethyl 1,1-difluoro-5-hydroxypentylphosphonate 在 偶氮二甲酸二异丙酯 、 戴斯-马丁氧化剂 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 diethyl 5-(6-chloro-9H-purin-9-yl)-1,1-difluorohexylphosphonate
  参考文献：
  名称：

  Synthesis and biological evaluation of 9-(5′,5′-difluoro-5′-phosphonopentyl)guanine derivatives for PNP-inhibitors

  摘要：

  9-(5',5'-Difluoro-5'-phosphonopentyl)guanine (DFPP-G) and its hypoxanthine analogue (DFPP-H) were modified by introducing a methyl group to all possible positions of the linker connecting a purine and difluoromethylenephosphonic acid moiety to evaluate the effects of the methyl group on inhibition against purine nucleoside phosphorylase. The methyl group on the linker affected the inhibition in a positional-dependent manner. Inhibitory potency of alpha-methyl and beta-methyl -substituted analogues of DFPP-H increased by about 600- to 1000-fold upon converting to cyclopropane nucleotide analogue (+/-)-4. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.017