1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(4-nitro-phenoxy)-1H-pyrimidin-2-one | 189005-88-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(4-nitro-phenoxy)-1H-pyrimidin-2-one
• 英文别名: 4-O-(4-nitrophenyl)uridine
• CAS: 189005-88-7
• 化学式: C₁₅H₁₅N₃O₈
• 分子量: 365.299
• InChiKey: MPMZHDZCOGRKPO-FMKGYKFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.44
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  157.18
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  sodium methylate 、 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(4-nitro-phenoxy)-1H-pyrimidin-2-one 以 甲醇 为溶剂， 反应 1.0h， 以87%的产率得到1-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-4-甲氧基嘧啶-2-酮
  参考文献：
  名称：

  Convenient Intermediates for the Preparation ofC-4 Modified Derivatives of Pyrimidine Nucleosides

  摘要：

  4-(4-Nitrophenoxy)-1-(beta-D-ribofuranosyl)pyrimidin-2(1H)-one 15, 5-methyl-4-(1,2,4-triazol-1-yl)-1-(beta-D-2-deoxyribofuranosyl 7a and 4-(4-nitrophenoxy)-1-(beta-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 17a, respectively, have been prepared and are recommended as reactive intermediates for the preparation of derivatives of uridine, thymidine and 2'-deoxyuridine which are modified at C-4.

  DOI：

  10.1080/07328319708002521
• 作为产物：
  描述：

  尿嘧啶核苷 在 三氯氧磷 作用下， 以 甲醇 、 溶剂黄146 、 三乙胺 、 乙腈 为溶剂， 反应 9.25h， 生成 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-(4-nitro-phenoxy)-1H-pyrimidin-2-one
  参考文献：
  名称：

  Convenient Intermediates for the Preparation ofC-4 Modified Derivatives of Pyrimidine Nucleosides

  摘要：

  4-(4-Nitrophenoxy)-1-(beta-D-ribofuranosyl)pyrimidin-2(1H)-one 15, 5-methyl-4-(1,2,4-triazol-1-yl)-1-(beta-D-2-deoxyribofuranosyl 7a and 4-(4-nitrophenoxy)-1-(beta-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 17a, respectively, have been prepared and are recommended as reactive intermediates for the preparation of derivatives of uridine, thymidine and 2'-deoxyuridine which are modified at C-4.

  DOI：

  10.1080/07328319708002521