1-(1-acetyloxy-3-hydroxy-2-propyl)-5-fluorouracil | 210760-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(1-acetyloxy-3-hydroxy-2-propyl)-5-fluorouracil
• 英文别名: [2-(5-Fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxypropyl] acetate
• CAS: 210760-42-2
• 化学式: C₉H₁₁FN₂O₅
• 分子量: 246.195
• InChiKey: QRHGDSXAVPELKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(1-acetyloxy-3-hydroxy-2-propyl)-5-fluorouracil 在 氨 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 25.0~80.0 ℃ 、266.64 Pa 条件下， 反应 17.5h， 生成 [5-(5-Fluoro-2,4-dioxopyrimidin-1-yl)-1,3-dioxan-2-yl]methyl benzoate
  参考文献：
  名称：

  Ring-Expanded Nucleoside Analogues. 1,3-Dioxan-5-yl Pyrimidines

  摘要：

  1,3-Dioxan-5-yl pyrimidine nucleoside analogues, higher homologues of antiviral and anticancer 1,3-dioxolanes, were prepared from bis-1,3-tritylglycerol and 3-benzoylated bases (uracil, 5-fluorouracil, thymine). Mitsunobu condensation, deprotection, and cycloacetalization gave cis/trans mixtures of 2,5-disubstituted-1,3-dioxanes in which the desired cis stereoisomers predominated. Cytosine derivatives could not be obtained in this manner; N-4-benzoylcytosine afforded an O-2 alkylated Mitsunobu product that rearranged to an O-2-(2,3-dihydroxypropyl)cytosine on detritylation with aqueous acetic acid. Cytosine and 5-fluorocytosine nucleosides were therefore prepared from the corresponding uracils via their 1,2,4-triazole derivatives. H-1 NMR data established the conformational preference for equatorial 2'-hydroxymethyl and axial 5'-base in the cis isomers; the trans compounds were diequatorial. Despite their conformations, the cis nucleosides showed no antiviral activity.

  DOI：

  10.1021/jo9715231
• 作为产物：
  描述：

  3-Benzoyl-5-fluoro-1-(2-trityloxy-1-trityloxymethyl-ethyl)-1H-pyrimidine-2,4-dione 在 氨 、 溶剂黄146 作用下， 生成 1-(1,3-dihydroxy-2-propyl)-5-fluorouracil 、 1-(1-acetyloxy-3-hydroxy-2-propyl)-5-fluorouracil
  参考文献：
  名称：

  Ring-Expanded Nucleoside Analogues. 1,3-Dioxan-5-yl Pyrimidines

  摘要：

  1,3-Dioxan-5-yl pyrimidine nucleoside analogues, higher homologues of antiviral and anticancer 1,3-dioxolanes, were prepared from bis-1,3-tritylglycerol and 3-benzoylated bases (uracil, 5-fluorouracil, thymine). Mitsunobu condensation, deprotection, and cycloacetalization gave cis/trans mixtures of 2,5-disubstituted-1,3-dioxanes in which the desired cis stereoisomers predominated. Cytosine derivatives could not be obtained in this manner; N-4-benzoylcytosine afforded an O-2 alkylated Mitsunobu product that rearranged to an O-2-(2,3-dihydroxypropyl)cytosine on detritylation with aqueous acetic acid. Cytosine and 5-fluorocytosine nucleosides were therefore prepared from the corresponding uracils via their 1,2,4-triazole derivatives. H-1 NMR data established the conformational preference for equatorial 2'-hydroxymethyl and axial 5'-base in the cis isomers; the trans compounds were diequatorial. Despite their conformations, the cis nucleosides showed no antiviral activity.

  DOI：

  10.1021/jo9715231

文献信息

• Ring-Expanded Nucleoside Analogues. 1,3-Dioxan-5-yl Pyrimidines
  作者：Gina Cadet、Ching-See Chan、Rose Y. Daniel、Claudette P. Davis、Deodialsingh Guiadeen、George Rodriguez、Tamara Thomas、Sean Walcott、Peter Scheiner

  DOI：10.1021/jo9715231

  日期：1998.7.1

  1,3-Dioxan-5-yl pyrimidine nucleoside analogues, higher homologues of antiviral and anticancer 1,3-dioxolanes, were prepared from bis-1,3-tritylglycerol and 3-benzoylated bases (uracil, 5-fluorouracil, thymine). Mitsunobu condensation, deprotection, and cycloacetalization gave cis/trans mixtures of 2,5-disubstituted-1,3-dioxanes in which the desired cis stereoisomers predominated. Cytosine derivatives could not be obtained in this manner; N-4-benzoylcytosine afforded an O-2 alkylated Mitsunobu product that rearranged to an O-2-(2,3-dihydroxypropyl)cytosine on detritylation with aqueous acetic acid. Cytosine and 5-fluorocytosine nucleosides were therefore prepared from the corresponding uracils via their 1,2,4-triazole derivatives. H-1 NMR data established the conformational preference for equatorial 2'-hydroxymethyl and axial 5'-base in the cis isomers; the trans compounds were diequatorial. Despite their conformations, the cis nucleosides showed no antiviral activity.