1-(1,3-dihydroxy-2-propyl)thymine | 191802-81-0

• 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-(1,3-dihydroxy-2-propyl)thymine
• 英文别名: 1-(1,3-dihydroxypropan-2-yl)-5-methylpyrimidine-2,4-dione
• CAS: 191802-81-0
• 化学式: C₈H₁₂N₂O₄
• 分子量: 200.194
• InChiKey: WIBMRDHGRBLFIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.63
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.32
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-(1,3-dihydroxy-2-propyl)thymine 在 氨 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 80.0 ℃ 、266.64 Pa 条件下， 反应 2.5h， 生成 cis-1-[2-(hydroxymethyl)-1,3-dioxan-5-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
  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：

  5-Methyl-1-(2-trityloxy-1-trityloxymethyl-ethyl)-1H-pyrimidine-2,4-dione 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.5h， 以82%的产率得到1-(1,3-dihydroxy-2-propyl)thymine
  参考文献：
  名称：

  Synthesis of Six-Membered Nucleoside Analogs. Part 1: Pyrimidine Nucleosides Based on the 1,3-Dioxane Ring System

  摘要：

  The synthesis of pyrimidine nucleosides, cis-N-1-[(2-hydroxymethyl)-1,3-dioxan-5-yl]uracil (4) cis-N-1-[(2-hydroxymethyl)-1,3-dioxan-5-yl]thymine (5) and cis-N-1-[(2-hydroxymethyl)-1,3-dioxan-5-yl]cytosine (6) and their corresponding trans isomers is described. Compound 4 showed modest, selective activity against human immunodeficiency virus in acutely infected primary human lymphocytes.

  DOI：

  10.1080/07328319708001358