1-(2-hydroxy-1-hydroxymethyl-ethyl)-1H-pyrimidine-2,4-dione | 59237-80-8

• 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-(2-hydroxy-1-hydroxymethyl-ethyl)-1H-pyrimidine-2,4-dione
• 英文别名: Pyrimidine-2,4(1H,3H)-dione, 1-[1-(hydroxymethyl)-2-hydroxyethyl]-；1-(1,3-dihydroxypropan-2-yl)pyrimidine-2,4-dione
• CAS: 59237-80-8
• 化学式: C₇H₁₀N₂O₄
• 分子量: 186.167
• InChiKey: ACSDBZFQEPIONY-UHFFFAOYSA-N

物化性质

• 熔点：
  153-155 °C
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-1-hydroxymethyl-ethyl)-1H-pyrimidine-2,4-dione 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 trans-1-[2-(hydroxymethyl)-1,3-dioxan-5-yl]pyrimidine-2,4-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：

  N-1-(bistrityloxymethyl)methyluracil 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.5h， 以67%的产率得到1-(2-hydroxy-1-hydroxymethyl-ethyl)-1H-pyrimidine-2,4-dione
  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

文献信息

• Synthesis and structure of 2?-substituted 1-(1,3-dioxan-5-yl)uracils. Positive role of the Eu(fod)3 nmr shift reagent
  作者：Yu. Yu. Samitov、I. N. Goncharova、N. P. Ramzaeva、A. F. Mishnev、Ya. Ya. Bleidelis

  DOI：10.1007/bf00506463

  日期：1981.11
• SAMITOV, YU. YU.;GONCHAROVA, I. N.;RAMZAEVA, N. P.;MISHNEV, A. F.;BLEJDEL+, XIMIYA GETEROTSIKL. SOEDIN., 1981, N 11, 1523-1531
  作者：SAMITOV, YU. YU.、GONCHAROVA, I. N.、RAMZAEVA, N. P.、MISHNEV, A. F.、BLEJDEL+

  DOI：——

  日期：——
• NOVEL PRODRUGS FOR PHOSPHORUS-CONTAINING COMPOUNDS
  申请人：Metabasis Therapeutics, Inc.

  公开号：EP1060182B1

  公开（公告）日：2012-12-19
• Synthesis of Six-Membered Nucleoside Analogs. Part 1: Pyrimidine Nucleosides Based on the 1,3-Dioxane Ring System
  作者：Daniel C. Capaldi、Alessandra Eleuteri、Qin Chen、Raymond F. Schinazi

  DOI：10.1080/07328319708001358

  日期：1997.4

  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.
• 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.