1-[4-羟基-3-(羟甲基)丁-2-烯基]嘧啶-2,4-二酮 | 839674-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1-[4-羟基-3-(羟甲基)丁-2-烯基]嘧啶-2,4-二酮
• 英文名称: 1-[4-hydroxy-3-(hydroxymethyl)-2-butenyl]-2,4(1H,3H)-pyrimidinedione
• 英文别名: 1-[3,3'-bis(hydroxymethyl)-prop-2-enyl]uracil；1-[4-Hydroxy-3-(hydroxymethyl)but-2-enyl]pyrimidine-2,4-dione
• CAS: 839674-97-4
• 化学式: C₉H₁₂N₂O₄
• 分子量: 212.205
• InChiKey: NSLBMXWPFSHMDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[3,3'-bis(t-butyldimethylsilyloxymethyl)-prop-2-enyl]uracil 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以80%的产率得到1-[4-羟基-3-(羟甲基)丁-2-烯基]嘧啶-2,4-二酮
  参考文献：
  名称：

  Concise Synthesis and Antiviral Activity of Novel Unsaturated Acyclic Pyrimidine Nucleosides

  摘要：

  Novel acyclic nucleoside analogues were designed and synthesized as open-chain analogues of neplanocin A. The coupling of the allylic bromide with pyrimidine bases using cesium carbonate afforded a series of novel acyclic nucleosides. The synthesized compounds 15-22 were evaluated for their antiviral activity against various viruses such as HIV, HSV-1, HSV-2, and HCMV.

  DOI：

  10.1081/ncn-200051913

文献信息

• Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies
  作者：Franck Amblard、Steven P. Nolan、Raymond F. Schinazi、Luigi A. Agrofoglio

  DOI：10.1016/j.tet.2004.11.019

  日期：2005.1

  Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.
• Concise Synthesis and Antiviral Activity of Novel Unsaturated Acyclic Pyrimidine Nucleosides
  作者：Chang-Hyun Oh、Tae-Rim Baek、Joon Hee Hong

  DOI：10.1081/ncn-200051913

  日期：2005.2.1

  Novel acyclic nucleoside analogues were designed and synthesized as open-chain analogues of neplanocin A. The coupling of the allylic bromide with pyrimidine bases using cesium carbonate afforded a series of novel acyclic nucleosides. The synthesized compounds 15-22 were evaluated for their antiviral activity against various viruses such as HIV, HSV-1, HSV-2, and HCMV.