1-[1-(diisopropoxyphosphorylmethoxymethyl)cyclopent-3-enylmethyl]thymine | 918887-29-3

• 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-(diisopropoxyphosphorylmethoxymethyl)cyclopent-3-enylmethyl]thymine
• 英文别名: 1-[[1-(Diisopropoxyphosphorylmethoxymethyl)cyclopent-3-en-1-yl]methyl]-5-methyl-pyrimidine-2,4-dione；1-[[1-[di(propan-2-yloxy)phosphorylmethoxymethyl]cyclopent-3-en-1-yl]methyl]-5-methylpyrimidine-2,4-dione
• CAS: 918887-29-3
• 化学式: C₁₉H₃₁N₂O₆P
• 分子量: 414.439
• InChiKey: SEIMHICFJZPEOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-[1-(diisopropoxyphosphorylmethoxymethyl)cyclopent-3-enylmethyl]thymine 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到1-[1-(dihydroxyphosphorylmethoxymethyl)cyclopent-3-enylmethyl]thymine
  参考文献：
  名称：

  新型5'-去碳环膦酸核苷的合成及抗病毒评价

  摘要：

  本文介绍了一种非常简单的合成新5'-降碳环核苷酸的途径。在标准亲核取代（K2CO3、18-Crown-6，DMF）下，甲磺酸酯17和18与天然核苷碱基（A，U，T，C）的缩合和脱保护得到目标核苷酸类似物27-34。此外，评估了这些化合物对各种病毒的抗病毒特性。

  DOI：

  10.1080/15257770600793927
• 作为产物：
  描述：

  二烯丙基丙二酸二乙酯 在 咪唑 、 lithium aluminium tetrahydride 、 Grubbs catalyst first generation 、 18-冠醚-6 、 四丁基氟化铵 、 potassium carbonate 、 三乙胺 、 lithium iodide 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 1-[1-(diisopropoxyphosphorylmethoxymethyl)cyclopent-3-enylmethyl]thymine
  参考文献：
  名称：

  Simple Synthesis and Anti-HIV Activity of Novel Cyclopentene Phosphonate Nucleosides

  摘要：

  A very simple synthetic route for novel cyclopentene phosphonate nucleosides is described. The characteristic cyclopentene moiety 6 was constructed via a ring-closing metathesis of divinyl 5, which could be readily prepared from diethylmalonate. The condensation of the mesylate 11 with nucleobases ( A, C, T, U) under nucleophilic substitution conditions ( K2CO3, 18-Crown-6, DMF) afforded the target nucleosides 12, 13, 14, and 15. In addition, the antiviral evaluations against various viruses were performed.

  DOI：

  10.1080/15257770500377698

文献信息

• Simple Synthesis and Anti-HIV Activity of Novel Cyclopentene Phosphonate Nucleosides
  作者：Aihong Kim、Joon Hee Hong

  DOI：10.1080/15257770500377698

  日期：2006.1

  A very simple synthetic route for novel cyclopentene phosphonate nucleosides is described. The characteristic cyclopentene moiety 6 was constructed via a ring-closing metathesis of divinyl 5, which could be readily prepared from diethylmalonate. The condensation of the mesylate 11 with nucleobases ( A, C, T, U) under nucleophilic substitution conditions ( K2CO3, 18-Crown-6, DMF) afforded the target nucleosides 12, 13, 14, and 15. In addition, the antiviral evaluations against various viruses were performed.
• Synthesis and Antiviral Evaluation of Novel 5′-Norcarboacyclic Phosphonic Acid Nucleosides
  作者：Aihong Kim、Joon Hee Hong

  DOI：10.1080/15257770600793927

  日期：2006.9

  This article describes a very simple route for synthesizing a novel 5′-norcarboacyclic nucleotides. The condensation of the mesylates 17 and 18 with the natural nucleosidic bases (A,U,T,C) under standard nucleophilic substitution (K2CO3, 18-Crown-6, DMF) and deprotection afforded the target nucleotide analogues 27–34. In addition, these compounds were evaluated for their antiviral properties against

  本文介绍了一种非常简单的合成新5'-降碳环核苷酸的途径。在标准亲核取代（K2CO3、18-Crown-6，DMF）下，甲磺酸酯17和18与天然核苷碱基（A，U，T，C）的缩合和脱保护得到目标核苷酸类似物27-34。此外，评估了这些化合物对各种病毒的抗病毒特性。