cis-1-(3-hydroxymethyl-1,4-dioxepan-5-yl)-5-trifluoromethyluracil

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: cis-1-(3-hydroxymethyl-1,4-dioxepan-5-yl)-5-trifluoromethyluracil
• 英文别名: 1-[(3S,5S)-3-(hydroxymethyl)-1,4-dioxepan-5-yl]-5-(trifluoromethyl)pyrimidine-2,4-dione
• 化学式: C₁₁H₁₃F₃N₂O₅
• 分子量: 310.23
• InChiKey: ATVDSBODKOTFRV-XPUUQOCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-三氟甲基尿嘧啶 、 3-(acetoxymethyl)-5-methoxy-1,4-dioxepane 生成 trans-1-(3-hydroxymethyl-1,4-dioxepan-5-yl)-5-trifluoromethyluracil 、 cis-1-(3-hydroxymethyl-1,4-dioxepan-5-yl)-5-trifluoromethyluracil
  参考文献：
  名称：

  cis- and trans-1-[3-(Hydroxymethyl)-1,4-dioxepan-5-yl]pyrimidines: a new nucleoside prototype with a seven-membered moiety

  摘要：

  We synthesized nucleoside analogues with a seven-membered moiety as the carbohydrate fragment mimicking the upper part of biologically active natural and synthetic nucleosides, starting from 3-iodomethyl-5-methoxy-1,4-dioxepane. The reaction sequence involved the substitution of the iodine atom by the acetoxy group, condensation with the nucleobases and subsequent saponification. The cis/trans mixtures of the target compounds were separated by reversed-phase preparative HPLC. The relative configurations of each of the hydrogen atoms of the cia and trans newly synthesized compounds were determined by spin decoupling, 2D NOESY and COSY experiments. None of this series showed activity in antiviral tests in cell cultures. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00270-8

文献信息

• cis- and trans-1-[3-(Hydroxymethyl)-1,4-dioxepan-5-yl]pyrimidines: a new nucleoside prototype with a seven-membered moiety
  作者：Marı́a A Trujillo、José A Gómez、Joaquı́n Campos、Antonio Espinosa、Miguel A Gallo

  DOI：10.1016/s0040-4020(01)00270-8

  日期：2001.4

  We synthesized nucleoside analogues with a seven-membered moiety as the carbohydrate fragment mimicking the upper part of biologically active natural and synthetic nucleosides, starting from 3-iodomethyl-5-methoxy-1,4-dioxepane. The reaction sequence involved the substitution of the iodine atom by the acetoxy group, condensation with the nucleobases and subsequent saponification. The cis/trans mixtures of the target compounds were separated by reversed-phase preparative HPLC. The relative configurations of each of the hydrogen atoms of the cia and trans newly synthesized compounds were determined by spin decoupling, 2D NOESY and COSY experiments. None of this series showed activity in antiviral tests in cell cultures. (C) 2001 Elsevier Science Ltd. All rights reserved.