(+/-)-1-[4-(hydroxymethyl)-3-cyclohexenyl]thymine | 152388-44-8

• 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-[4-(hydroxymethyl)-3-cyclohexenyl]thymine
• 英文别名: 1-(4-(Hydroxymethyl)-3-cyclohexen-1-yl)-5-methyl-2,4(1H,3H)-pyrimidinedione；1-[4-(hydroxymethyl)cyclohex-3-en-1-yl]-5-methylpyrimidine-2,4-dione
• CAS: 152388-44-8
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: AORZNWDXZHYTKY-UHFFFAOYSA-N

物化性质

• 熔点：
  201-202 °C
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-1-[4-(hydroxymethyl)-3-cyclohexenyl]thymine 在 吡啶 、 sodium hydroxide 、 硼烷 、 双氧水 、 溶剂黄146 作用下， 反应 28.0h， 生成 (1RS,3RS,4SR)-1-[4-(hydroxymethyl)-3-hydroxycyclohexyl]thymine
  参考文献：
  名称：

  Synthesis and Conformational Study of 3-Hydroxy-4-(Hydroxymethyl)-1-Cyclohexanyl Purines and Pyrimidines

  摘要：

  The cyclohexane nucleosides with a 1,4-relationship between nucleoside base and hydroxymethyl moiety were synthesized using a conjugated addition reaction of the nucleobases to ethyl 1,3-cyclohexadiene-1-carboxylate and hydroboration of the cyclohexenyl precursor. The lack of antiviral activity of the compounds was correlated with the conformation of these nucleosides as deduced from NMR and X-ray analysis.

  DOI：

  10.1021/jo962204x
• 作为产物：
  描述：

  ethyl 1,3-cyclohexadiene-1-carboxylate 在 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.67h， 生成 (+/-)-1-[4-(hydroxymethyl)-3-cyclohexenyl]thymine
  参考文献：
  名称：

  Synthesis and Conformational Study of 3-Hydroxy-4-(Hydroxymethyl)-1-Cyclohexanyl Purines and Pyrimidines

  摘要：

  The cyclohexane nucleosides with a 1,4-relationship between nucleoside base and hydroxymethyl moiety were synthesized using a conjugated addition reaction of the nucleobases to ethyl 1,3-cyclohexadiene-1-carboxylate and hydroboration of the cyclohexenyl precursor. The lack of antiviral activity of the compounds was correlated with the conformation of these nucleosides as deduced from NMR and X-ray analysis.

  DOI：

  10.1021/jo962204x

文献信息

• Synthesis and Conformational Study of 3-Hydroxy-4-(Hydroxymethyl)-1-Cyclohexanyl Purines and Pyrimidines
  作者：Yuris Maurinsh、Jan Schraml、Hans De Winter、Norbert Blaton、Oswald Peeters、Eveline Lescrinier、Jef Rozenski、Arthur Van Aerschot、Erik De Clercq、Roger Busson、Piet Herdewijn

  DOI：10.1021/jo962204x

  日期：1997.5.1

  The cyclohexane nucleosides with a 1,4-relationship between nucleoside base and hydroxymethyl moiety were synthesized using a conjugated addition reaction of the nucleobases to ethyl 1,3-cyclohexadiene-1-carboxylate and hydroboration of the cyclohexenyl precursor. The lack of antiviral activity of the compounds was correlated with the conformation of these nucleosides as deduced from NMR and X-ray analysis.