(+/-)-9-[4-(ethoxycarbonyl)-3-cyclohexenyl]guanine | 188949-72-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (+/-)-9-[4-(ethoxycarbonyl)-3-cyclohexenyl]guanine
• 英文别名: ethyl 4-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)cyclohex-1-ene-1-carboxylate；ethyl 4-(2-amino-6-oxo-1H-purin-9-yl)cyclohexene-1-carboxylate
• CAS: 188949-72-6
• 化学式: C₁₄H₁₇N₅O₃
• 分子量: 303.321
• InChiKey: OHLOGTYKMAVARP-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-9-[4-(ethoxycarbonyl)-3-cyclohexenyl]guanine 在 吡啶 、 sodium hydroxide 、 硼烷 、 双氧水 、 二异丁基氢化铝 、 溶剂黄146 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 34.67h， 生成 (1RS,3SR,4RS)-9-[4-(hydroxymethyl)-3-hydroxycyclohexyl]guanine
  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：

  2-氨基-6-氯嘌呤 在 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 98.0h， 生成 (+/-)-9-[4-(ethoxycarbonyl)-3-cyclohexenyl]guanine
  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.