(+/-)-N⁶-(monomethoxytrityl)-9-[4-(ethoxycarbonyl)-3-cyclohexenyl]adenine | 188949-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (+/-)-N⁶-(monomethoxytrityl)-9-[4-(ethoxycarbonyl)-3-cyclohexenyl]adenine
• 英文别名: Ethyl 4-[6-[[(4-methoxyphenyl)-diphenylmethyl]amino]purin-9-yl]cyclohexene-1-carboxylate
• CAS: 188949-76-0
• 化学式: C₃₄H₃₃N₅O₃
• 分子量: 559.668
• InChiKey: OPUDHBYWOKXCCP-UHFFFAOYSA-N

物化性质

• 沸点：
  715.9±70.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  91.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+/-)-N⁶-(monomethoxytrityl)-9-[4-(ethoxycarbonyl)-3-cyclohexenyl]adenine 在 吡啶 、 sodium hydroxide 、 硼烷 、 双氧水 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 30.67h， 生成 (1R,2S,5R)-5-{6-[(4-Methoxy-phenyl)-diphenyl-methoxy]-purin-9-yl}-2-[(trityl-amino)-methyl]-cyclohexanol
  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 吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (+/-)-N⁶-(monomethoxytrityl)-9-[4-(ethoxycarbonyl)-3-cyclohexenyl]adenine
  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.