9-[(1R,3S,4R)-4-Hydroxymethyl-3-hydroxycyclohexanyl]adenine | 233266-06-3

• 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-[(1R,3S,4R)-4-Hydroxymethyl-3-hydroxycyclohexanyl]adenine
• 英文别名: 9-[(1R,4S,5R)-3-hydroxy-4-hydroxymethylcyclohexanyl]adenine；9-[(1R,3S,4R)-3-Hydroxy-4-hydroxymethylcyclohexanyl]adenine；(1S,2R,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)cyclohexan-1-ol
• CAS: 233266-06-3
• 化学式: C₁₂H₁₇N₅O₂
• 分子量: 263.299
• InChiKey: QZEHMNCVKZWEHI-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-[(1R,3S,4R)-4-Hydroxymethyl-3-hydroxycyclohexanyl]adenine 在 吡啶 作用下， 反应 3.0h， 生成 N-[9-((1R,3S,4R)-3-Hydroxy-4-trimethylsilanyloxymethyl-cyclohexyl)-9H-purin-6-yl]-benzamide
  参考文献：
  名称：

  Maurinsh, Yuris; Rosemeyer, Helmut; Esnouf, Robert, Chemistry - A European Journal, 1999, vol. 5, # 7, p. 2139 - 2150

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,2R,5R)-5-(6-{[(4-Methoxy-phenyl)-diphenyl-methyl]-amino}-purin-9-yl)-2-trityloxymethyl-cyclohexanol 在 4-二甲氨基吡啶 、 氢氧化钾 、 水 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 9-[(1R,3S,4R)-4-Hydroxymethyl-3-hydroxycyclohexanyl]adenine
  参考文献：
  名称：

  Maurinsh, Yuris; Rosemeyer, Helmut; Esnouf, Robert, Chemistry - A European Journal, 1999, vol. 5, # 7, p. 2139 - 2150

  摘要：

  DOI：

文献信息

• CARBOCYCLIC NUCLEOSIDES AND PROCESS FOR OBTAINING SUCH
  申请人：Stichting REGA V.Z.W.

  公开号：EP1210347B1

  公开（公告）日：2004-06-23
• 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.
• Enantioselective Synthesis and Conformational Study of Cyclohexene Carbocyclic Nucleosides
  作者：Jing Wang、Piet Herdewijn

  DOI：10.1021/jo9908288

  日期：1999.10.1

  Enantioselective synthesis of a new family of unsaturated six-membered carbocyclic nucleosides using (R)-(-)-can one as starting material is described. Introduction of the base moiety via Mitsunobu reaction proceeded regio- and stereoselectively and with good chemical yield, while the Pd-coupling approach failed. H-1 NMR study and molecular modeling show the adenine compound exists in an equilibrium of H-3(2) and H-2(3) conformers (ratio 7:3) in favor of the 3'-endo half-chair conformation, with the base oriented in a pseudoaxial position. This conformational preference can be explained by the pi --> sigma*(C1')-(N1) interaction involving the antibonding orbital of the C1'-N bond.