(+/-)-cis-9H-9-[2-(hydroxymethyl)cyclohexyl]adenine

• 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: (+/-)-cis-9H-9-[2-(hydroxymethyl)cyclohexyl]adenine
• 化学式: C₁₂H₁₇N₅O
• 分子量: 247.3
• InChiKey: YEJNIDAYLNVPGM-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  89.85
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-(R)-cis-2-aminocyclohexanemethanol 在 盐酸 、 ammonium hydroxide 、 三乙胺 作用下， 以 1,4-二氧六环 、 正丁醇 为溶剂， 反应 42.0h， 生成 (+/-)-cis-9H-9-[2-(hydroxymethyl)cyclohexyl]adenine
  参考文献：
  名称：

  1,2-Disubstituted cyclohexane nucleosides: comparative study for the synthesis of cis and trans adenosine analogues

  摘要：

  A new class of adenosine analogues with 1,2-disubstituted carbocycles (with cis and trans stereochemistry) have been synthesized. Construction of the base on the amino group of (+/-)-cis-(2-aminocyclohexyl)methanol was more efficient than the Mitsunobu condensation between the purine base and protected (+/-)-trans-(2-hydroxymethyl)cyclohexanol. The latter strategy gave the final compound with cis stereochemistry in a short number of steps with the overall yield depending on the nature of the protecting group on the hydroxymethyl group of the diol. However, Mitsunobu condensation between a purine base and the protected (+/-)-cis-(2-hydroxymethyl)cyclohexanol is not an ideal method to obtain trans purine derivatives because the elimination reaction is faster than the substitution reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.076

文献信息

• Purine Derivatives of 1,2-Disubstituted Cyclohexane Analogues of Nucleosides
  作者：C. Terán、L. Santana、E. Uriarte、D. Viña、E. De Clercq

  DOI：10.1081/ncn-120022635

  日期：2003.10

  Starting from (+/-)-cis-2-hydroxymethylcyclohexylamine, a series of cyclohexane-derived cis-1,2-disubstituted carbonucleoside analogues with a 6- or 2,6-purine or 8-azapurine base were synthesized. The antiviral and antitumoral in vitro effects of the new compounds were evaluated.
• 1,2-DISUBSTITUTED CYCLOHEXANE CARBOCYCLIC ANALOGUES OF NUCLEOSIDES
  作者：D. Viña、L. Santana、E. Uriarte

  DOI：10.1081/ncn-100002556

  日期：2001.3.31

  Several compounds of a new series of cyclohexane-based 1,2-disubstituted carbonucleoside analogues, were synthesized. The adenine and uridine derivatives, were prepared by construction of the heterocyclic base on the primary amino group of 2-aminocyclohexylmethanol, and the thymine derivative by condensation of 2-hydroxycyclohexylmethanol with thymine using the Mitsunobu reaction.
• 1,2-Disubstituted cyclohexane nucleosides: comparative study for the synthesis of cis and trans adenosine analogues
  作者：Dolores Viña、Lourdes Santana、Eugenio Uriarte、Carmen Terán

  DOI：10.1016/j.tet.2004.10.076

  日期：2005.1

  A new class of adenosine analogues with 1,2-disubstituted carbocycles (with cis and trans stereochemistry) have been synthesized. Construction of the base on the amino group of (+/-)-cis-(2-aminocyclohexyl)methanol was more efficient than the Mitsunobu condensation between the purine base and protected (+/-)-trans-(2-hydroxymethyl)cyclohexanol. The latter strategy gave the final compound with cis stereochemistry in a short number of steps with the overall yield depending on the nature of the protecting group on the hydroxymethyl group of the diol. However, Mitsunobu condensation between a purine base and the protected (+/-)-cis-(2-hydroxymethyl)cyclohexanol is not an ideal method to obtain trans purine derivatives because the elimination reaction is faster than the substitution reaction. (C) 2004 Elsevier Ltd. All rights reserved.