(Z)-3-(6-amino-9H-purin-9-yl)-3-(1-hydroxycyclohexyl)-2-propenenitrile | 1218924-53-8

• 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: (Z)-3-(6-amino-9H-purin-9-yl)-3-(1-hydroxycyclohexyl)-2-propenenitrile
• 英文别名: (Z)-3-(6-aminopurin-9-yl)-3-(1-hydroxycyclohexyl)prop-2-enenitrile
• CAS: 1218924-53-8
• 化学式: C₁₄H₁₆N₆O
• 分子量: 284.321
• InChiKey: DTFAUEKRTMNYMF-WMZJFQQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(1-羟基环己基)-2-丙炔腈 、 腺嘌呤 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以96%的产率得到(Z)-3-(6-amino-9H-purin-9-yl)-3-(1-hydroxycyclohexyl)-2-propenenitrile
  参考文献：
  名称：

  Chemo-, regio- and stereospecific addition of adenine and 8-azaadenine to α,β-acetylenic γ-hydroxy nitriles: a short-cut to novel acyclic adenosine analogues

  摘要：

  Adenine (9H-purin-6-amine) adds readily to available alpha,beta-acetylenic gamma-hydroxy nitriles under mild conditions (molar ratio 1 1, K2CO3, DMF, rt, 10 min) to afford chemo-, regio- and stereospecifically (Z)-3-(6-amino-9H-purin-9-yl)-4-hydroxy-4-alkyl-2-alkenenitriles novel functionalized acyclic nucleoside analogues (95-98% yield) Under similar conditions (K2CO3, DMF, rt, 1 h), 8-azaadenine (3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine) reacts with 4-hydroxy-4-methyl-2-pentynenitrile nonselectively at the 7-, 8- and 9-positions to give the corresponding adducts in a 1 10 5 9 ratio, the total yield being 81% Chemo-, regio- and stereospecific addiction of 8-azaadenine to the above alpha,beta,-acetylenic gamma-hydroxy nitriles leading to (Z)-3-(7-amino-2H-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-4-hydroxy-4-alkyl-2-alkenenitriles in 44-90% yield is attained when the reaction is carried Out without solvent in the presence Of Et3N (30 mol%), the molar ratio of 8-azaadenine alpha,beta-acetylenic nitriles being 1 2 0 (rt, 12-38 h) (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.01.015