(Z)-3-(6-amino-9H-purin-9-yl)-4-hydroxy-4-methyl-2-pentenenitrile | 1218924-50-5

• 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)-4-hydroxy-4-methyl-2-pentenenitrile
• 英文别名: (Z)-3-(6-aminopurin-9-yl)-4-hydroxy-4-methylpent-2-enenitrile
• CAS: 1218924-50-5
• 化学式: C₁₁H₁₂N₆O
• 分子量: 244.256
• InChiKey: BZYHJQANAGYVSD-CLTKARDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  腺嘌呤 、 3-hydroxy-3-methyl-1-cyano-1-butyne 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以98%的产率得到(Z)-3-(6-amino-9H-purin-9-yl)-4-hydroxy-4-methyl-2-pentenenitrile
  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

文献信息

• 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
  作者：Boris A. Trofimov、Anastasiya G. Mal'kina、Valentina V. Nosyreva、Olesya A. Shemyakina、Angela P. Borisova、Lyudmila I. Larina、Olga N. Kazheva、Grigorii G. Alexandrov、Oleg A. Dyachenko

  DOI：10.1016/j.tet.2010.01.015

  日期：2010.2

  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