1-(9-benzylpurin-6-yl)-3-(1,3-dimethyluracil-5-yl)benzene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(9-benzylpurin-6-yl)-3-(1,3-dimethyluracil-5-yl)benzene
• 英文别名: 5-[3-(9-Benzylpurin-6-yl)phenyl]-1,3-dimethylpyrimidine-2,4-dione
• 化学式: C₂₄H₂₀N₆O₂
• 分子量: 424.462
• InChiKey: AOASPCVRKFLSIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3-双(三丁基甲锡烷基)苯 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-(9-benzylpurin-6-yl)-3-(1,3-dimethyluracil-5-yl)benzene
  参考文献：
  名称：

  Covalent analogues of DNA base-pairs and triplets. Part 3: Synthesis of 1,4- and 1,3-bis(purin-6-yl)benzenes and 1-(1,3-dimethyluracil-5-yl)-3 or 4-(purin-9-yl)benzenes

  摘要：

  The Stille cross-coupling reactions of 1,4- and 1,3-bis(trialkylstannyl)benzenes 2 or 3 with 9-benzyl-6-chloropurine (1) led either to mono-coupled 4- or 3-[(tributylstannyl)phenyl]benzenes 5a and 5b or to bis(9-benzylpurin-6-yl)benzenes (4a or 4b) depending on the ratio of the starting compounds, nature of the stannane and conditions. Analogous reaction of 1 with benzene-1,4-diboronic acid gave selectively 4a in good yield. The reaction of stannanes 5 with 1,3-dimethyl-5-iodouracil gave 1-(9-benzylpurin-6-yl)-4- or -3-(1,3-dimethyluracil-5-yl)benzenes (10a and 10b) in low yields. Compounds 4 and 10 are novel types of covalently linked analogues of nucleobase-pairs. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00833-5

文献信息

• Covalent analogues of DNA base-pairs and triplets. Part 3: Synthesis of 1,4- and 1,3-bis(purin-6-yl)benzenes and 1-(1,3-dimethyluracil-5-yl)-3 or 4-(purin-9-yl)benzenes
  作者：Martina Havelková、Dalimil Dvořák、Michal Hocek

  DOI：10.1016/s0040-4020(02)00833-5

  日期：2002.9

  The Stille cross-coupling reactions of 1,4- and 1,3-bis(trialkylstannyl)benzenes 2 or 3 with 9-benzyl-6-chloropurine (1) led either to mono-coupled 4- or 3-[(tributylstannyl)phenyl]benzenes 5a and 5b or to bis(9-benzylpurin-6-yl)benzenes (4a or 4b) depending on the ratio of the starting compounds, nature of the stannane and conditions. Analogous reaction of 1 with benzene-1,4-diboronic acid gave selectively 4a in good yield. The reaction of stannanes 5 with 1,3-dimethyl-5-iodouracil gave 1-(9-benzylpurin-6-yl)-4- or -3-(1,3-dimethyluracil-5-yl)benzenes (10a and 10b) in low yields. Compounds 4 and 10 are novel types of covalently linked analogues of nucleobase-pairs. (C) 2002 Elsevier Science Ltd. All rights reserved.