1,4-bis(9-benzylpurin-6-yl)benzene | 494752-07-7

• 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: 1,4-bis(9-benzylpurin-6-yl)benzene
• 英文别名: 9H-Purine, 6,6'-(1,4-phenylene)bis[9-(phenylmethyl)-；9-benzyl-6-[4-(9-benzylpurin-6-yl)phenyl]purine
• CAS: 494752-07-7
• 化学式: C₃₀H₂₂N₈
• 分子量: 494.558
• InChiKey: SIMLYPBYYIHEOC-UHFFFAOYSA-N

物化性质

• 沸点：
  808.2±75.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-氯-9-(苯基甲基)-9H-嘌呤 、 1,4-苯二硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.0h， 以25%的产率得到1,4-bis(9-benzylpurin-6-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.