9-苄基-6-(3-甲氧基苯基)嘌呤 | 83135-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 9-苄基-6-(3-甲氧基苯基)嘌呤
• 英文名称: 9-Benzyl-6-(3-methoxyphenyl)purine
• 英文别名: 9-Benzyl-6-(3-methoxyphenyl)-9H-purine
• CAS: 83135-04-0
• 化学式: C₁₉H₁₆N₄O
• 分子量: 316.362
• InChiKey: YTGSFSDFFSTUOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-苄基-6-(3-甲氧基苯基)嘌呤 在 亚硝酸特丁酯 、 氧气 、 palladium diacetate 作用下， 110.0 ℃ 、101.33 kPa 条件下， 以78%的产率得到9-benzyl-6-(5-methoxy-2-nitrophenyl)-9H-purine
  参考文献：
  名称：

  通过C（sp2）–H活化PdII催化的6芳基嘌呤的嘌呤定向邻位硝化：合成6（2-硝基芳基）嘌呤衍生物的实用方法

  摘要：

  在t BuONO / O 2存在下，Pd II催化6-芳基嘌呤的C（sp 2）-H活化可制得6-（2-硝基芳基）-嘌呤。嘌呤取代基充当硝化的邻位导向基团。

  DOI：

  10.1002/ejoc.201800567
• 作为产物：
  描述：

  6-氯-9-(苯基甲基)-9H-嘌呤 在 氢碘酸 、 碳酸氢钠 、 sodium thiosulfate 作用下， 以 丙酮 为溶剂， 反应 2.5h， 生成 9-苄基-6-(3-甲氧基苯基)嘌呤
  参考文献：
  名称：

  Coupling of diazopurines, a curious steric effect in a free radical reaction

  摘要：

  DOI：

  10.1021/jo00146a013

文献信息

• The Suzuki-Miyaura Cross-Coupling Reactionsof 2-, 6- or 8-Halopurines with Boronic Acids Leading to 2-, 6- or 8-Aryl- and -Alkenylpurine Derivatives
  作者：Martina Havelková、Dalimil Dvořak、Michal Hocek

  DOI：10.1055/s-2001-16765

  日期：——

  The Suzuki-Miyaura cross-coupling reactions of 9-benzyl-6-chloropurine, 9- or 3-benzyl-8-bromoadenine and 2,6-dihalopurines with boronic acids gave the corresponding 6-, 8- or 2-aryl- or -alkenylpurines in good yields. Anhydrous conditions in toluene were superior for coupling of electron-rich boronic acids, while aqueous DME was used for electron-poor arylboronic acids as well as for alkenylboronic acids. A good regioselectivity was observed for the coupling of 2,6-dihalopurines: 9-benzyl-2,6-dichloropurine reacted with one equivalent of phenyl boronic acid to give 9-benzyl-2-chloro-6-phenylpurine, while an analogous reaction of 9-benzyl-6-chloro-2-iodopurine gave selectively 9-benzyl-6-chloro-2-phenylpurine.

  9-苄基-6-氯嘌呤、9-或3-苄基-8-溴腺嘌呤及2,6-二卤嘌呤与硼酸进行的铃木-宫浦交叉偶联反应，以良好产率得到了相应的6-、8-或2-芳基或烯基嘌呤衍生物。无水条件下以甲苯为溶剂对于富电子硼酸的偶联反应较为有利，而贫电子芳基硼酸及烯基硼酸则以含水的二甲氧基乙烷(DME)为溶剂进行反应。在2,6-二卤嘌呤的偶联反应中可以观察到良好的区域选择性：9-苄基-2,6-二氯嘌呤与一当量苯硼酸反应得到了9-苄基-2-氯-6-苯基嘌呤，而9-苄基-6-氯-2-碘嘌呤的类似反应则高选择性地得到了9-苄基-6-氯-2-苯基嘌呤。
• The Suzuki-Miyaura Cross-Coupling Reactions of 6-Halopurines with Boronic Acids Leading to 6-Aryl- and 6-Alkenylpurines
  作者：Martina Havelková、Michal Hocek、Michal Česnek、Dalimil Dvořák

  DOI：10.1055/s-1999-2753

  日期：1999.7
• Selective anti-tubercular purines: Synthesis and chemotherapeutic properties of 6-aryl- and 6-heteroaryl-9-benzylpurines
  作者：Morten Brændvang、Lise-Lotte Gundersen

  DOI：10.1016/j.bmc.2005.06.054

  日期：2005.12

  6-Aryl- and 6-heteroaryl-9-benzylpurines have been synthesized employing palladium-catalyzed coupling reactions in the step forming the C-C or C-N bond between the aryl- or heteroaryl and the purine. The compounds were screened for activity against Mycobacterium tuberculosis as well as representative Gram+ and Gram- bacteria, and for cytotoxic effects on mammalian cells. Several potent antimycobacterials were identified. These compounds probably act by a novel and selective mechanism; they exhibit low toxicity toward other bacteria as well as mammalian cells. (c) 2005 Elsevier Ltd. All rights reserved.