9-benzyl-2-chloro-6-phenyl-9H-purine | 164360-01-4

• 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: 9-benzyl-2-chloro-6-phenyl-9H-purine
• 英文别名: 9-Benzyl-2-chloro-8-phenylpurine；9-benzyl-2-chloro-6-phenylpurine
• CAS: 164360-01-4
• 化学式: C₁₈H₁₃ClN₄
• 分子量: 320.781
• InChiKey: CUWBCCIAROCSQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-benzyl-2-chloro-6-phenyl-9H-purine 在 palladium diacetate 、 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 64.0h， 生成 9-benzyl-2-(4-methoxyphenyl)-6-phenyl-8-(p-tolyl)-9H-purine
  参考文献：
  名称：

  Direct C−H Arylation of Purines:  Development of Methodology and Its Use in Regioselective Synthesis of 2,6,8-Trisubstituted Purines

  摘要：

  [GRAPHICS]Direct C-H arylation of purines to position 8 by diverse aryl iodides was achieved with Pd catalysis in the presence of CuI and Cs2CO3. The methodology is general and efficient and was applied in the consecutive regioselective synthesis of 2,6,8-trisubstituted purines bearing three different C-substituents in combination with two cross-coupling reactions.

  DOI：

  10.1021/ol062324j
• 作为产物：
  描述：

  2,6-二氯嘌呤 在 tetratrifurylphosphinepalladium 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 55.33h， 生成 9-benzyl-2-chloro-6-phenyl-9H-purine
  参考文献：
  名称：

  2,6-二卤尿嘌呤Stille偶联中的区域化学

  摘要：

  已经研究了2，6-二卤代尿烷在Stille偶联中的区域化学。2,6-二氯嘌呤在6-位选择性反应，6-氯-2-碘嘌呤和2-溴-6-氯嘌呤在2-位选择性反应。

  DOI：

  10.1016/0040-4020(96)00199-8

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。
• Regioselective Pd-mediated coupling between 2,6-dichloropurines and organometallic reagents
  作者：Lise-Lotte Gundersen、Geir Langli、Frode Rise

  DOI：10.1016/0040-4039(95)00163-7

  日期：1995.3

  Selective coupling in the purine 6-position has been achieved, by reacting N-benzylated 2,6-dichloropurines with organotin and organozinc reagents. The positional identity products were established from long range HETCOR or nOe NMR experiments.

  通过使N-苄基化的2,6-二氯嘌呤与有机锡和有机锌试剂反应，可以实现嘌呤6-位的选择性偶联。位置同一性产物是通过长距离HETCOR或nOe NMR实验确定的。
• Regiochemistry in Stille couplings of 2,6-dihalopurines
  作者：Geir Langli、Lise-Lotte Gundersen、Frode Rise

  DOI：10.1016/0040-4020(96)00199-8

  日期：1996.4

  The regiochemistry in Stille couplings of 2,6-dihalopurines have been studied. 2,6-Dichloropurines react selectively in the 6-position, and 6-chloro-2-iodopurines and 2-bromo-6-chloropurines in the 2-position.

  已经研究了2，6-二卤代尿烷在Stille偶联中的区域化学。2,6-二氯嘌呤在6-位选择性反应，6-氯-2-碘嘌呤和2-溴-6-氯嘌呤在2-位选择性反应。
• Direct C−H Arylation of Purines:  Development of Methodology and Its Use in Regioselective Synthesis of 2,6,8-Trisubstituted Purines
  作者：Igor Čerňa、Radek Pohl、Blanka Klepetářová、Michal Hocek

  DOI：10.1021/ol062324j

  日期：2006.11.9

  [GRAPHICS]Direct C-H arylation of purines to position 8 by diverse aryl iodides was achieved with Pd catalysis in the presence of CuI and Cs2CO3. The methodology is general and efficient and was applied in the consecutive regioselective synthesis of 2,6,8-trisubstituted purines bearing three different C-substituents in combination with two cross-coupling reactions.