9-benzyl-6-ethyl-9H-purine

• 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: 9-benzyl-6-ethyl-9H-purine
• 英文别名: 6-ethyl-9-benzylpurine；9-benzyl-6-ethylpurine
• 化学式: C₁₄H₁₄N₄
• 分子量: 238.292
• InChiKey: VAYOKJIDTYDQJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  9-benzyl-6-ethynyl-9H-purine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 9-benzyl-6-ethyl-9H-purine
  参考文献：
  名称：

  通过亲核试剂与 6-乙烯基嘌呤和 6-乙炔基嘌呤的共轭加成合成带有官能化 C-取代基的嘌呤

  摘要：

  通过将 N-、O-和 S-亲核试剂共轭加成到 6-乙烯基嘌呤或 6-乙炔基嘌呤，制备在 6 位带有多种 β-取代乙基或乙烯基的嘌呤。系统地研究了这种方法的范围。将胺、醇化物和硫醇化物添加到 6-乙烯基嘌呤中得到相应的 6-(2-氨基乙基)-、6-(2-烷氧基乙基)-和 6-[2-(烷基硫基)乙基]嘌呤。胺与 6-乙炔基嘌呤的加成得到 6-(2-氨基乙烯基)嘌呤，而醇化物和硫醇化物的加入得到 6-(2-二烷氧基乙基)-和 6-[2-双(烷基硫基)乙基]嘌呤。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200600545

文献信息

• Selective Magnesiation of Chloro-iodopurines:  An Efficient Approach to New Purine Derivatives
  作者：Tomáš Tobrman、Dalimil Dvořák

  DOI：10.1021/ol053013w

  日期：2006.3.1

  selective I/Mg exchange reaction with iPrMgCl at -80 degrees C. The reaction course at 0 degrees C is different. Magnesiation of 1 proceeds with the migration of magnesium to the 8 position of the purine nuclei. In the case of 4, substitution of iodine with an alkyl group from the Grignard reagent accompanied with a Cl/Mg exchange reaction takes place, and 6-alkyl-2-magnesiated purines (9) are formed

  [反应：请参见文本] 6-氯-2-碘-9-异丙基嘌呤（1）和2-氯-6-碘-9-苄基嘌呤（4）与iPrMgCl在-80度进行选择性I / Mg交换反应C.在0摄氏度下的反应过程是不同的。1的镁化随着镁向嘌呤核的8位迁移而进行。在4的情况下，伴随着Cl / Mg交换反应，由格氏试剂中的烷基进行碘的取代，生成6-烷基-2-镁化的嘌呤（9）。如此制备的格氏试剂通过与醛反应得到相应的醇。
• Microwave promoted C6-alkylation of purines through SNAr-based reaction of 6-chloropurines with 3-alkyl-acetylacetone
  作者：Hai-Ming Guo、Yu Zhang、Hong-Ying Niu、Dong-Chao Wang、Zhi-Liang Chu、Gui-Rong Qu

  DOI：10.1039/c0ob01213k

  日期：——

  C6-Alkylated purine analogues were obtained in good to excellent isolated yields by SNAr reaction of 6-chloropurine derivatives with 3-alkyl-acetylacetone. 3-Alkyl-acetylacetones were employed as alkylating agents and C6-alkylated purines were obtained highly selectively within short reaction time under microwave irradiation conditions. This work is complementary to the classical coupling reactions for the synthesis of C6-alkylated purine analogues.

  通过 6-氯嘌呤衍生物与 3-烷基-乙酰丙酮的 SNAr 反应，以良好至极佳的分离产率获得了 C6-烷基化嘌呤类似物。采用 3-烷基乙酰丙酮作为烷化剂，在微波辐照条件下，在很短的反应时间内高选择性地获得了 C6-烷基化嘌呤。这项工作是对合成 C6-烷基化嘌呤类似物的经典偶联反应的补充。
• ‘Reductive Heck reaction’ of 6-halopurines
  作者：Tomáš Tobrman、Dalimil Dvořák

  DOI：10.1016/j.tetlet.2003.10.181

  日期：2004.1

  Alkenylation of 9-benzyl-6-hatopurines with alkenes does not proceed under conventional Heck conditions. However, in the presence of triethylammonium formate a mixture of the corresponding saturated products was obtained. In contrast to the classical Heck reaction, the regioselectivity of this process is low giving a mixture of both alpha- and beta-products regardless of the electronic nature of the substituent on the double bond of the alkene. (C) 2003 Elsevier Ltd. All rights reserved.
• Regio-controlled radical substitution of 9-substituted purines
  作者：Laurent Désaubry、Jean-Jacques Bourguignon

  DOI：10.1016/0040-4039(95)01647-z

  日期：1995.10

  9-benzylpurine undergoes facile radical alkylation and acylation under standard Minisci's conditions affording regioselectively 6-substituted derivatives.
• Synthesis of Purines Bearing Functionalized C-Substituents by the Conjugate Addition of Nucleophiles to 6-Vinylpurines and 6-Ethynylpurines
  作者：Martin Kuchař、Radek Pohl、Ivan Votruba、Michal Hocek

  DOI：10.1002/ejoc.200600545

  日期：2006.11

  Purines bearing diverse β-substituted ethyl or vinyl groups in position 6 were prepared by the conjugate addition of N-, O- and S-nucleophiles to 6-vinylpurines or 6-ethynylpurines. The scope of this methodology was systematically studied. The addition of amines, alcoholates and thiolates to 6-vinylpurines gave the corresponsing 6-(2-aminoethyl)-, 6-(2-alkoxyethyl)- and 6-[2-(alkylsulfanyl)ethyl]purines

  通过将 N-、O-和 S-亲核试剂共轭加成到 6-乙烯基嘌呤或 6-乙炔基嘌呤，制备在 6 位带有多种 β-取代乙基或乙烯基的嘌呤。系统地研究了这种方法的范围。将胺、醇化物和硫醇化物添加到 6-乙烯基嘌呤中得到相应的 6-(2-氨基乙基)-、6-(2-烷氧基乙基)-和 6-[2-(烷基硫基)乙基]嘌呤。胺与 6-乙炔基嘌呤的加成得到 6-(2-氨基乙烯基)嘌呤，而醇化物和硫醇化物的加入得到 6-(2-二烷氧基乙基)-和 6-[2-双(烷基硫基)乙基]嘌呤。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)