9-苄基-2-氯-6-甲基嘌呤 | 164360-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 9-苄基-2-氯-6-甲基嘌呤
• 英文名称: 9-benzyl-2-chloro-6-methyl-9H-purine
• 英文别名: 9-benzyl-2-chloro-6-methylpurine
• CAS: 164360-03-6
• 化学式: C₁₃H₁₁ClN₄
• 分子量: 258.71
• InChiKey: REPKRWPDMZCIJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  9-苄基-2,6-二氯-9h-嘌呤	9-benzyl-2,6-dichloro-9H-purine	79064-26-9	C12H8Cl2N4	279.128

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	9-benzyl-6-methyl-2-phenylpurine	571165-05-4	C19H16N4	300.363
  ——	9-benzyl-6-methyl-2-phenyl-8-(p-tolyl)-9H-purine	——	C26H22N4	390.487

反应信息

• 作为反应物：
  描述：

  9-苄基-2-氯-6-甲基嘌呤 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 63.0h， 生成 9-benzyl-6-methyl-2-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：

  9-苄基-2,6-二氯-9h-嘌呤 、 zinc methyl bromide 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 以69%的产率得到9-苄基-2-氯-6-甲基嘌呤
  参考文献：
  名称：

  Pd介导的2,6-二氯嘌呤和有机金属试剂之间的区域选择性偶联

  摘要：

  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。

  DOI：

  10.1016/0040-4039(95)00163-7

文献信息

• 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。
• An Efficient Synthesis of 2-Substituted 6-Methylpurine Bases and Nucleosides by Fe- or Pd-Catalyzed Cross-Coupling Reactions of 2,6-Dichloropurines
  作者：Michal Hocek、Hana Dvořáková

  DOI：10.1021/jo034351i

  日期：2003.7.1

  Fe-catalyzed cross-coupling reactions of 9-substituted or protected 2,6-dichloropurines with 1 equiv of methylmagnesium chloride gave regioselectively 2-chloro-6-methylpurines in good yields. The same reactions with 3 equiv of methylmagnesium chloride or Pd-catalyzed reactions with trimethylaluminum afforded 2,6-dimethylpurines. The 2-chloro-6-methylpurines underwent another coupling with phenylboronic

  铁的9-取代或受保护的2,6-二氯嘌呤与1当量的甲基氯化镁的铁催化交叉偶联反应以良好的产率得到了区域选择性的2-氯-6-甲基嘌呤。与3当量的甲基氯化镁的相同反应或与三甲基铝的Pd催化的反应提供2，6-二甲基嘌呤。将2-氯-6-甲基嘌呤与苯基硼酸再进行偶联，得到6-甲基-2-苯基嘌呤。所有反应均针对Bn和THP保护的嘌呤碱基以及酰基保护的核糖苷和2-脱氧核糖苷进行。脱保护后，获得游离嘌呤碱基和核苷。
• Synthesis of Purinecarbonitriles by Pd(0)-Catalysed Coupling of Halopurines with Zinc Cyanide.
  作者：Lise-Lotte Gundersen、Klaus Bechgaard、Klaus Bechgaard、Jon Songstad、Markku Leskelä、Mika Polamo、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0058

  日期：——

  Pd(0)-catalysed coupling of halopurines with zinc cyanide allows the smooth introduction of the cyano group into the purine 2-, 6- and 8-positions. Pronounced ligand effects were observed, and tetrakis(tri-2-furylphosphine)palladium(0) was found to be the catalyst of choice in reactions where tetrakis(triphenylphosphine)palladium(0) failed.
• Guo, Hai-Ming; Mao, Zhi-Jie; Niu, Hong-Ying, ARKIVOC, 2010, vol. 2010, # 9, p. 300 - 307
  作者：Guo, Hai-Ming、Mao, Zhi-Jie、Niu, Hong-Ying、Wang, Dong-Chao、Zhang, Gui-Sheng、Qu, Gui-Rong

  DOI：——

  日期：——
• [EN] HERBICIDAL COMPOUNDS<br/>[FR] COMPOSÉS HERBICIDES
  申请人：SYNGENTA LTD

  公开号：WO2011045561A2

  公开（公告）日：2011-04-21

  The present invention relates to substituted heterobicyclic carboxylic acid derivatives, as well as N-oxides and agriculturally acceptable salts thereof, and their use in controlling plant growth, particularly undesirable plant growth, in crops of useful plants. The invention extends to herbicidal compositions comprising such compounds, N-oxides and/or salts as well as mixtures of the same with one or more further active ingredients and/or a safener.