9-benzyl-6-(hex-1-yn-1-yl)purine | 477301-06-7

• 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-(hex-1-yn-1-yl)purine
• 英文别名: 9-Benzyl-6-hex-1-ynylpurine；9-benzyl-6-hex-1-ynylpurine
• CAS: 477301-06-7
• 化学式: C₁₈H₁₈N₄
• 分子量: 290.368
• InChiKey: RBZSSASICYRZFP-UHFFFAOYSA-N

物化性质

• 沸点：
  494.0±55.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  2,2-二丙炔基丙二酸二乙酯 、 9-benzyl-6-(hex-1-yn-1-yl)purine 在 bis(triphenylphosphine)nickel(II) diiodide 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以52%的产率得到Diethyl 5-(9-benzylpurin-6-yl)-6-butyl-1,3-dihydroindene-2,2-dicarboxylate
  参考文献：
  名称：

  [2+2+2]-Co-cyclotrimerization 6-alkynylpurines with diynes: a method for preparation of 6-arylpurines

  摘要：

  A novel approach to 6-arylpurines based on [2+2+2]-co-cyclotrimerization of 6-alkynylpurines with various alpha,omega-diynes is described. Co-cyclotrimerization is catalyzed by Ni- and Co-phosphine catalysts and their choice depends on the substitution pattern of the both reactants. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02643-6
• 作为产物：
  描述：

  6-氯-9-(苯基甲基)-9H-嘌呤 、 1-己炔 在 copper(l) iodide 、 四(三苯基膦)钯 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以77%的产率得到9-benzyl-6-(hex-1-yn-1-yl)purine
  参考文献：
  名称：

  Covalent Analogues of DNA Base-Pairs and Triplets IV. Synthesis of Trisubstituted Benzenes Bearing Purine and/or Pyrimidine Rings by Cyclotrimerization of 6-Ethynylpurines and/or 5-Ethynyl-1,3-dimethyluracil

  摘要：

  Ni催化的6-乙炔基嘌呤（3）或5-乙炔基-1,3-二甲基尿嘧啶（4）的环三聚反应生成了1,2,4-三（嘌呤-6-基）苯（7）或1,2,4-三（1,3-二甲基尿嘧啶-5-基）苯（9）。对称的1,3,5-三（嘌呤-6-基）苯（8）作为副产物以极低的收率形式存在。9-苄基-6-乙炔基嘌呤（3a）与4的共环三聚反应生成了三（嘌呤基）苯（7a）作为主要产物，还伴随着1,2-双（9-苄基嘌呤-6-基）-4-（1,3-二甲基尿嘧啶-5-基）苯（10）和其他衍生物和异构体的复杂混合物。化合物7-10是Hoogsteen碱基三联体的类似物。

  DOI：

  10.1135/cccc20021223

文献信息

• Novel Method for Preparation of Highly Substituted 6-Arylpurines by Reactions of 6-Alkynylpurines with Zirconacyclopentadienes
  作者：Pavel Turek、Martin Kotora、Michal Hocek、Ivan Votruba

  DOI：10.1135/cccc20050339

  日期：——

  Reactions of various zirconacyclopentadienes bearing alkyl and aryl groups with 6-alkynylpurines in the presence of NiBr₂(PPh₃)₂ afforded the corresponding 6-arylpurines with highly hydrophobic aryl moieties in low to moderate yields. Some of the title purines showed interesting cytostatic activity.

  在NiBr₂(PPh₃)₂的存在下，带有烷基和芳基的各种锆茂环戊二烯与6-炔基嘌呤反应，得到了相应的6-芳基嘌呤，其芳基部分具有高度疏水性，收率低至中等。其中一些嘌呤表现出有趣的细胞毒抑制活性。
• [2+2+2]-Co-cyclotrimerization 6-alkynylpurines with diynes: a method for preparation of 6-arylpurines
  作者：Pavel Turek、Martin Kotora、Michal Hocek、Ivana Cı́sařová

  DOI：10.1016/s0040-4039(02)02643-6

  日期：2003.1

  A novel approach to 6-arylpurines based on [2+2+2]-co-cyclotrimerization of 6-alkynylpurines with various alpha,omega-diynes is described. Co-cyclotrimerization is catalyzed by Ni- and Co-phosphine catalysts and their choice depends on the substitution pattern of the both reactants. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Cocyclotrimerization of 6-Alkynylpurines with α,ω-Diynes as a Novel Approach to Biologically Active 6-Arylpurines
  作者：Pavel Turek、Martin Kotora、Iva Tišlerová、Michal Hocek、Ivan Votruba、Ivana Císařová

  DOI：10.1021/jo0486342

  日期：2004.12.1

  Transition metal complex catalyzed cocyclotrimerization of 6-alkynylpurines 1 with various diynes enables the preparation of a plethora of substituted 6-arylpurines 3 in good yields. The most general catalyst for the reaction is a user-friendly system based on a nickel-phosphine complex and reductant (NiBr2(dppe)/Zn) in MeCN. The reaction conditions are compatible with various protective groups on the purine moiety (Bn, THP). As far as other potential catalysts were concerned, only CoBr(PPh3)(3) showed reasonable activity in cocyclotrimerization of alkynylpurines with dipropargyl ether. A comparison of catalytic with stoichiometric approaches and the ligand effect in the catalyst is also given. Cytostatic activity screening of title 6-arylpurines was performed and several moderately active compounds were found.
• Covalent Analogues of DNA Base-Pairs and Triplets IV. Synthesis of Trisubstituted Benzenes Bearing Purine and/or Pyrimidine Rings by Cyclotrimerization of 6-Ethynylpurines and/or 5-Ethynyl-1,3-dimethyluracil
  作者：Michal Hocek、Irena G. Stará、Ivo Starý、Hana Dvořáková

  DOI：10.1135/cccc20021223

  日期：——

  Ni-Catalyzed cyclotrimerizations of 6-ethynylpurines 3 or 5-ethynyl-1,3-dimethyluracil (4) afforded the 1,2,4-tris(purin-6-yl)benzenes 7 or 1,2,4-tris(1,3-dimetyhyluracil-5-yl)benzene (9), respectively. The symmetrical 1,3,5-tris(purin-6-yl)benzenes 8 were also formed as minor products in very low yields. Co-cyclotrimerization of 9-benzyl-6-ethynylpurine (3a) with 4 afforded the tris(purinyl)benzene 7a as a major product along with 1,2-bis(9-benzylpurin-6-yl)-4-(1,3-dimethyluracil-5-yl)benzene (10) and a complex mixture of other derivatives and isomers. Compounds 7-10 are analogues of Hoogsteen base-triplets.

  Ni催化的6-乙炔基嘌呤（3）或5-乙炔基-1,3-二甲基尿嘧啶（4）的环三聚反应生成了1,2,4-三（嘌呤-6-基）苯（7）或1,2,4-三（1,3-二甲基尿嘧啶-5-基）苯（9）。对称的1,3,5-三（嘌呤-6-基）苯（8）作为副产物以极低的收率形式存在。9-苄基-6-乙炔基嘌呤（3a）与4的共环三聚反应生成了三（嘌呤基）苯（7a）作为主要产物，还伴随着1,2-双（9-苄基嘌呤-6-基）-4-（1,3-二甲基尿嘧啶-5-基）苯（10）和其他衍生物和异构体的复杂混合物。化合物7-10是Hoogsteen碱基三联体的类似物。