6-(Hex-1-yn-1-yl)-9-(oxan-2-yl)-9H-purine | 819877-83-3

• 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: 6-(Hex-1-yn-1-yl)-9-(oxan-2-yl)-9H-purine
• 英文别名: 6-hex-1-ynyl-9-(oxan-2-yl)purine
• CAS: 819877-83-3
• 化学式: C₁₆H₂₀N₄O
• 分子量: 284.361
• InChiKey: IFQZVXZMUCUNPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  6-(Hex-1-yn-1-yl)-9-(oxan-2-yl)-9H-purine 、 2,2-二丙炔基丙二酸二乙酯 在 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 、 锌 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以58%的产率得到Diethyl 5-butyl-6-[9-(oxan-2-yl)purin-6-yl]-1,3-dihydroindene-2,2-dicarboxylate
  参考文献：
  名称：

  Cocyclotrimerization of 6-Alkynylpurines with α,ω-Diynes as a Novel Approach to Biologically Active 6-Arylpurines

  摘要：

  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.

  DOI：

  10.1021/jo0486342

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。
• 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.