N-phenyl-9-prop-2-enylpurin-6-amine | 1393886-19-5

• 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: N-phenyl-9-prop-2-enylpurin-6-amine
• CAS: 1393886-19-5
• 化学式: C₁₄H₁₃N₅
• 分子量: 251.291
• InChiKey: FNZJFOHCLQQDFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-phenyl-9-prop-2-enylpurin-6-amine 在 碘苯二乙酸 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 反应 2.0h， 以80%的产率得到3-allyl-3H-benzo[4,5]imidazo[2,1-i]purine
  参考文献：
  名称：

  Copper-Catalyzed Synthesis of Purine-Fused Polycyclics

  摘要：

  A novel protocol for a Cu-catalyzed direct C-(sp2)-H activation/intramolecular amination reaction of 6-anilinopurine nucleosides has been developed. This approach provides a new access to a variety of multiheterocyclic compounds from purine compounds via Cu-catalyzed intramolecular N-H bond tautomerism which are endowed with fluorescence.

  DOI：

  10.1021/ol301848v
• 作为产物：
  描述：

  9-allyl-6-chloro-9H-purine 、 苯胺 以 乙醇 为溶剂， 反应 6.0h， 生成 N-phenyl-9-prop-2-enylpurin-6-amine
  参考文献：
  名称：

  Copper-Catalyzed Synthesis of Purine-Fused Polycyclics

  摘要：

  A novel protocol for a Cu-catalyzed direct C-(sp2)-H activation/intramolecular amination reaction of 6-anilinopurine nucleosides has been developed. This approach provides a new access to a variety of multiheterocyclic compounds from purine compounds via Cu-catalyzed intramolecular N-H bond tautomerism which are endowed with fluorescence.

  DOI：

  10.1021/ol301848v

文献信息

• Ruthenium-Catalyzed Oxidative Annulation of 6-Anilinopurines with Alkynes<i>via</i>CH Activation: Synthesis of Indole-Substituted Purines/Purine Nucleosides
  作者：Srinivasarao Allu、K. C. Kumara Swamy

  DOI：10.1002/adsc.201500314

  日期：2015.8.24

  Indole‐substituted purine nucleobases have been synthesized by Ru‐catalyzed oxidative annulation of 6‐anilinopurines with internal alkynes that involves CH activation. Unsymmetrical aryl(alkyl)alkynes led to high regioselectivity. The reaction was also successful with nucleosides by delivering unprotected indole‐substituted nucleosides. In the presence of [RuCl2(p‐cymene)]2 and copper(II) acetate

  吲哚取代的嘌呤核苷碱基是通过Ru-催化的6-苯胺嘌呤与内部炔烃的氧化an合反应而合成的，其中炔烃涉及CH活化。不对称的芳基（烷基）炔烃导致高区域选择性。通过递送未保护的吲哚取代的核苷，该反应也与核苷成功进行了反应。在将[RuCl存在2（p -cymene）] 2和铜（II），乙酸水合物[铜（OAC）2 ⋅H 2 O]，在一些情况下，我们观察到两倍Ç  ħ活化具有荧光的产品。钌环中间体的结晶学特征表明，嘌呤的N-1氮原子可作为本转化的指导基团。
• Copper-Catalyzed Synthesis of Purine-Fused Polycyclics
  作者：Gui-Rong Qu、Lei Liang、Hong-Ying Niu、Wei-Hao Rao、Hai-Ming Guo、John S. Fossey

  DOI：10.1021/ol301848v

  日期：2012.9.7

  A novel protocol for a Cu-catalyzed direct C-(sp2)-H activation/intramolecular amination reaction of 6-anilinopurine nucleosides has been developed. This approach provides a new access to a variety of multiheterocyclic compounds from purine compounds via Cu-catalyzed intramolecular N-H bond tautomerism which are endowed with fluorescence.