6-chloro-9-(propa-1,2-dien-1-yl)-9H-purine | 1538583-95-7

• 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: 6-chloro-9-(propa-1,2-dien-1-yl)-9H-purine
• 英文别名: N⁹-propadienyl-6-chloropurine
• CAS: 1538583-95-7
• 化学式: C₈H₅ClN₄
• 分子量: 192.607
• InChiKey: VSHMZGSCGPTTAH-UHFFFAOYSA-N

物化性质

• 沸点：
  396.1±45.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-chloro-9-(propa-1,2-dien-1-yl)-9H-purine 、 溶剂黄146 在 silver carbonate 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以89%的产率得到(E)-3-(6-chloro-9H-purin-9-yl)allyl acetate
  参考文献：
  名称：

  A New Strategy To Construct Acyclic Nucleosides via Ag(I)-Catalyzed Addition of Pronucleophiles to 9-Allenyl-9H-purines

  摘要：

  A new strategy to construct acyclic nucleosides with diverse side chains was developed. With Ag(I) salts as catalysts, the hydrocarboxylation, hydroamination, and hydrocarbonation reactions proceeded well, affording acyclic nucleosides in good yields (41 examples, 60-98% yields). Meanwhile, these reactions exhibited high chemoselectivities and E-selectivities.

  DOI：

  10.1021/ol4036566
• 作为产物：
  描述：

  6-chloro-9-(prop-2-yn-1-yl)-9H-purine 在 sodium t-butanolate 作用下， 以 二氯甲烷 为溶剂， 生成 6-chloro-9-(propa-1,2-dien-1-yl)-9H-purine
  参考文献：
  名称：

  A New Strategy To Construct Acyclic Nucleosides via Ag(I)-Catalyzed Addition of Pronucleophiles to 9-Allenyl-9H-purines

  摘要：

  A new strategy to construct acyclic nucleosides with diverse side chains was developed. With Ag(I) salts as catalysts, the hydrocarboxylation, hydroamination, and hydrocarbonation reactions proceeded well, affording acyclic nucleosides in good yields (41 examples, 60-98% yields). Meanwhile, these reactions exhibited high chemoselectivities and E-selectivities.

  DOI：

  10.1021/ol4036566

文献信息

• Regiodivergent Synthesis of Pyrazolines with a Quaternary Carbon Center via Cycloaddition of Diazoesters to <i>N</i>-Purine-Substituted Allenes
  作者：Ming-Sheng Xie、Zhen Guo、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/acs.orglett.8b02161

  日期：2018.8.17

  Diversity-oriented synthesis of pyrazoline derivatives that contain a quaternary carbon center has been achieved via the 1,3-dipolar cycloaddition between N-purine-substituted allenes and α-alkyl/aryl diazoesters. Using Pd2(dba)3 as a catalyst, only 1-pyrazoline derivatives are produced in a regioselective manner. When DPPB is used as a catalyst, diverse 1-pyrazolines and 2-pyrazolines are obtained

  通过N-嘌呤取代的烯与α-烷基/芳基重氮酸酯之间的1，3-偶极环加成反应，实现了包含季碳中心的吡唑啉衍生物的多样性导向合成。使用Pd 2（dba）3作为催化剂，以区域选择性方式仅产生1-吡唑啉衍生物。当DPPB用作催化剂时，以中等至良好的总收率获得了不同的1-吡唑啉和2-吡唑啉。
• Expeditious synthesis of 9-allenylpurines <i>via</i> cesium carbonate catalyzed isomerization of 9-alkynylpurines
  作者：Mingwu Yu、Xiguang Liu、Qingsong Jiang、Hongguang Du

  DOI：10.1080/10426507.2018.1436547

  日期：2018.7.3

  An expeditious and convenient method to synthesize 9-allenylpurines via cesium carbonate catalyzed isomerization of 9-alkynylpurines has been successfully developed. The reactions proceeded rapidly under the base conditions and formed the desired products in good to excellent yields. The method was suitable with a broad substrate scope and proceeded well even on a multgram-scale. The obtained 9-allenylpurines were successfully applied to prepare various potential bioactive 9-acyclic nucleosides with high regioselectivity promoted by AgNO3.[GRAPHICS].