N⁹-allenyladenine

• 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: N⁹-allenyladenine
• 英文别名: 9-(propa-1,2-dien-1-yl)-9H-purin-6-amine；N⁹-propadienyl-6-aminopurine；9-allenyl-9H-adenine；9-propa-1,2-dienylpurin-6-amine
• 化学式: C₈H₇N₅
• 分子量: 173.177
• InChiKey: BGLVIXKCDJHLGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 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：
  69.62
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N-9-propargyladenine 在 caesium carbonate 作用下， 以 丙醇 为溶剂， 反应 0.25h， 以85%的产率得到N⁹-allenyladenine
  参考文献：
  名称：

  Expeditious synthesis of 9-allenylpurines via cesium carbonate catalyzed isomerization of 9-alkynylpurines

  摘要：

  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].

  DOI：

  10.1080/10426507.2018.1436547

文献信息

• A New Strategy To Construct Acyclic Nucleosides via Ag(I)-Catalyzed Addition of Pronucleophiles to 9-Allenyl-9<i>H</i>-purines
  作者：Tao Wei、Ming-Sheng Xie、Gui-Rong Qu、Hong-Ying Niu、Hai-Ming Guo

  DOI：10.1021/ol4036566

  日期：2014.2.7

  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.
• Alkylation of adenine with t-propargyl chlorides: acetylene/allene ratio and N9/N7 regioselectivity
  作者：Ramachandra V. Joshi、Jiri Zemlicka

  DOI：10.1016/s0040-4020(01)86315-8

  日期：1993.3

  Alkylation of adenine ( 6) with dialkylpropargyl chlorides 3a and 3b gave N9- and N7-acetylenes 7a, 7b and 9a, 9b accompanied by N9-allenes 8a, 8b. Bromoallene 10a gave only 7a and 7b but no allene 8a. Reaction of propargyl chloride with 6 led only to N9-propargyladenine (7c) whereas chloroallene 10b afforded 7c and allene 8c. The possible reaction course will be discussed with emphasis on the influences of structure, reagent and solvent on acetylene/allene ratio and N9/N7 regioselectivity of alkylation. The nonequivalent methylene groups of 7b and 9b have DELTAdelta 0.67 and 1.07, respectively, appearing as sextets in the H-1 NMR spectra.
• [3,3] Sigmatropic Rearrangement of 3-Alkynyladenines.
  作者：Lajos Kovács、Gábor Kiss、Péter Benke、Gabriella Pócsfalvi、Inge L. Møller、Ruby I. Nielsen、Carl Erik Olsen、Connie N. Rosendahl、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0466

  日期：——
• 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].

表征谱图