2-碘-9-(四氢吡喃-2-基)腺嘌呤 | 1195939-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-碘-9-(四氢吡喃-2-基)腺嘌呤
• 英文名称: 2-iodo-9-(tetrahydropyran-2-yl)adenine
• 英文别名: 2-Iodo-9-(oxan-2-yl)purin-6-amine
• CAS: 1195939-15-1
• 化学式: C₁₀H₁₂IN₅O
• 分子量: 345.143
• InChiKey: KOAKOXYDPRYZTK-UHFFFAOYSA-N

物化性质

• 熔点：
  209-210 °C
• 沸点：
  585.5±60.0 °C(Predicted)
• 密度：
  2.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-碘-9-(四氢吡喃-2-基)腺嘌呤 在 水 、 copper dichloride 作用下， 以 乙醇 为溶剂， 以89%的产率得到2-碘-6-氨基嘌呤
  参考文献：
  名称：

  Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides

  摘要：

  Herein we report both linear and convergent pathways for the preparation of 2-alkynyl substituted adenosine-5'-N-ethylcarboxamides via the versatile synthetic intermediate, 2-iodoadenosine-5'-N-ethylcarboxamide (13). The linear approach afforded 13 in an overall yield of 30% from guanosine over eight synthetic steps. The convergent approach was shorter, but proceeded in lower yield (five steps, 20% yield). Both approaches compare favourably with previously reported syntheses of 13, which has been prepared in 15% yield from guanosine over nine steps. 2-Iodoadenosine-5'-N-ethylcarboxamide (13) was subsequently converted to HENECA (2) and PHPNECA (3) to exemplify the utility of this approach for the preparation of potent A(2A) adenosine receptor agonists. The linear approach was also amenable to the synthesis of 2-fluoropurine ribosides, which were subsequently elaborated into 2-alkylaminoadenosine-5'-N-ethylcarboxamides. Furthermore, both of these synthetic approaches are readily amenable to the synthesis of adenosine analogues with varied 2-, 6- and 5'-substitution patterns. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.057
• 作为产物：
  描述：

  6-chloro-2-iodo-9-(tetrahydropyran-2-yl)purine 在 氨 作用下， 以 甲醇 为溶剂， 反应 168.0h， 以90%的产率得到2-碘-9-(四氢吡喃-2-基)腺嘌呤
  参考文献：
  名称：

  Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides

  摘要：

  Herein we report both linear and convergent pathways for the preparation of 2-alkynyl substituted adenosine-5'-N-ethylcarboxamides via the versatile synthetic intermediate, 2-iodoadenosine-5'-N-ethylcarboxamide (13). The linear approach afforded 13 in an overall yield of 30% from guanosine over eight synthetic steps. The convergent approach was shorter, but proceeded in lower yield (five steps, 20% yield). Both approaches compare favourably with previously reported syntheses of 13, which has been prepared in 15% yield from guanosine over nine steps. 2-Iodoadenosine-5'-N-ethylcarboxamide (13) was subsequently converted to HENECA (2) and PHPNECA (3) to exemplify the utility of this approach for the preparation of potent A(2A) adenosine receptor agonists. The linear approach was also amenable to the synthesis of 2-fluoropurine ribosides, which were subsequently elaborated into 2-alkylaminoadenosine-5'-N-ethylcarboxamides. Furthermore, both of these synthetic approaches are readily amenable to the synthesis of adenosine analogues with varied 2-, 6- and 5'-substitution patterns. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.057