2-(6-amino-purin-9-yl)-1-thiophen-3-yl-ethanone | 1254704-53-4

• 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: 2-(6-amino-purin-9-yl)-1-thiophen-3-yl-ethanone
• 英文别名: 2-(6-Aminopurin-9-yl)-1-thiophen-3-ylethanone；2-(6-aminopurin-9-yl)-1-thiophen-3-ylethanone
• CAS: 1254704-53-4
• 化学式: C₁₁H₉N₅OS
• 分子量: 259.291
• InChiKey: JNWYZVJGSZDSMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-溴乙酰基噻吩 、 腺嘌呤 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以68%的产率得到2-(6-amino-purin-9-yl)-1-thiophen-3-yl-ethanone
  参考文献：
  名称：

  Synthesis and characterization of nucleobase functionalized monothiophenes

  摘要：

  The synthesis of a series of nucleobase functionalized thiophene monomers has been accomplished through the reaction of 2-bromo-1-thiophen-3-yl-ethanone with the corresponding DNA base anion. The distinctive pK(a) values for the various amine groups in the nucleobases provided a pathway for the creation of specific anions through selective deprotonation of these groups. Using the appropriate anion it is possible to create an amine linkage between the thiophene and nucleobase that is, analogous to that found between the deoxyribose sugar and nucleobase, in the biologically occurring nucleoside. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.034

文献信息

• Synthesis and characterization of nucleobase functionalized monothiophenes
  作者：Christopher D. McTiernan、M’hamed Chahma

  DOI：10.1016/j.tetlet.2010.08.034

  日期：2010.10

  The synthesis of a series of nucleobase functionalized thiophene monomers has been accomplished through the reaction of 2-bromo-1-thiophen-3-yl-ethanone with the corresponding DNA base anion. The distinctive pK(a) values for the various amine groups in the nucleobases provided a pathway for the creation of specific anions through selective deprotonation of these groups. Using the appropriate anion it is possible to create an amine linkage between the thiophene and nucleobase that is, analogous to that found between the deoxyribose sugar and nucleobase, in the biologically occurring nucleoside. (C) 2010 Elsevier Ltd. All rights reserved.