2-amino-8-bromo-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one compound with 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (1:1) | 1357158-20-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-amino-8-bromo-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one compound with 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (1:1)
• CAS: 1357158-20-3
• 化学式: C₉H₁₆N₂*C₁₀H₁₂BrN₅O₅
• 分子量: 514.379
• InChiKey: LIRRURNBRJQNRM-YEOHUATISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  32.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  175.11
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 8-溴鸟苷 以 甲醇 为溶剂， 以62%的产率得到2-amino-8-bromo-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one compound with 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (1:1)
  参考文献：
  名称：

  DBU induced formation of 8-bromoguanosine dimer with three hydrogen bonds between the GG− base pairs

  摘要：

  Upon hemideprotonation of 8-bromoguanosine (8-BrG) at the N1 position, induced by DBU, the adduct [8-BrG][8-BrG](-)[DBU-H](+) was formed. Slow evaporation of the 8-BrG methanol solution, in the presence of 0.5 equiv of DBU, yielded two polymorphic structures (1 and 2), where a neutral [8-BrG] (A) and N1 deprotonated, anionic 8-bromoguanosine [8-BrG](-) (B) were joined together through three intermolecular hydrogen bonds involving O6, N1 and C2-NH2 sites. Such pairing gave planar GG(-) dimers as the basic motif of crystal packing in both polymorphs. Both neutral and deprotonated guanosine molecules in the structure of 1 had the ribose units in a syn conformation. In the structure of polymorph 2, the N1 deprotonated guanosine molecule (B) retained the syn glycosidic conformation, while the nondeprotonated guanosine molecule (A) adopted the natural and conformation of the ribose unit with respect to the nucleobase. Ribose rings revealed different puckering; only those of deprotonated molecules 1B and 2B possessed the usual C2'-endo envelope conformation. Crystal packing in both structures was guided by the highly complex H-bonded pattern. The CSD was searched for related structures, which are discussed with reference to polymorphs 1 and 2. H-1 and C-13 NMR spectroscopic evidence is provided showing that the three H-bonded adduct [8-BrG][8-BrG](-)[DBU H](+) was also formed in the highly H-bond competitive DMSO solution. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.11.086