7-(3-Bromo-3-methyl-butyl)-1,7-dihydro-purin-6-one O-benzyl-oxime | 827585-39-7

• 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: 7-(3-Bromo-3-methyl-butyl)-1,7-dihydro-purin-6-one O-benzyl-oxime
• 英文别名: 7-(3-bromo-3-methylbutyl)-N-phenylmethoxypurin-6-amine
• CAS: 827585-39-7
• 化学式: C₁₇H₂₀BrN₅O
• 分子量: 390.283
• InChiKey: ORSFDAPQNULCAP-UHFFFAOYSA-N

物化性质

• 沸点：
  565.0±60.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(3-Bromo-3-methyl-butyl)-1,7-dihydro-purin-6-one O-benzyl-oxime 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以95%的产率得到7,8,9,10-tetrahydro-10-hydroxy-9,9-dimethyl[1,4]diazepino[1,2,3-g,h]purine
  参考文献：
  名称：

  Synthesis of 9-Substituted Tetrahydrodiazepinopurines:  Studies toward the Total Synthesis of Asmarines

  摘要：

  A methodology for the preparation of asmarine analogues has been developed. The asmarines are cytotoxic marine alkaloids with a unique tetrahydro[1,4]diazepino[1,2,3-g,h]purine (THDAP) structure. Three cyclization methods were applied for the preparation of the 9,9-disubstituted 10-hydroxy-THDAP system, namely, aminomercurization, iodocyclization, and acid-catalyzed cyclization. The DMPM group of the NOH functionality and cyanoethyl group of the N-9 atom were found to be the most suitable protecting groups. The structures of all compounds were mainly determined from NMR measurements including N-15 chemical shifts obtained from (NH)-N-15 HMBC spectra. The end products are at least about 1 order of magnitude less active than the natural product asmarine B.

  DOI：

  10.1021/jo048622g
• 作为产物：
  描述：

  9-Benzhydryl-6-[(Z)-benzyloxyimino]-7-(3-methyl-but-2-enyl)-6,9-dihydro-1H-purin-7-ium; bromide 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以72%的产率得到7-(3-Bromo-3-methyl-butyl)-1,7-dihydro-purin-6-one O-benzyl-oxime
  参考文献：
  名称：

  Synthesis of 9-Substituted Tetrahydrodiazepinopurines:  Studies toward the Total Synthesis of Asmarines

  摘要：

  A methodology for the preparation of asmarine analogues has been developed. The asmarines are cytotoxic marine alkaloids with a unique tetrahydro[1,4]diazepino[1,2,3-g,h]purine (THDAP) structure. Three cyclization methods were applied for the preparation of the 9,9-disubstituted 10-hydroxy-THDAP system, namely, aminomercurization, iodocyclization, and acid-catalyzed cyclization. The DMPM group of the NOH functionality and cyanoethyl group of the N-9 atom were found to be the most suitable protecting groups. The structures of all compounds were mainly determined from NMR measurements including N-15 chemical shifts obtained from (NH)-N-15 HMBC spectra. The end products are at least about 1 order of magnitude less active than the natural product asmarine B.

  DOI：

  10.1021/jo048622g