5-(1-adamantyl)-1-bromo-3-methylpent-2-ene | 827585-02-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 5-(1-adamantyl)-1-bromo-3-methylpent-2-ene
• 英文别名: 1-(5-bromo-3-methylpent-3-enyl)adamantane
• CAS: 827585-02-4
• 化学式: C₁₆H₂₅Br
• 分子量: 297.279
• InChiKey: UDPQWDZYKHUZLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  5-(1-adamantyl)-1-bromo-3-methylpent-2-ene 在 氢溴酸 、 potassium carbonate 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 7,8,9,10-tetrahydro-9-(2-(1-adamantyl)ethyl)-10-hydroxy-9-methyl[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：

  5-(1-adamantyl)-3-methyl-1-penten-3-ol 在 氢溴酸 作用下， 以 Petroleum ether 为溶剂， 反应 1.0h， 以80%的产率得到5-(1-adamantyl)-1-bromo-3-methylpent-2-ene
  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