5-(1-adamantyl)-3-methyl-1-penten-3-ol | 827584-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(1-adamantyl)-3-methyl-1-penten-3-ol
• 英文别名: 5-(1-Adamantyl)-3-methylpent-1-en-3-ol
• CAS: 827584-99-6
• 化学式: C₁₆H₂₆O
• 分子量: 234.382
• InChiKey: KJZUPMDJKCPCBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(1-adamantyl)-3-methyl-1-penten-3-ol 在 氢溴酸 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 Petroleum ether 为溶剂， 反应 74.0h， 生成 7-[5-(1-adamantyl)-3-methylpent-2-enyl]-N-[(3,4-dimethoxyphenyl)methoxy]purin-6-amine
  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：

  1-(2-溴乙基)金刚烷 在 正丁基锂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 水 、 乙腈 为溶剂， 反应 3.16h， 生成 5-(1-adamantyl)-3-methyl-1-penten-3-ol
  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

文献信息

• Synthesis of 9-Substituted Tetrahydrodiazepinopurines:  Studies toward the Total Synthesis of Asmarines
  作者：Doron Pappo、Shiri Shimony、Yoel Kashman

  DOI：10.1021/jo048622g

  日期：2005.1.1

  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.