7,8,9,10-tetrahydro-10-benzyloxy-9-phenethyl-[1,4]diazepino[1,2,3-g,h]purine | 827585-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 嘧啶二氮卓类
• 英文名称: 7,8,9,10-tetrahydro-10-benzyloxy-9-phenethyl-[1,4]diazepino[1,2,3-g,h]purine
• 英文别名: 10-(2-Phenylethyl)-9-phenylmethoxy-1,3,5,7,9-pentazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7-tetraene
• CAS: 827585-12-6
• 化学式: C₂₃H₂₃N₅O
• 分子量: 385.469
• InChiKey: KXWQHFLGHXHFEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  56.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7,8,9,10-tetrahydro-10-benzyloxy-9-phenethyl-[1,4]diazepino[1,2,3-g,h]purine 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.5h， 以74%的产率得到7,8,9,10-tetrahydro-10-hydroxy-9-phenethyl-[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-hydroxy-5-phenyl-pentyl)-6,9-dihydro-1H-purin-7-ium; bromide 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 7,8,9,10-tetrahydro-10-benzyloxy-9-phenethyl-[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

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.