N-[(3,4-dimethoxyphenyl)methoxy]-7-(3-methylbut-2-enyl)purin-6-amine | 827585-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(3,4-dimethoxyphenyl)methoxy]-7-(3-methylbut-2-enyl)purin-6-amine
• CAS: 827585-36-4
• 化学式: C₁₉H₂₃N₅O₃
• 分子量: 369.423
• InChiKey: UXHVNWOUEPVARC-UHFFFAOYSA-N

物化性质

• 沸点：
  577.1±60.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(3,4-dimethoxyphenyl)methoxy]-7-(3-methylbut-2-enyl)purin-6-amine 在 mercury(II) diacetate 、 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.33h， 以57%的产率得到7,8,9,10-tetrahydro-10-(3,4-dimethoxybenzyloxy)-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：

  3-(6-chloro-9H-purin-9-yl)propanenitrile 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 N-[(3,4-dimethoxyphenyl)methoxy]-7-(3-methylbut-2-enyl)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

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.