(5R,6R,7R,9R,13S,14S)-7-acetyl-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-6,14-ethenomorphinane | 162062-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (5R,6R,7R,9R,13S,14S)-7-acetyl-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-6,14-ethenomorphinane
• 英文别名: 1-[(5a,7b)-4,5-Epoxy-18,19-dihydro-3,6-dimethoxy-6,14-ethenomorphinan-7-yl]-ethanone；1-[(1S,2S,6R,14R,15R,16R)-11,15-dimethoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-16-yl]ethanone
• CAS: 162062-77-3
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: UNVQSICIFOAIAH-CYTOHMRRSA-N

物化性质

• 沸点：
  528.1±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)
• 溶解度：
  溶于丙酮、氯仿、DCM

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-溴丙烯 、 (5R,6R,7R,9R,13S,14S)-7-acetyl-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-6,14-ethenomorphinane 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以46%的产率得到1-[(1S,2S,6R,14R,15R,16R)-11,15-dimethoxy-5-prop-2-enyl-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-16-yl]ethanone
  参考文献：
  名称：

  Synthesis of N-Substituted 7β-Diprenorphine Derivatives

  摘要：

  The separation of thevinone (2a) and beta-thevinone (2b), as well as that of dihydrothevinone (3a) and beta-dihydrothevinone (3b) was accomplished. By the application of various procedures numerous new N-substituted Diprenorphine analogues (8a-f) with 7R absolute configuration were synthesized. Detailed pharmacological investigation of the prepared compounds may contribute to a better understanding of the structure-activity relationship of morphine alkaloids.

  DOI：

  10.1080/00397919508013419
• 作为产物：
  描述：

  7α-acetyl-6,14-endoethanotetrahydrothebaine 在 吡啶盐酸盐 、 偶氮二甲酸二乙酯 作用下， 生成 (5R,6R,7R,9R,13S,14S)-7-acetyl-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-6,14-ethenomorphinane
  参考文献：
  名称：

  Synthesis of N-Substituted 7β-Diprenorphine Derivatives

  摘要：

  The separation of thevinone (2a) and beta-thevinone (2b), as well as that of dihydrothevinone (3a) and beta-dihydrothevinone (3b) was accomplished. By the application of various procedures numerous new N-substituted Diprenorphine analogues (8a-f) with 7R absolute configuration were synthesized. Detailed pharmacological investigation of the prepared compounds may contribute to a better understanding of the structure-activity relationship of morphine alkaloids.

  DOI：

  10.1080/00397919508013419

文献信息

• Synthesis of N-Substituted 7β-Diprenorphine Derivatives
  作者：János Marton、Szilárd Miklòs、Sàndor Hosztafi、Sándor Makleit

  DOI：10.1080/00397919508013419

  日期：1995.3

  The separation of thevinone (2a) and beta-thevinone (2b), as well as that of dihydrothevinone (3a) and beta-dihydrothevinone (3b) was accomplished. By the application of various procedures numerous new N-substituted Diprenorphine analogues (8a-f) with 7R absolute configuration were synthesized. Detailed pharmacological investigation of the prepared compounds may contribute to a better understanding of the structure-activity relationship of morphine alkaloids.