(1S,12S)-15-methoxy-16-phenylmethoxy-20-propyl-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaene | 180890-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (1S,12S)-15-methoxy-16-phenylmethoxy-20-propyl-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaene
• CAS: 180890-76-0
• 化学式: C₂₈H₂₉NO₄
• 分子量: 443.543
• InChiKey: GAJHXQFKQXNLGE-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,12S)-15-methoxy-16-phenylmethoxy-20-propyl-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以70%的产率得到N-propylnorcaryachine
  参考文献：
  名称：

  Preparation of N-Alkylnorpavines via Competitive N-Dealkylation of Quaternary Pavines

  摘要：

  N-Alkyl quaternary pavine salts were converted into N-alkyl tertiary pavines by refluxing ethanolamine, via a competitive N-dealkylation mechanism. The following N-dealkylation order was observed: benzyl > allyl > Me > Et > Pr-n greater than or equal to (n)Bu. Further study indicated that N-alkyl- and N-acylpavines could be obtained from N-methyl tertiary pavines in a one-pot reaction (acid anhydride/allyl bromide or alkyl halide, reflux). This finding provides an alternative method for preparing N-alkyl tertiary pavines.

  DOI：

  10.3987/com-96-7400
• 作为产物：
  描述：

  caryachine N-methoperchlorate 在 potassium carbonate 、 C.I.酸性橙108 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 (1S,12S)-15-methoxy-16-phenylmethoxy-20-propyl-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaene
  参考文献：
  名称：

  Preparation of N-Alkylnorpavines via Competitive N-Dealkylation of Quaternary Pavines

  摘要：

  N-Alkyl quaternary pavine salts were converted into N-alkyl tertiary pavines by refluxing ethanolamine, via a competitive N-dealkylation mechanism. The following N-dealkylation order was observed: benzyl > allyl > Me > Et > Pr-n greater than or equal to (n)Bu. Further study indicated that N-alkyl- and N-acylpavines could be obtained from N-methyl tertiary pavines in a one-pot reaction (acid anhydride/allyl bromide or alkyl halide, reflux). This finding provides an alternative method for preparing N-alkyl tertiary pavines.

  DOI：

  10.3987/com-96-7400