O-acetylcaryachine | 180890-77-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: O-acetylcaryachine
• 英文别名: [(1S,12S)-15-methoxy-20-methyl-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaen-16-yl] acetate
• CAS: 180890-77-1
• 化学式: C₂₁H₂₁NO₅
• 分子量: 367.401
• InChiKey: BRYWXNQXMLXTOV-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-溴丙烯 、 O-acetylcaryachine 以 xylene 为溶剂， 反应 24.0h， 以42%的产率得到[(1S,12S)-15-methoxy-20-prop-2-enyl-5,7-dioxa-20-azapentacyclo[10.7.1.02,10.04,8.013,18]icosa-2,4(8),9,13,15,17-hexaen-16-yl] acetate
  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：

  乙酸酐 、 以 xylene 为溶剂， 反应 96.0h， 以74.8%的产率得到O-acetylcaryachine
  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