1-(3-ethoxycarbonyloxy-4-methoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline | 861328-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(3-ethoxycarbonyloxy-4-methoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline
• 英文别名: 1-(3-Aethoxycarbonyloxy-4-methoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isochinolin
• CAS: 861328-28-1
• 化学式: C₂₂H₂₅NO₆
• 分子量: 399.444
• InChiKey: QHGOYLFRSAHXOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.58
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(3-ethoxycarbonyloxy-4-methoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Biotransformation of Phenolic Tetrahydroprotoberberines in Plant Cell Cultures Followed by LC-NMR, LC-MS, and LC-CD

  摘要：

  A metabolic pathway of 2,3,10,11-oxygenated tetrahydroprotoberberines having the OH group on ring D was demonstrated. Metabolism of (13)C- or D(2)-labeled precursors was studied in cell cultures of Macleaya, Corydalis, and Nandina species. The structures of alkaloid metabolites obtained from feeding experiments were determined by application of combined LC-NMR, LC-MS/MS, and LC-CD techniques. (S)-Tetrahydropseudoprotoberberine (5) was stereospecifically O-methylated to the S-isomer (12) in cell cultures of three plants species. This S-isomer was further N-methylated to the (S)-alpha-N-methyl salt (15), which was oxidized to produce the pseudoprotopine-type alkaloid (10) in cell cultures of Macleaya and Corydalis species. These transformations were the same as those of 2,3,9,10-oxygenated protoberberines. The tetrahydropseudoprotoberberines (5, 6, and 12) were dehydrogenated to pseudoprotoberberines (13, 16, and 14), respectively. Both the R- and S-enantiomers of 5 were dehydrogenated in Macleaya cordata different from the case of 2,3,9,10-oxygenated protoberberines. Precursor 7, with OH groups at C-10 and C-11, was O-methylated at C-10 in M. cordata and C. ochotensis var. raddeana, which was distinct from O-methylation in N. domestica, in which 7 was O-methylated at both C-11 and C-10. Stereoselective O-demethylation [(S)-5 to (S)-18] occurred in N. domestica.

  DOI：

  10.1021/np900440d
• 作为产物：
  描述：

  (3-ethoxycarbonyloxy-4-methoxy-phenyl)-acetic acid 在 磷酸酐 、 五氯化磷 、 甲苯 、 苯 作用下， 生成 1-(3-ethoxycarbonyloxy-4-methoxy-benzyl)-6,7-dimethoxy-3,4-dihydro-isoquinoline
  参考文献：
  名称：

  Spaeth; Lang, Monatshefte fur Chemie, 1921, vol. 42, p. 278

  摘要：

  DOI：