(12aS)-1-benzyl-9t-methyl-(12ar,13ac)-1,2,3,12a,13,13a-hexahydro-9H-10-oxa-1,7b-diaza-benzo[5,6]cyclohepta[1,2,3-jk]fluorene-12-carboxylic acid methyl ester | 55855-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (12aS)-1-benzyl-9t-methyl-(12ar,13ac)-1,2,3,12a,13,13a-hexahydro-9H-10-oxa-1,7b-diaza-benzo[5,6]cyclohepta[1,2,3-jk]fluorene-12-carboxylic acid methyl ester
• 英文别名: ent-4-benzyl-21β-methyl-(15α)-adifola-16,19-diene-16-carboxylic acid methyl ester
• CAS: 55855-68-0
• 化学式: C₂₈H₂₈N₂O₃
• 分子量: 440.542
• InChiKey: JFPRAOFSYICLKV-QGUBCYKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  43.7
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  苄基-[2-(1H-吲哚-3-基)-乙基]-胺 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (12aS)-1-benzyl-9t-methyl-(12ar,13ac)-1,2,3,12a,13,13a-hexahydro-9H-10-oxa-1,7b-diaza-benzo[5,6]cyclohepta[1,2,3-jk]fluorene-12-carboxylic acid methyl ester
  参考文献：
  名称：

  Chemistry of secologanin. Part 5. Graphical analysis of the acidic deglycosylation of vincoside derivatives

  摘要：

  Acidic hydrolysis and cyclization were studied in vincoside glycosides ('natural' series) and their dihydro derivatives ('dihydro' series) in which either one or both N atoms were free or blocked by an alkyl group. For interpretation of the results, a graph was constructed in which 25 points (actually circles) represent a maximum of 81 aglycone types and 40 arrows indicate 131 possible cyclizations. The reaction matrix of the graph was under thermodynamic control and in most cases afforded the thermodynamically most stable product aglycones. In addition to the deglycosylation, two types of cyclization were observed. In azacyclizations, the preferred nucleophilic site is N-4 over N-1, and the preferred electrophilic site is C-22 in the glycosides, C-21 over C-19 and C-17 in aglycones. In oxacyclizations, the preferred nucleophilic site is O-17 over C-18 and C-21, and the preferred electrophilic site is C-19 over C-21 and C-17 in the 'natural' series, C-21 over C-17 in the 'dihydro' series. In one case, the kinetically favoured aglycone types which had been generated in the reaction mixture were trapped in a subsequent reaction (outside the graph) before thermodynamic equilibrium was attained. With the help of graphical analysis it was possible to justify the formation of the most favourable and actually isolated products and pathways out of a large number of possibilities. (C) 1998 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199808/09)11:8/9<622::aid-poc51>3.0.co;2-l

文献信息

• Biomimetic conversion of vincoside into heteroyohimbine alkaloids
  作者：Richard T. Brown、C. Lyn Chapple

  DOI：10.1039/c39740000740

  日期：——

  The indole alkaloids 19-epiajmalicine (11), 3-iso-19-epiajmalicine(10), and their oxindole derivatives, formosanine (13) and isoformosanine (14) have been synthesised from a vincoside derivative in a biogenetically patterned reaction sequence.

  吲哚生物碱19-表艾玛西林（11），3-iso-19-表艾玛西林（10）以及它们的羟吲哚衍生物，甲酸鸟嘌呤（13）和异甲鸟嘌呤（14）已从一种长春菊苷衍生物以生物遗传学模式化的反应顺序合成。