6-methoxyspiro[4H-2-benzazepine-5,4'-cyclohex-2-ene]-1,1',3-trione | 1194692-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 6-methoxyspiro[4H-2-benzazepine-5,4'-cyclohex-2-ene]-1,1',3-trione
• CAS: 1194692-23-3
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: SERVBXAYCMABQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methoxyspiro[4H-2-benzazepine-5,4'-cyclohex-2-ene]-1,1',3-trione 在 lithium aluminium tetrahydride 、 甲烷磺酸 、 2,4,6-三甲基吡啶对甲苯磺酸盐 、 potassium carbonate 、 DL-蛋氨酸 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 19.0h， 生成 11-methyl-7,8,9,10,11,12-hexahydro-4aH-[1]benzofuro[3a,3,2-ef][2]benzazepine-6(5H)-one
  参考文献：
  名称：

  Synthesis of Demethoxy-Lycoraminone

  摘要：

  Demethoxy-lycoraminone (8) was prepared in several steps starting from the appropriate benzo[c]azepine dione derivative (9). Ketone (9) was protected as a ketal group followed by methylation on the azepine nitrogen atom. After reduction of the imide carbonyl groups, deprotection, demethylation and ring closure were carried out as a one-pot reaction in methanesulfonic acid in the presence of racemic methionine.

  DOI：

  10.3987/com-10-12117

文献信息

• An unexpected rearrangement of the benzofurobenzazepine skeleton of galanthamine-type alkaloids
  作者：Klára Herke、László Hazai、Zsuzsanna Sánta、Zsófia Dubrovay、Viktor Háda、Csaba Szántay、György Kalaus、Csaba Szántay

  DOI：10.1016/j.tetlet.2010.10.158

  日期：2010.12

  Attempted cyclisation of N-methylated Spiro benzazepine-cyclohexenone (5) into the corresponding N-methyl tetracyclic unit of galanthamine-type alkaloids (6) instead gave an unexpected rearrangement to yield a cyclopentanoisoquinolinone derivative (7). Methylation of the tetrahydrobenzofurobenzazepine tetracycle resulted in the expected N-methyl derivative 6, and the anomalous product 8, with structure similar to that of 7. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of Demethoxy-Lycoraminone
  作者：Csaba Szántay、László Hazai、Zsófia Dubrovay、Viktor Háda、Zsuzsanna Sánta、Csaba Szántay、György Kalaus、Klára Herke

  DOI：10.3987/com-10-12117

  日期：——

  Demethoxy-lycoraminone (8) was prepared in several steps starting from the appropriate benzo[c]azepine dione derivative (9). Ketone (9) was protected as a ketal group followed by methylation on the azepine nitrogen atom. After reduction of the imide carbonyl groups, deprotection, demethylation and ring closure were carried out as a one-pot reaction in methanesulfonic acid in the presence of racemic methionine.