trans-10,11-dimethoxy-5,6,7,8-tetrahydrodibenzo[c,g]azecin-5-one | 213825-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: trans-10,11-dimethoxy-5,6,7,8-tetrahydrodibenzo[c,g]azecin-5-one
• 英文别名: (13E)-10,11-dimethoxy-7,8-dihydro-6H-benzo[e][2]benzazecin-5-one
• CAS: 213825-76-4
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: RUMOZAKVJAUBLJ-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-10,11-dimethoxy-5,6,7,8-tetrahydrodibenzo[c,g]azecin-5-one 在 二甲基二环氧乙烷 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以78%的产率得到trans-13-hydroxy-2,3-dimethoxy-8-oxotetrahydroprotoberberine
  参考文献：
  名称：

  Dioxirane Epoxidation of 10-Membered-Ring Stilbene Lactams as Synthetic Precursors to Protoberberines

  摘要：

  Silylated stilbene lactams 1, prepared by intramolecular addition of an aryl radical to a trimethylsilylacetylene, were converted into protoberberines by dimethyldioxirane (DMD) epoxidation and subsequent acid-catalyzed cyclization of the epoxysilane with HCl. Treatment of the nonsilylated trans- and cis-stilbene derivatives with DMD afforded 13-hydroxytetrahydroprotoberberines and 13a-hydroxy-13-ketotetrahydroprotoberberines as the main products. Tetrahydroprotoberberines were also obtained in excellent yields by the reaction of both silylated and nonsilylated lactams with hydriodic acid.

  DOI：

  10.1021/jo981829n
• 作为产物：
  描述：

  N-[2-(2-bromo-4,5-dimethoxyphenyl)ethyl]-2-iodobenzamide 在 copper(l) iodide 、 偶氮二异丁腈 、 (Ph₃P)PdCl₂ 、 三正丁基氢锡 、 potassium carbonate 作用下， 以 甲醇 、 三乙胺 、 苯 为溶剂， 生成 trans-10,11-dimethoxy-5,6,7,8-tetrahydrodibenzo[c,g]azecin-5-one
  参考文献：
  名称：

  Transannular cyclizations of 10-membered lactams: An easy route to isoquinoline alkaloids

  摘要：

  Transannular cyclization of 10-membered ring lactams with hydriodic acid or fluoride gave tetrahydroprotoberberines or isoindolobenzazepines, respectively. The starting macrolactams were prepared by intramolecular addition of an aryl radical to a trimethylsilylacetylene. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01363-x

文献信息

• Transannular cyclizations of 10-membered lactams: An easy route to isoquinoline alkaloids
  作者：Gema Rodríguez、Luis Castedo、Domingo Domínguez、Carlos Saá

  DOI：10.1016/s0040-4039(98)01363-x

  日期：1998.9

  Transannular cyclization of 10-membered ring lactams with hydriodic acid or fluoride gave tetrahydroprotoberberines or isoindolobenzazepines, respectively. The starting macrolactams were prepared by intramolecular addition of an aryl radical to a trimethylsilylacetylene. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Dioxirane Epoxidation of 10-Membered-Ring Stilbene Lactams as Synthetic Precursors to Protoberberines
  作者：Gema Rodríguez、Luis Castedo、Domingo Domínguez、Carlos Saá、Waldemar Adam、Chantu R. Saha-Möller

  DOI：10.1021/jo981829n

  日期：1999.2.1

  Silylated stilbene lactams 1, prepared by intramolecular addition of an aryl radical to a trimethylsilylacetylene, were converted into protoberberines by dimethyldioxirane (DMD) epoxidation and subsequent acid-catalyzed cyclization of the epoxysilane with HCl. Treatment of the nonsilylated trans- and cis-stilbene derivatives with DMD afforded 13-hydroxytetrahydroprotoberberines and 13a-hydroxy-13-ketotetrahydroprotoberberines as the main products. Tetrahydroprotoberberines were also obtained in excellent yields by the reaction of both silylated and nonsilylated lactams with hydriodic acid.