13a-trimethylsilyl-10,11-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquino[3,2-a]isoquinolin-8-one | 213825-79-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: 13a-trimethylsilyl-10,11-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquino[3,2-a]isoquinolin-8-one
• 英文别名: 10,11-dimethoxy-13a-trimethylsilyl-6,13-dihydro-5H-isoquinolino[2,1-b]isoquinolin-8-one
• CAS: 213825-79-7
• 化学式: C₂₂H₂₇NO₃Si
• 分子量: 381.547
• InChiKey: LVAZNGDLFDTBHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  13a-trimethylsilyl-10,11-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquino[3,2-a]isoquinolin-8-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以76%的产率得到10,11-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquino[3,2-a]isoquinolin-8-one
  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：

  邻溴苯乙胺 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 偶氮二异丁腈 、 氢碘酸 、 碘 、 三正丁基氢锡 、 silver trifluoroacetate 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 三乙胺 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 38.5h， 生成 13a-trimethylsilyl-10,11-dimethoxy-6,8,13,13a-tetrahydro-5H-isoquino[3,2-a]isoquinolin-8-one
  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

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.