N-[2-(2-bromophenyl)ethyl]-4,5-dimethoxy-2-[(trimethylsilyl)ethynyl]benzamide | 213825-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-(2-bromophenyl)ethyl]-4,5-dimethoxy-2-[(trimethylsilyl)ethynyl]benzamide
• 英文别名: N-[2-(2-bromophenyl)ethyl]-4,5-dimethoxy-2-(2-trimethylsilylethynyl)benzamide
• CAS: 213825-64-0
• 化学式: C₂₂H₂₆BrNO₃Si
• 分子量: 460.443
• InChiKey: MACPRWGWRVOKJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  N-[2-(2-bromophenyl)ethyl]-4,5-dimethoxy-2-[(trimethylsilyl)ethynyl]benzamide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以70%的产率得到2,3-dimethoxy-13-trimethylsilyl-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
• 作为产物：
  描述：

  邻溴苯乙胺 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 碘 、 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 为溶剂， 反应 26.5h， 生成 N-[2-(2-bromophenyl)ethyl]-4,5-dimethoxy-2-[(trimethylsilyl)ethynyl]benzamide
  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.