18-Acetyl-19-triethylsilyl-11-oxa-18-azatricyclo[12.5.2.017,20]henicosa-1(19),14(21),15,17(20)-tetraen-10-one | 1420009-22-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 18-Acetyl-19-triethylsilyl-11-oxa-18-azatricyclo[12.5.2.017,20]henicosa-1(19),14(21),15,17(20)-tetraen-10-one
• 英文别名: 18-acetyl-19-triethylsilyl-11-oxa-18-azatricyclo[12.5.2.017,20]henicosa-1(19),14(21),15,17(20)-tetraen-10-one
• CAS: 1420009-22-8
• 化学式: C₂₇H₄₁NO₃Si
• 分子量: 455.713
• InChiKey: DVJZORVEAGIDPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氨基苯乙醇 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 1,1'-bis(di-tertbutylphosphino)ferrocene 、 四丁基氟化铵 、 palladium diacetate 、 叔丁基二甲基氯硅烷 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 18-Acetyl-19-triethylsilyl-11-oxa-18-azatricyclo[12.5.2.017,20]henicosa-1(19),14(21),15,17(20)-tetraen-10-one
  参考文献：
  名称：

  A Pd(0)-Mediated Indole (Macro)cyclization Reaction

  摘要：

  Herein we report a systematic study of the Larock indole annulation designed to explore the scope and define the generality of its use in macrocyclization reactions, its use in directly accessing the chloropeptin I versus II DEF ring system as well as key unnatural isomers, its utility for both peptide-derived and more conventional carbon-chain based macrocycles, and its extension to intramolecular cyclizations with formation of common ring sizes. The studies define a powerful method complementary to the Stile or Suzuki cross-coupling reactions for the synthesis of cyclic or macrocyclic ring systems containing an embedded indole, tolerating numerous functional groups and incorporating various (up to 28-membered) ring sizes. As a result of the efforts to expand the usefulness and scope of the reaction, we also disclose a catalytic variant of the reaction, along with a powerful Pd-2(dba)(3)-derived catalyst system, and an examination of the factors impacting reactivity and catalysis.

  DOI：

  10.1021/ja3121394

文献信息

• A Pd(0)-Mediated Indole (Macro)cyclization Reaction
  作者：Steven P. Breazzano、Yam B. Poudel、Dale L. Boger

  DOI：10.1021/ja3121394

  日期：2013.1.30

  Herein we report a systematic study of the Larock indole annulation designed to explore the scope and define the generality of its use in macrocyclization reactions, its use in directly accessing the chloropeptin I versus II DEF ring system as well as key unnatural isomers, its utility for both peptide-derived and more conventional carbon-chain based macrocycles, and its extension to intramolecular cyclizations with formation of common ring sizes. The studies define a powerful method complementary to the Stile or Suzuki cross-coupling reactions for the synthesis of cyclic or macrocyclic ring systems containing an embedded indole, tolerating numerous functional groups and incorporating various (up to 28-membered) ring sizes. As a result of the efforts to expand the usefulness and scope of the reaction, we also disclose a catalytic variant of the reaction, along with a powerful Pd-2(dba)(3)-derived catalyst system, and an examination of the factors impacting reactivity and catalysis.