| 1420010-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1420010-31-6
• 化学式: C₂₈H₃₃BrN₂O₅
• 分子量: 557.484
• InChiKey: HIRQUDJTTWPQBB-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  92.04
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 、 4-二甲氨基吡啶 、 N-羟基-7-氮杂苯并三氮唑 、 1,1'-bis(di-tertbutylphosphino)ferrocene 、 palladium diacetate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 17.0h， 生成 tert-butyl N-[(12R,15R,18R)-8-acetyl-15-(3,5-dichloro-4-methoxyphenyl)-21,22-dimethoxy-13,16-dioxo-18-(phenylmethoxymethyl)-9-triethylsilyl-8,14,17-triazatetracyclo[17.3.1.02,7.06,10]tricosa-1(22),2,4,6,9,19(23),20-heptaen-12-yl]carbamate
  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
• 作为产物：
  描述：

  (R)-tert-butyl 2-(benzyloxy)-1-(3-iodo-4,5-dimethoxyphenyl)ethylcarbamate 在 盐酸 、 四(三苯基膦)钯 、 异丙基氯化镁 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 44.0h， 生成
  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