2,5-dioxopyrrolidin-1-ylisoquinoline-4-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2,5-dioxopyrrolidin-1-ylisoquinoline-4-carboxylate
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) isoquinoline-4-carboxylate；(2,5-dioxopyrrolidin-1-yl) isoquinoline-4-carboxylate
• 化学式: C₁₄H₁₀N₂O₄
• 分子量: 270.244
• InChiKey: IFXZYPUKOVGZNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 4-溴异喹啉 、 一氧化碳 在 N-甲基二环己基胺 、 [{Pd(cinnamyl)Cl}2] 、 9-methyl-9H-fluorene-9-carbonyl chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 16.0h， 以91%的产率得到2,5-dioxopyrrolidin-1-ylisoquinoline-4-carboxylate
  参考文献：
  名称：

  General Method for the Preparation of Active Esters by Palladium-Catalyzed Alkoxycarbonylation of Aryl Bromides

  摘要：

  A useful method was developed for the synthesis of active esters by palladium-catalyzed alkoxycarbonylation of (hetero)aromatic bromides. The protocol was general for a range of oxygen nucleophiles including N-hydroxysuccinimide (NHS), pentafluorophenol (PFP), hexafluoroisopropyl alcohol (HFP), 4-nitrophenol, and N-hydroxyphthalimide. A high functional group tolerance was displayed, and several active esters were prepared with good to excellent isolated yields. The protocol was extended to access an important synthetic precursor to the HIV-protease inhibitor, saquinavir, by formation of an NHS ester followed by acyl substitution.

  DOI：

  10.1021/jo5025464

文献信息

• General Method for the Preparation of Active Esters by Palladium-Catalyzed Alkoxycarbonylation of Aryl Bromides
  作者：Angelina M. de Almeida、Thomas L. Andersen、Anders T. Lindhardt、Mauro V. de Almeida、Troels Skrydstrup

  DOI：10.1021/jo5025464

  日期：2015.2.6

  A useful method was developed for the synthesis of active esters by palladium-catalyzed alkoxycarbonylation of (hetero)aromatic bromides. The protocol was general for a range of oxygen nucleophiles including N-hydroxysuccinimide (NHS), pentafluorophenol (PFP), hexafluoroisopropyl alcohol (HFP), 4-nitrophenol, and N-hydroxyphthalimide. A high functional group tolerance was displayed, and several active esters were prepared with good to excellent isolated yields. The protocol was extended to access an important synthetic precursor to the HIV-protease inhibitor, saquinavir, by formation of an NHS ester followed by acyl substitution.