2,5-dioxopyrrolidin-1-yl 3,4-dimethylbenzoate | 541527-97-3

• 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: 2,5-dioxopyrrolidin-1-yl 3,4-dimethylbenzoate
• 英文别名: 2,5-Pyrrolidinedione, 1-[(3,4-dimethylbenzoyl)oxy]-；(2,5-dioxopyrrolidin-1-yl) 3,4-dimethylbenzoate
• CAS: 541527-97-3
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: DQJZLDPKLKHTIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 一氧化碳 、 4-溴-1,2-二甲苯 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90%的产率得到2,5-dioxopyrrolidin-1-yl 3,4-dimethylbenzoate
  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

• Preparation of N-hydroxysuccinimido esters via palladium-catalyzed carbonylation of aryl triflates and halides
  作者：Rongliang Lou、Melissa VanAlstine、Xufeng Sun、Mark P. Wentland

  DOI：10.1016/s0040-4039(03)00337-x

  日期：2003.3

  N-Hydroxysuccinimido esters of aromatic carboxylic acids (a.k.a. active esters) can be made using a potentially general, one-step procedure via Pd-catalyzed carbonylation of an aryl triflate or aryl iodide with CO and N-hydroxysuccinimide. Excellent yields (up to 94%) were observed when the reaction was done in DMSO at 70degreesC and 1 atmosphere of CO pressure. (C) 2003 Elsevier Science Ltd. All rights reserved.
• 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.