N-(2,6-difluorophenyl)phthalimide | 120371-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(2,6-difluorophenyl)phthalimide
• 英文别名: 1H-Isoindole-1,3(2H)-dione, 2-(2,6-difluorophenyl)-；2-(2,6-difluorophenyl)isoindole-1,3-dione
• CAS: 120371-26-8
• 化学式: C₁₄H₇F₂NO₂
• 分子量: 259.212
• InChiKey: MHWHIYXERPBBRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethylzinc 、 N-(2,6-difluorophenyl)phthalimide 在 2,2'-联吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 作用下， 以 二甲基亚砜 为溶剂， 以61%的产率得到N-(2,6-difluorophenyl)-2-ethylbenzamide
  参考文献：
  名称：

  Decarbonylative cross coupling of phthalimides with diorganozinc reagents—Efforts toward catalysis

  摘要：

  The decarbonylative coupling of phthalimides with diorganozinc reagents to form o-substituted benzamides has been previously demonstrated as a viable process, but only with stoichiometric nickel(0). Investigations into a number of reaction variables, including solvent, ligand, and substrate substitution, have yielded multiple sets of conditions capable of achieving up to 10 catalyst turnovers, most successfully with the use of electron withdrawing nitrogen substituents on the phthalimide. In addition, these investigations have provided insight into the intermediates within the catalytic cycle and have revealed new approaches to the development of a general catalytic methodology. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.02.017
• 作为产物：
  描述：

  2-氰基苯甲酸甲酯 、 bis(2,6-difluorophenyl)iodine(III) trifluoromethanesulfonate 在 copper(I) bromide 作用下， 以 1,2-二氯乙烷 为溶剂， 以76 %的产率得到N-(2,6-difluorophenyl)phthalimide
  参考文献：
  名称：

  氰基酯与二芳基碘盐的串联 N-芳基化-酰化和重排反应高效合成环状酰亚胺

  摘要：

  可在线获取 用氰基酯和二芳基碘盐开发了一种合成多取代环状酰亚胺的有效方法。该方法通过级联的N-芳基化-酰化和重排进行，以良好的收率（高达 99%）提供目标杂环。该方法的主要优点是底物适用范围广，官能团相容性好。该策略还扩展到稠合环状酰亚胺，如丙二酰亚胺、琥珀酰亚胺和戊二酰亚胺。

  DOI：

  10.1016/j.cclet.2022.107913

文献信息

• US4766243A
  申请人：——

  公开号：US4766243A

  公开（公告）日：1988-08-23
• Decarbonylative cross coupling of phthalimides with diorganozinc reagents—Efforts toward catalysis
  作者：Kimberly S. DeGlopper、Sarah K. Fodor、Thomas B.D. Endean、Jeffrey B. Johnson

  DOI：10.1016/j.poly.2016.02.017

  日期：2016.8

  The decarbonylative coupling of phthalimides with diorganozinc reagents to form o-substituted benzamides has been previously demonstrated as a viable process, but only with stoichiometric nickel(0). Investigations into a number of reaction variables, including solvent, ligand, and substrate substitution, have yielded multiple sets of conditions capable of achieving up to 10 catalyst turnovers, most successfully with the use of electron withdrawing nitrogen substituents on the phthalimide. In addition, these investigations have provided insight into the intermediates within the catalytic cycle and have revealed new approaches to the development of a general catalytic methodology. (C) 2016 Elsevier Ltd. All rights reserved.
• Efficient synthesis of cyclic imides by the tandem N-arylation-acylation and rearrangement reaction of cyanoesters with diaryliodonium salts
  作者：Zhiyuan Bao、Chao Chen

  DOI：10.1016/j.cclet.2022.107913

  日期：2023.5

  multi-substituted cyclic imides was developed with cyanoesters and diaryliodonium salts. This method proceeds through a cascade of N-arylation-acylation and rearrangement to give target heterocycles in good yields (up to 99%). This method has the major advantages of a broad substrate scope, excellent functional group compatibility. The strategy was also extended to the fused cyclic imides, such as malonimides

  可在线获取 用氰基酯和二芳基碘盐开发了一种合成多取代环状酰亚胺的有效方法。该方法通过级联的N-芳基化-酰化和重排进行，以良好的收率（高达 99%）提供目标杂环。该方法的主要优点是底物适用范围广，官能团相容性好。该策略还扩展到稠合环状酰亚胺，如丙二酰亚胺、琥珀酰亚胺和戊二酰亚胺。