2-(2,3-dichlorophenyl)-1H-isoindole-1,3(2H)-dione | 26180-00-7

• 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: 2-(2,3-dichlorophenyl)-1H-isoindole-1,3(2H)-dione
• 英文别名: N-(2,3-dichlorophenyl)phthalimide；N-(2,3-Dichlor-phenyl)-phthalimid；2-(2,3-dichlorophenyl)isoindoline-1,3-dione；2-(2,3-dichlorophenyl)isoindole-1,3-dione
• CAS: 26180-00-7
• 化学式: C₁₄H₇Cl₂NO₂
• 分子量: 292.121
• InChiKey: FDIGKGNICSGZBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  2

反应信息

• 作为产物：
  描述：

  苯酐 、 2,3-二氯苯胺 在 溶剂黄146 作用下， 生成 2-(2,3-dichlorophenyl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  氮为中心的自由基介导的芳烃和杂芳烃的CH酰亚胺通过可见光诱导的光催化作用。

  摘要：

  芳烃和杂芳烃的CH酰亚胺化是通过可见光诱导的光催化实现的。在铱（III）光氧化还原催化剂的存在下，芳族底物与N-氯邻苯二甲酰亚胺的反应在室温下通过以氮为中心的自由基介导的芳族取代提供N-芳基产物。

  DOI：

  10.1039/c4cc03905j

文献信息

• Metal-Free Intermolecular Oxidative C–N Bond Formation via Tandem C–H and N–H Bond Functionalization
  作者：Abhishek A. Kantak、Shathaverdhan Potavathri、Rose A. Barham、Kaitlyn M. Romano、Brenton DeBoef

  DOI：10.1021/ja2087085

  日期：2011.12.14

  development of a novel intermolecular oxidative amination reaction, a synthetic transformation that involves the simultaneous functionalization of both a N-H and C-H bond, is described. The process, which is mediated by an I(III) oxidant and contains no metal catalysts, provides a rapid and green method for synthesizing protected anilines from simple arenes and phthalimide. Mechanistic investigations

  描述了一种新型分子间氧化胺化反应的发展，这是一种合成转化，涉及同时对 NH 和 CH 键进行功能化。该过程由 I(III) 氧化剂介导，不含金属催化剂，为从简单的芳烃和邻苯二甲酰亚胺合成受保护的苯胺提供了一种快速、绿色的方法。机理研究表明，该反应是通过邻苯二甲酰亚胺对芳族自由基阳离子的亲核攻击进行的，这与已报道的其他 I(III) 胺化反应的亲电芳族胺化相反。证明了这种新反应在合成各种取代苯胺衍生物中的应用。
• Sterically Controlled, Palladium-Catalyzed Intermolecular Amination of Arenes
  作者：Ruja Shrestha、Paramita Mukherjee、Yichen Tan、Zachary C. Litman、John F. Hartwig

  DOI：10.1021/ja4032677

  日期：2013.6.12

  the Pd-catalyzed amination of arenes to form N-aryl phthalimides with regioselectivity controlled predominantly by steric effects. Mono-, di-, and trisubstituted arenes lacking a directing group undergo amination reactions with moderate to high yields and high regioselectivities from sequential addition of PhI(OAc)2 as an oxidant in the presence of Pd(OAc)2 as catalyst. This sterically derived selectivity

  我们报告了 Pd 催化的芳烃胺化形成 N-芳基邻苯二甲酰亚胺，其区域选择性主要受空间效应控制。在 Pd(OAc) 2 作为催化剂的存在下，连续加入作为氧化剂的 PhI(OAc) 2 后，缺乏导向基团的单、二和三取代的芳烃可以进行中等至高产率和高区域选择性的胺化反应。这种空间衍生的选择性与类似的芳烃乙酰氧基化形成对比。
• Regioselective Gold-Catalyzed Oxidative C–N Bond Formation
  作者：Louis Marchetti、Abhishek Kantak、Riley Davis、Brenton DeBoef

  DOI：10.1021/ol5034805

  日期：2015.1.16

  A novel protocol for the regioselective intermolecular amination of various arenes has been developed. By using an I(III) oxidant in the presence of a Au(I) catalyst, a direct and novel route for regioselectively accessing a variety of substituted aniline moieties has been achieved with yields as high as 90%. Mechanistic insight suggests that regioselectivity can be predicted based on electrophilic

  已经开发出用于各种芳烃的区域选择性分子间胺化的新方案。通过在Au（I）催化剂存在下使用I（III）氧化剂，已经实现了区域选择性地访问各种取代苯胺部分的直接和新颖途径，收率高达90％。机械学的见解表明，可以基于亲电子的芳族金属化模式来预测区域选择性。
• Intermolecular Oxidative C–N Bond Formation under Metal-Free Conditions: Control of Chemoselectivity between Aryl sp² and Benzylic sp³ C–H Bond Imidation
  作者：Hyun Jin Kim、Jiyu Kim、Seung Hwan Cho、Sukbok Chang

  DOI：10.1021/ja207296y

  日期：2011.10.19

  A new synthetic approach toward intermolecular oxidative C-N bond formation of arenes has been developed under transition-metal-free conditions. Complete control of chemoselectivity between aryl sp(2) and benzylic sp(3) C-H bond imidation was achieved by the choice of nitrogen sources, representatively being phthalimide and dibenzenesulfonimide, respectively.
• Towards the synthesis of amino[b,e][1,4]dioxin derivatives via cationic ruthenium complexes
  作者：Richard C. Cambie、George R. Clark、Sheryl L. Coombe、Sally A. Coulson、Peter S. Rutledge、Paul D. Woodgate

  DOI：10.1016/0022-328x(95)05717-4

  日期：1996.1

  Double nucleophilic aromatic substitution reactions between N-substituted (eta(6)-1,2-dichlorobenzene)RuCp(+) salts and substituted 1,2-benzenediols have been carried out under mild conditions to prepare N-substituted (eta(6)-dibenzo[b,e][1,4]dioxin)ruthenium(II) complexes. The dibenzodioxin ligands were subsequently liberated by photolysis, with radiation from a sunlamp or from a medium pressure Hg lamp (300 nm).