2-benzyl-3-(4-methoxyphenyl)isoindolin-1-one | 1311147-15-5

• 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-benzyl-3-(4-methoxyphenyl)isoindolin-1-one
• 英文别名: 2-benzyl-3-(4-methoxyphenyl)-3H-isoindol-1-one
• CAS: 1311147-15-5
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: DHFOVRYVBLBBBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-benzyl-N-(2-(tert-butylamino)-1-(4-methoxyphenyl)-2-oxoethyl)-2-iodobenzamide 在 copper(l) iodide 、 1,10-菲罗啉 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 以72%的产率得到2-benzyl-3-(4-methoxyphenyl)isoindolin-1-one
  参考文献：
  名称：

  Facile synthesis of diverse isoindolinone derivatives via Ugi-4CR followed by Cu-catalyzed deamidative C(sp2)–C(sp3) coupling

  摘要：

  The present work highlights a synthetic approach to the diverse isoindolinone derivatives using Ugi-4CR followed by a Cu-catalyzed deamidative C-C coupling reaction.This two-step sequence tolerates a broad range of amines, aldehydes, and isocyanides as starting materials for Ugi-4CR products to provide medicinally relevant isoindolinone derivatives in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.091

文献信息

• Copper-Catalyzed C(sp³)–OH Cleavage with Concomitant C–C Coupling: Synthesis of 3-Substituted Isoindolinones
  作者：H. Surya Prakash Rao、A. Veera Bhadra Rao

  DOI：10.1021/jo502446k

  日期：2015.2.6

  Copper(II) trifluoromethanesulfonate (Cu(OTf)2) efficiently catalyzes the C–C coupling of 3-hydoxyisoindolinones with a variety of aryl-, heteroaryl-, and alkenylboronic acids to furnish C(3) aryl-, heteroaryl-, and alkenyl-substituted isoindolinones. The coupling reactions work smoothly in 1,2-dicholoroethane (DCE) reflux, to effect both inter- and intramolecular versions. This is the first report

  三氟甲磺酸铜（II）（Cu（OTf）2）有效催化3-羟基异吲哚满酮与各种芳基，杂芳基和烯基硼酸的CC偶联，提供C（3）芳基，杂芳基和烯基取代的异吲哚啉酮。偶联反应在1,2-二氯乙烷（DCE）回流中能顺利进行，从而影响分子间和分子内两种形式。这是有关C（sp 3）-OH裂解并伴随C-C偶联的第一个报告。光不稳定的2-硝基苄基保护基最适合于促进偶联反应和脱保护。生物碱神经胺的四环基序是通过应用新开发的铜催化的CC偶联制备的。
• Tandem C( <i>sp</i> ³ )−H Arylation/Oxidation and Arylation/Allylic Substitution of Isoindolinones
  作者：Jacqueline Jiménez、Byeong‐Seon Kim、Patrick J. Walsh

  DOI：10.1002/adsc.201600654

  日期：2016.9

  derivatives, which exhibit anti‐tumor activity, can be accessed via a tandem reaction. Thus, when the arylation product is exposed to air under basic conditions, in situ oxidation takes place to install the 3‐hydroxy group. Furthermore, a tandem arylation/allylic substitution reaction is advanced in which both the arylation and allylic substitution are catalyzed by the same palladium catalyst. Finally

  异吲哚酮包含一类重要的药用活性化合物。在此，我们报告了使用乙酸钯 (II)/NIXANTPHOS 基催化剂系统对异吲哚啉酮与芳基溴化物进行直接官能化（22 个示例）。此外，还可以通过串联反应获得具有抗肿瘤活性的 3-芳基-3-羟基异二氢吲哚酮衍生物。因此，当芳基化产物在碱性条件下暴露于空气时，会发生原位氧化以安装3-羟基。此外，进行串联芳基化/烯丙基取代反应，其中芳基化和烯丙基取代均由相同的钯催化剂催化。最后，提出了串联芳基化/烷基化程序。这些串联反应使得能够从常见的起始材料合成各种结构不同的异吲哚酮衍生物。
• Nickel(0)-Catalyzed Cyclization of <i>N</i>-Benzoylaminals for Isoindolinone Synthesis
  作者：Danielle M. Shacklady-McAtee、Srimoyee Dasgupta、Mary P. Watson

  DOI：10.1021/ol201248c

  日期：2011.7.1

  A nickel(0) catalyst effectively mediates the cyclization of N-benzoyl aminals in the presence of a stoichiometric Lewis acid. This method enables preparation of a variety of isoindolinones with substitution on the benzoyl fragment and C-3 carbon. This reaction likely proceeds via an α-amidoalkylnickel(II) intermediate, which then may cyclize via either an electrophilic aromatic substitution or an

  在化学计量的路易斯酸存在下，镍（0）催化剂可有效介导N-苯甲酰缩醛的环化反应。该方法使得能够制备在苯甲酰基片段和C-3碳上具有取代基的各种异吲哚啉酮。该反应可能通过α-酰胺基烷基镍（II）中间体进行，然后可以通过亲电芳族取代或插入途径进行环化。
• <i>N</i>-Capping of Primary Amines with 2-Acyl-benzaldehydes To Give Isoindolinones
  作者：Daniel Augner、Dario C. Gerbino、Nikolay Slavov、Jörg-Martin Neudörfl、Hans-Günther Schmalz

  DOI：10.1021/ol202271k

  日期：2011.10.7

  A unique reactivity pattern, first observed in the conversion of the marine natural product pestalone into pestalachloride A, was investigated. It was shown that 2-formyl-arylketones smoothly react with ammonia and primary amines, respectively, under mild conditions to afford 3-substituted isoindolinones in high yield. The reaction represents a new option for the derivatization (N-capping) of primary amines. As the substrates are readily accessible the methodology opens a short and modular access to pharmaceutically relevant substituted isoindolinones.