methyl 2-(2-(4-methoxyphenyl)-3-oxoisoindolin-1-yl)acetate | 88460-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 2-(2-(4-methoxyphenyl)-3-oxoisoindolin-1-yl)acetate
• 英文别名: methyl 2-[2-(4-methoxyphenyl)-3-oxo-1H-isoindol-1-yl]acetate
• CAS: 88460-63-3
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: ULHUNORZGPVDCG-UHFFFAOYSA-N

物化性质

• 熔点：
  97-99 °C
• 沸点：
  468.7±45.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-(4-methoxyphenyl)-3-oxoisoindolin-1-yl)acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以61%的产率得到N-p-methoxyphenyl-1,2,3,4-tetrahydro-1-oxoisoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Palladium mediated synthesis of isoindolinones and isoquinolinones

  摘要：

  The palladium-catalyzed reactions of 2-iodo-N-substituted benzamides 5-10 with acrylic esters 11-14 led to N-substituted-3-alkylisoindolinone esters 15-22 in good yields. The esters of isoindolinones 15-22 underwent hydrolysis reactions yielding the N-aryl-1,2,3,4-tetrahydro-1-oxoisoquinoline-3-carboxylic acid 26-31 in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.032
• 作为产物：
  描述：

  邻碘苯甲酰氯 在 bis(triphenylphosphine)palladium(II)-chloride 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 23.0h， 生成 methyl 2-(2-(4-methoxyphenyl)-3-oxoisoindolin-1-yl)acetate
  参考文献：
  名称：

  Palladium mediated synthesis of isoindolinones and isoquinolinones

  摘要：

  The palladium-catalyzed reactions of 2-iodo-N-substituted benzamides 5-10 with acrylic esters 11-14 led to N-substituted-3-alkylisoindolinone esters 15-22 in good yields. The esters of isoindolinones 15-22 underwent hydrolysis reactions yielding the N-aryl-1,2,3,4-tetrahydro-1-oxoisoquinoline-3-carboxylic acid 26-31 in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.032

文献信息

• Ru(II)-Catalyzed Oxidative Olefination of Benzamides: Switchable Aza-Michael and Aza-Wacker Reaction for Synthesis of Isoindolinones
  作者：Manoj Kumar、Shalini Verma、Akhilesh K. Verma

  DOI：10.1021/acs.orglett.0c01237

  日期：2020.6.19

  Selective tandem oxidative C–H olefination–aza-Michael/aza-Wacker reaction of N-arylbenzamides is achieved by fine-tuning between base and additive to access valuable 3-oxoisoindolinyls and 3-oxoisoindolinylidenes, respectively. Careful optimization and control experiments provides a guiding principle in the design of a proposed catalytic cycle. The copper–iminium complex acting as a precursor for

  N-芳基苯甲酰胺的选择性串联氧化C–H烯化反应– aza-Michael / aza-Wacker反应是通过在碱和添加剂之间进行微调来分别获得有价值的3-氧代异吲哚基和3-氧代异吲哚基。仔细的优化和控制实验为拟议的催化循环的设计提供了指导原则。铜-亚胺络合物作为Ru催化剂的结合前体被分离出来，并通过X射线衍射证实。该催化系统的多功能性已通过生物相关分子的合成得到证明。
• Unified Approach to Isoindolinones and THIQs via Lewis Acid Catalyzed Domino Mukaiyama–Mannich Lactamization/Alkylations: Application in the Synthesis of (±)-Homolaudanosine
  作者：Sivasankaran Dhanasekaran、Anirban Kayet、Arun Suneja、Vishnumaya Bisai、Vinod K. Singh

  DOI：10.1021/acs.orglett.5b01197

  日期：2015.6.5

  variety of isoindolinones and tetrahydroisoquinolines via a Lewis acid catalyzed domino Mukaiyama–Mannich lactamization/alkylation is achieved. This transformation comprises a sequential formation of three new bonds through a one-pot, three-component procedure to afford product in moderate to high yields. A concise synthesis of (±)-homolaudanosine (2b) has been achieved using this method.

  通过路易斯酸催化的多米诺山Mukaiyama–Mannich内酰胺化/烷基化反应，可以实现新颖而有效的多种异吲哚啉酮和四氢异喹啉的合成。这种转变包括通过一锅三组分程序依次形成三个新的键，以提供中等至高收率的产物。使用此方法已实现了（±）-高麦芽糖苷（2b）的简明合成。
• Synthesis of 3-substituted isoindolin-1-ones via a palladium-catalysed 3-component carbonylation/amination/Michael addition process
  作者：Xinjie Gai、Ronald Grigg、Tossapol Khamnaen、Shuleewan Rajviroongit、Visuvanathar Sridharan、Lixin Zhang、Simon Collard、Ann Keep

  DOI：10.1016/j.tetlet.2003.08.036

  日期：2003.9

  A novel palladium-catalysed three component cascade process is described involving carbonylation of an aryl iodide to generate an acyl palladium species which is intercepted by a primary aliphatic/aromatic amine, amide or sulfonamide followed by intramolecular Michael addition to afford 3-substituted isoindolin-1-ones in good yield.

  描述了一种新颖的钯催化的三组分级联过程，涉及芳基碘化物的羰基化以生成酰基钯物质，该酰基钯物质被脂族/芳族伯胺，酰胺或磺酰胺所拦截，然后通过分子内迈克尔加成反应得到3-取代的异吲哚啉-1 -产量高。
• Synthesis of <i>N</i>-substituted isoindolinones via a palladium catalysed three-component carbonylation – amination – Michael addition cascade
  作者：Ronald Grigg、Xinjie Gai、Tossapol Khamnaen、Shuleewan Rajviroongit、Visuvanathar Sridharan、Lixin Zhang、Simon Collard、Ann Keep

  DOI：10.1139/v05-111

  日期：2005.6.1

  We herein describe a novel palladium catalysed three-component cascade process involving carbonylation of an aryl iodide to generate an acyl palladium(II) species that is intercepted by a primary aliphatic or aromatic amine, amide, or sulfonamide followed by intramolecular Michael addition to furnish N-substituted isoindolinones in good yield. Overall, the cascade results in the formation of one C—C and two C—N bonds, one ring and one stereocentre.Key words: isoindolinone, palladium, cascade, amidation, sulfonamidation.

  我们在此描述了一种新颖的钯催化的三组分级联过程，涉及芳基碘化物的羰基化生成酰基钯（II）物种，该物种被一级脂肪或芳香胺、酰胺或磺胺基拦截，随后进行分子内Michael加成，产生N-取代的异吲哚酮，收率良好。总体而言，级联反应导致形成一个C—C键和两个C—N键，一个环和一个立体中心。关键词：异吲哚酮，钯，级联，酰胺化，磺胺基化。
• Divergent Reactivity of 1,2,3-Benzotriazin-4(3<i>H</i>)-ones: Photocatalytic Synthesis of 3-Substituted Isoindolinones Achieved through a Nitrogen-Mediated Hydrogen Atom Shift
  作者：Fostino R. B. Bokosi、Oisin J. Shiels、Christopher Richardson、Adam J. Trevitt、Sinead T. Keaveney

  DOI：10.1021/acs.joc.3c02545

  日期：2024.2.2

  regioselective visible-light-mediated denitrogenative alkene insertion of 1,2,3-benzotriazin-4(3H)-ones was developed to access 3-substituted isoindolinones, an important structural motif present in many biologically active molecules and natural products. Notably, divergent reactivity was achieved by switching from reported nickel catalysis (where C3-substituted 3,4-dihydroisoquinolin-1(2H)-ones form) to

  开发了一种区域选择性可见光介导的 1,2,3-苯并三嗪-4(3 H )-酮的脱氮烯烃插入，以获取 3-取代异吲哚啉酮，这是许多生物活性分子和天然产物中存在的重要结构基序。值得注意的是，通过从报道的镍催化（其中形成 C3 取代的 3,4-二氢异喹啉-1(2 H )-酮）转向光催化，实现了不同的反应性，其中光催化脱氮和随后的氮介导的氢原子转移导致排他性3-取代异吲哚啉酮形成。所开发的光催化反应与活化的末端烯烃和环状α,β-不饱和酯和酮相容，对1,2,3-苯并三嗪-4(3 H )-酮的N-取代具有广泛的官能团耐受性。该过程的实用性通过克级合成和合成后酰胺化得以凸显。为了了解这种独特的产物选择性的起源，进行了实验和计算机制研究。