butyl (N-phenyl-isoindolin-1-on-3-yl)acetate | 871570-96-6

• 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: butyl (N-phenyl-isoindolin-1-on-3-yl)acetate
• 英文别名: n-butyl 2-(3-oxo-2-phenylisoindolin-1-yl)acetate；butyl 2-(3-oxo-2-phenylisoindolin-1-yl)acetate；butyl 2-(3-oxo-2-phenyl-1H-isoindol-1-yl)acetate
• CAS: 871570-96-6
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: DNVODQPEELASCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  butyl (N-phenyl-isoindolin-1-on-3-yl)acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以54%的产率得到N-phenyl-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 butyl (N-phenyl-isoindolin-1-on-3-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

• Ruthenium-catalyzed Oxidative Alkenylation of Arenes via Regioselective C–H Bond Cleavage Directed by a Nitrogen-containing Group
  作者：Yuto Hashimoto、Takumi Ueyama、Tatsuya Fukutani、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1246/cl.2011.1165

  日期：2011.10.5

  Direct alkenylation of 1-phenylpyrazoles with alkenes such as acrylates accompanied by regioselective C–H bond cleavage proceeds efficiently under ruthenium catalysis in the presence of a copper oxidant. The procedure is also applicable to 2-phenylbenzothiazole and benzanilide.

  在铜氧化剂存在下，1-苯基吡唑与烯（如丙烯酸酯）的直接烯化反应伴随着区域选择性 C-H 键裂解在钌催化下高效进行。该过程也适用于 2-苯基苯并噻唑和苯并苯胺。
• Carbene-Catalyzed Tandem Imine Umpolung–Intramolecular Aza-Conjugate Addition–Oxidation to Access <i>N</i>-Substituted Isoindolinones
  作者：Jakkula Ramarao、Purna Chandra Behera、Manyam Subbi Reddy、Surisetti Suresh

  DOI：10.1021/acs.joc.3c02187

  日期：2024.1.5

  proceeds through NHC-catalyzed tandem imine umpolung–intramolecular aza-Michael addition followed by oxidation, while molecular oxygen in air acts as a sole oxidant. Atom efficiency, operational simplicity, large-scale syntheses, and mild reaction conditions are the salient features of this method. Mechanistic studies were indicative of the necessity of molecular oxygen in air as oxidant for the conversion

  在此，我们描述了一种新型的 N-杂环卡宾 (NHC) 催化合成N-取代异吲哚酮乙酸酯。所提出的转化通过 NHC 催化的串联亚胺 umpolung-分子内氮杂迈克尔加成进行，然后进行氧化，而空气中的分子氧充当唯一的氧化剂。原子效率、操作简单、大规模合成和反应条件温和是该方法的显着特点。机理研究表明空气中的分子氧作为亚胺转化为酰胺的氧化剂的必要性。
• Palladium mediated synthesis of isoindolinones and isoquinolinones
  作者：Md. Wahab Khan、A.F.G. Masud Reza

  DOI：10.1016/j.tet.2005.09.032

  日期：2005.11

  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.