2-octylisoindolin-1-one | 532392-05-5

• 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-octylisoindolin-1-one
• 英文别名: 2-octyl-3H-isoindol-1-one
• CAS: 532392-05-5
• 化学式: C₁₆H₂₃NO
• 分子量: 245.365
• InChiKey: CDGHMDUGQDDPSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-octyl-2,3-dihydro-1H-isoindole 在 1,4-二氧六环 作用下， 反应 8.0h， 以69%的产率得到2-octylisoindolin-1-one
  参考文献：
  名称：

  异吲哚啉酮的合成：异吲哚啉的选择性二恶烷介导的好氧氧化

  摘要：

  N-烷基和N-芳基-异吲哚啉酮是通过二恶烷介导的异吲哚啉前体的氧化反应制备的。该转化表现出对异茚满碱独特的化学选择性。在氧化过程中手性叔（3°）-苄基位置未消旋，通过后期氧化制备了甲基吲哚洛芬。机理研究表明，选择性的H原子转移可避免许多已知的异吲哚啉酮氧化（副）产物。

  DOI：

  10.1021/acs.joc.8b01920

文献信息

• Palladium-catalyzed carbonylative cyclization of 2-bromobenzaldehyde with primary amines leading to isoindolin-1-ones
  作者：Chan Sik Cho、Wen Xiu Ren

  DOI：10.1016/j.tetlet.2009.02.109

  日期：2009.5

  2-Bromobenzaldehyde is carbonylatively cyclized with primary amines under carbon monoxide pressure in DMF at 100 °C in the presence of a catalytic amount of a palladium catalyst to give the corresponding isoindolin-1-ones in moderate to high yields.

  在催化量的钯催化剂存在下，在100℃，DMF和一氧化碳压力下，使用伯胺将2-溴苯甲醛羰基化环化，以中等至高收率得到相应的异吲哚啉-1-酮。
• Ambient Reductive Amination of Levulinic Acid to Pyrrolidones over Pt Nanocatalysts on Porous TiO₂ Nanosheets
  作者：Chao Xie、Jinliang Song、Haoran Wu、Yue Hu、Huizhen Liu、Zhanrong Zhang、Pei Zhang、Bingfeng Chen、Buxing Han

  DOI：10.1021/jacs.8b13024

  日期：2019.3.6

  Construction of N-substituted pyrrolidones from biomass-derived levulinic acid (LA) via reductive amination is a highly attractive route for biomass valorization. However, realizing this transformation using H2 as the hydrogen source under mild conditions is still very challenging. Herein, we designed porous TiO2 nanosheets-supported Pt nanoparticles (Pt/P-TiO2) as the heterogeneous catalyst. The prepared Pt/P-TiO2

  通过还原胺化从生物质衍生的乙酰丙酸 (LA) 构建 N 取代的吡咯烷酮是一种极具吸引力的生物质价值化途径。然而，在温和条件下使用 H2 作为氢源实现这种转化仍然非常具有挑战性。在此，我们设计了多孔 TiO2 纳米片负载的 Pt 纳米粒子（Pt/P-TiO2）作为多相催化剂。制备的 Pt/P-TiO2 在环境温度和 H2 压力下对 LA 的还原胺化非常有效，以生产各种 N-取代的吡咯烷酮（34 个实例）。同时，Pt/P-TiO2对乙酰丙酸酯、4-乙酰丁酸、2-乙酰苯甲酸和2-羧基苯甲醛的还原胺化显示出良好的适用性。
• One-pot synthesis of pyrrolidones from levulinic acid and amines/nitroarenes/nitriles over the Ir-PVP catalyst
  作者：Chandan Chaudhari、Masaya Shiraishi、Yoshihide Nishida、Katsutoshi Sato、Katsutoshi Nagaoka

  DOI：10.1039/d0gc01725f

  日期：——

  The synthesis of pyrrolidones via reductive amination of levulinic acid with aniline was examined over polypyrrolidone-stabilized metal nanoparticle catalysts. Among them, Ir metal was the most effective and applicable for the reductive amination of levulinic acid with nitroarenes/nitriles. Importantly, this catalyst was used for the one-pot synthesis of the anti-inflammatory drug indoprofen from 2-formylbenzoic

  吡咯烷酮的合成通过乙酰丙酸与苯胺的还原性胺化进行了检查过聚吡咯烷酮稳定的金属纳米颗粒催化剂。其中，铱金属是最有效的方法，适用于乙酰硝基/腈对乙酰丙酸的还原胺化反应。重要的是，该催化剂用于由2-甲酰基苯甲酸和2-（4-硝基苯基）丙酸一锅法合成抗炎药吲哚洛芬。
• Direct Synthesis of Lactams from Keto Acids, Nitriles, and H₂ by Heterogeneous Pt Catalysts
  作者：S. M. A. H. Siddiki、Abeda S. Touchy、Ashvini Bhosale、Takashi Toyao、Yuji Mahara、Junya Ohyama、Atsushi Satsuma、Ken-ichi Shimizu

  DOI：10.1002/cctc.201701355

  日期：2018.2.21

  We report herein the first general catalytic system for the direct synthesis of N‐substituted γ‐ and δ‐lactams by reductive amination/cyclization of keto acids (including levulinic acid) with nitriles and H2 under mild conditions (7 bar H2, 110 °C, solvent free). The most effective catalyst, Pt and MoOx co‐loaded TiO2 (Pt‐MoOx/TiO2), shows a wide substrate scope, high turnover number (TON), and good

  我们在此报告的第一一般催化系统用于直接合成的N-取代的γ-和δ-内酰胺通过酮酸（包括乙酰丙酸）与腈和H还原胺化/环化2在温和条件下（7巴ħ 2，110 °C，无溶剂）。最有效的催化剂是Pt和MoO x共负载的TiO 2（Pt-MoO x / TiO 2），具有广泛的底物范围，高周转率（TON）和良好的可重复使用性。
• Benzisothiazolinone as a useful template for the design of new monoacylglycerol lipase inhibitors: Investigation of the target residues and comparison with octhilinone
  作者：Nicolas Matuszak、Bouazza Es Saadi、Geoffray Labar、Jacqueline Marchand-Brynaert、Didier M. Lambert

  DOI：10.1016/j.bmcl.2011.10.026

  日期：2011.12

  The regulation of 2-arachidonoylglycerol (2-AG) levels is a major issue as 2-AG has been proven to participate in numerous physiopathological phenomena such as neuroprotection or analgesia. Octhilinone, a cysteine-reagent compound, has recently been shown to inhibit in the nanomolar range monoacylglycerol lipase (MAGL), the major enzyme responsible for the degradation of 2-AG. Here, we further investigate the mechanism by which octhilinone and its benzisothiazolinone analog inhibit human MAGL. We also provide new information on the structural requirements for MAGL inhibition by these compounds. Finally, we describe for N-octylbenzisothiazolinone a mode of inhibition which is partially different from that described for octhilinone, especially with regard to the targeted cysteine residues in the vicinity of the catalytic site. (C) 2011 Elsevier Ltd. All rights reserved.