4-(ethoxycarbonyl)-1,3-dimethylisoquinoline 2-oxide | 1449579-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 4-(ethoxycarbonyl)-1,3-dimethylisoquinoline 2-oxide
• 英文别名: Ethyl 1,3-dimethyl-2-oxidoisoquinolin-2-ium-4-carboxylate；ethyl 1,3-dimethyl-2-oxidoisoquinolin-2-ium-4-carboxylate
• CAS: 1449579-93-4
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: SMZUUFUARQDAEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙酮 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 盐酸羟胺 、 sodium acetate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 12.0h， 生成 4-(ethoxycarbonyl)-1,3-dimethylisoquinoline 2-oxide
  参考文献：
  名称：

  Ir(III)-Catalyzed Synthesis of Isoquinoline N-Oxides from Aryloxime and α-Diazocarbonyl Compounds

  摘要：

  An efficient Ir(III)-catalyzed C-H activation and annulations of aryloxime with a-diazocarbonyl compounds has been developed for the synthesis of substituted isoquinoline N-oxides. The reaction proceeds under mild atmospheric conditions, without any external oxidants and releases N-2 and H2O as the byproducts. In addition, synthetic applications of the N-oxide products have been established by performing further functionalization. An interesting dimeric iridacyclic complex allied through a bis-silver carboxylate bridge has been isolated that efficiently catalyzed the reaction.

  DOI：

  10.1021/acs.orglett.5b03462

文献信息

• Copper‐Catalyzed C(<i>sp</i>³)− Functionalization and Annulation of 2‐Bromoaryl Oximes with Active Methylene Compounds towards Synthesis of Isoquinoline <i>N</i>‐Oxides
  作者：Chandresh K. Patel、Raghuram Gujjarappa、Kamal Kant、Susanta Ghanta、Virender Singh、Arup K. Kabi、Nabil Al‐Zaqri、Chandi C. Malakar

  DOI：10.1002/adsc.202300217

  日期：2023.7.4

  (II)-catalyzed C(sp3)− functionalization of β-diketones/β-ketoesters with 2-bromobenzaldehyde oximes followed by the intramolecular cyclization of in situ generated acylated intermediates to deliver isoquinoline N-oxides. The copper(II) acetate catalyzed C−H functionalization showed maximum efficacy at 60 °C in methanol/toluene as solvent. The described reaction conditions were applicable over a wide range of

  所建立的过程通过铜 (II) 催化的β-二酮/ β-酮酯与 2-溴苯甲醛肟的C( sp 3 )− 官能化，然后原位生成的酰化中间体进行分子内环化，以提供异喹啉N-氧化物。乙酸铜 (II) 催化的 CH 官能化在 60 °C、以甲醇/甲苯为溶剂中显示出最大功效。所描述的反应条件适用于具有多种官能团的多种底物，以产生异喹啉N-氧化物，产率高达85%。通过控制实验和 DFT 计算进一步阐明了所开发的方法。
• Rh(III)-Catalyzed Synthesis of Multisubstituted Isoquinoline and Pyridine <i>N</i>-Oxides from Oximes and Diazo Compounds
  作者：Zhuangzhi Shi、Dennis C. Koester、Mélissa Boultadakis-Arapinis、Frank Glorius

  DOI：10.1021/ja406338r

  日期：2013.8.21

  Multisubstituted isoquinoline and pyridine N-oxides have been prepared by Rh(III)-catalyzed cyclization of oximes and diazo compounds via aryl and vinylic C-H activation. This intermolecular annulation involving tandem C-H activation, cyclization, and condensation steps proceeds under mild conditions, obviates the need for oxidants, releases N-2 and H2O as the byproducts, and displays a broad substituent scope.
• Ir(III)-Catalyzed Synthesis of Isoquinoline <i>N</i>-Oxides from Aryloxime and α-Diazocarbonyl Compounds
  作者：Ravindra S. Phatake、Pitambar Patel、Chepuri V. Ramana

  DOI：10.1021/acs.orglett.5b03462

  日期：2016.1.15

  An efficient Ir(III)-catalyzed C-H activation and annulations of aryloxime with a-diazocarbonyl compounds has been developed for the synthesis of substituted isoquinoline N-oxides. The reaction proceeds under mild atmospheric conditions, without any external oxidants and releases N-2 and H2O as the byproducts. In addition, synthetic applications of the N-oxide products have been established by performing further functionalization. An interesting dimeric iridacyclic complex allied through a bis-silver carboxylate bridge has been isolated that efficiently catalyzed the reaction.