ethyl 1,3-dimethylisoquinoline-4-carboxylate | 1449580-26-0

• 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: ethyl 1,3-dimethylisoquinoline-4-carboxylate
• CAS: 1449580-26-0
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: JJCRWXGJCFAFIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  重氮基乙酰乙酸乙酯 、 O-methyl acetophenone oxime 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以28%的产率得到ethyl 1,3-dimethylisoquinoline-4-carboxylate
  参考文献：
  名称：

  Rh(III)-Catalyzed Synthesis of Multisubstituted Isoquinoline and Pyridine N-Oxides from Oximes and Diazo Compounds

  摘要：

  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.

  DOI：

  10.1021/ja406338r

文献信息

• Rhodium-Catalyzed Annulation of Primary Benzylamine with α-Diazo Ketone toward Isoquinoline
  作者：Haoke Chu、Peiran Xue、Jin-Tao Yu、Jiang Cheng

  DOI：10.1021/acs.joc.6b01378

  日期：2016.9.2

  Rhodium-catalyzed annulation of commercially available primary benzylamine with α-diazo ketone was developed, leading to isoquinolines in moderate to good yields. This procedure features the employment of primary benzylamine as starting material as well as high selectivity in the 3- and 4- position of isoquinoline, generating a key compliment to the previously developed annulation with internal alkyne

  开发了铑催化的可商购的伯苄胺与α-重氮酮的环化反应，从而以中等到良好的产率产生了异喹啉。该方法的特点是采用伯苄胺作为起始原料，以及在异喹啉的3位和4位具有高选择性，这是对以前开发的内部炔烃环化反应的一个关键补充。
• Divergent Syntheses of Isoquinolines and Indolo[1,2-<i>a</i>]quinazolines by Copper-Catalyzed Cascade Annulation from 2-Haloaryloxime Acetates with Active Methylene Compounds and Indoles
  作者：Huanfeng Jiang、Jidan Yang、Xiaodong Tang、Wanqing Wu

  DOI：10.1021/acs.joc.5b02914

  日期：2016.3.4

  ligands, and excellent functional group tolerance, which makes it have potential synthetic applications. Furthermore, this strategy could also be used to enter functionalized indolo[1,2-a]quinazolines by using indoles as the counterpart of the 2-haloaryloxime acetates.

  描述了一种直接构建异喹啉的方便可靠的方法。通过2-卤代芳基肟乙酸酯与β-二酮，β-酮酸酯和β-酮腈的铜催化级联反应，合成了一系列具有高化学选择性和区域选择性的异喹啉衍生物。这种串联式成环工艺的特点是价格便宜的催化剂，不需要额外的配体以及出色的官能团耐受性，这使其具有潜在的合成应用前景。此外，通过使用吲哚作为乙酸2-卤代芳基肟的对应物，该策略还可用于进入官能化的吲哚并[1,2- a ]喹唑啉。