3-methyl-8-methoxyisoquinoline | 1037219-57-0

• 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: 3-methyl-8-methoxyisoquinoline
• 英文别名: 8-methoxy-3-methylisoquinoline
• CAS: 1037219-57-0
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: BARMGYTVXFHZAW-UHFFFAOYSA-N

物化性质

• 沸点：
  301.1±22.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-8-methoxyisoquinoline 在 氢溴酸 作用下， 反应 12.0h， 以84%的产率得到3-methylisoquinolin-8-ol
  参考文献：
  名称：

  Novel synthesis of the 2-azaanthraquinone alkaloid, scorpinone, based on two microwave-assisted pericyclic reactions

  摘要：

  The total synthesis of the 2-azaanthraquinone alkaloid, scorpinone (4), isolated from the mycelium of a Bispora-like tropical fungus, has been completed in nine steps. The two key steps involve a microwave-assisted thermal electrocyclic reaction for the synthesis of an 8-oxygenated isoquinoline skeleton from a 1-aza 6 pi-hexatriene system, and a regioselective microwave- assisted [4+2] cycloaddition for the construction of a 2-azaanthraquinone framework. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.033
• 作为产物：
  描述：

  N-methoxy-1-(2-methoxy-6-prop-1-enylphenyl)methanimine 以 邻二氯苯 为溶剂， 反应 0.17h， 以71%的产率得到3-methyl-8-methoxyisoquinoline
  参考文献：
  名称：

  Novel synthesis of the 2-azaanthraquinone alkaloid, scorpinone, based on two microwave-assisted pericyclic reactions

  摘要：

  The total synthesis of the 2-azaanthraquinone alkaloid, scorpinone (4), isolated from the mycelium of a Bispora-like tropical fungus, has been completed in nine steps. The two key steps involve a microwave-assisted thermal electrocyclic reaction for the synthesis of an 8-oxygenated isoquinoline skeleton from a 1-aza 6 pi-hexatriene system, and a regioselective microwave- assisted [4+2] cycloaddition for the construction of a 2-azaanthraquinone framework. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.033

文献信息

• Palladium-Catalyzed Isoquinoline Synthesis by Tandem C–H Allylation and Oxidative Cyclization of Benzylamines with Allyl Acetate
  作者：Yujie Chen、Zhibin Huang、Chenyang Dai、Shan Yang、Da-Qing Shi、Yingsheng Zhao

  DOI：10.1021/acs.orglett.1c01153

  日期：2021.6.4

  A novel approach to synthesize 3-methylisoquinolines via a one-pot, two-step, palladium(II)-catalyzed tandem C–H allylation/intermolecular amination and aromatization is reported. A wide series of 3-methylisoquinoline derivatives were obtained directly using this method in moderate to good yields, and we highlight the synthetic importance of this new transformation.

  报道了一种通过一锅、两步、钯 (II) 催化串联 C-H 烯丙基化/分子间胺化和芳构化合成 3-甲基异喹啉的新方法。使用这种方法直接获得了一系列 3-甲基异喹啉衍生物，产率中等至良好，我们强调了这种新转化的合成重要性。
• 一种异喹啉类化合物的制备方法
  申请人：苏州大学

  公开号：CN111777553B

  公开（公告）日：2022-03-18

  本发明公开了一种异喹啉类化合物的制备方法，以草酰胺保护的苄胺和醋酸烯丙酯为原料，通过C‑H键官能团化和水解的串联反应，两步“一锅”合成得到一系列异喹啉类化合物，其所用的原料简单、易得，反应条件温和、后处理简单。
• Novel synthesis of the 2-azaanthraquinone alkaloid, scorpinone, based on two microwave-assisted pericyclic reactions
  作者：Tominari Choshi、Teppei Kumemura、Junko Nobuhiro、Satoshi Hibino

  DOI：10.1016/j.tetlet.2008.04.033

  日期：2008.6

  The total synthesis of the 2-azaanthraquinone alkaloid, scorpinone (4), isolated from the mycelium of a Bispora-like tropical fungus, has been completed in nine steps. The two key steps involve a microwave-assisted thermal electrocyclic reaction for the synthesis of an 8-oxygenated isoquinoline skeleton from a 1-aza 6 pi-hexatriene system, and a regioselective microwave- assisted [4+2] cycloaddition for the construction of a 2-azaanthraquinone framework. (C) 2008 Elsevier Ltd. All rights reserved.