7-methoxy-3-phenylisoquinoline | 667894-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 7-methoxy-3-phenylisoquinoline
• 英文别名: Methyl 3-phenyl-7-isoquinolinyl ether
• CAS: 667894-31-7
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: LSVLRXZNHHSROX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-phenylethenyl)-5-methoxybenzaldehyde 在 3-氨基吡嗪-2-碳酰肼 、 碘 作用下， 以 二甲基亚砜 为溶剂， 以85%的产率得到7-methoxy-3-phenylisoquinoline
  参考文献：
  名称：

  碘催化3-氨基吡嗪-2-碳酰肼与2-（芳乙炔基）苯甲醛的反应

  摘要：

  在60°C的DMSO中，碘催化的3-氨基吡嗪-2-碳酰肼与2-（芳基乙炔基）苯甲醛的反应导致led。将反应温度提高至100°C，氨基和酰胺基仍然不活泼，只有亚胺参与乙炔键的添加，以高收率得到2-芳基异喹啉，在无金属条件下NN键意外地断裂。

  DOI：

  10.1016/j.tet.2018.02.007

文献信息

• Alkoxide-Catalyzed Hydrosilylation of Cyclic Imides to Isoquinolines via Tandem Reduction and Rearrangement
  作者：Xiaoyu Wu、Guangni Ding、Liqun Yang、Wenkui Lu、Wanfang Li、Zhaoguo Zhang、Xiaomin Xie

  DOI：10.1021/acs.orglett.8b02287

  日期：2018.9.21

  realized via tandem reduction and rearrangement. Using TMSOK as the catalyst and (EtO)2MeSiH as the reductant, a series of cyclic imides containing different functional groups were reduced to the corresponding 3-aryl isoquinolines in moderate to good yields. The scenario of the reaction pathway was supposed to involve the reduction of imides to ω-hydroxylactams, which underwent rearrangement in the presence

  通过串联还原和重排实现了醇盐催化的环状酰亚胺氢化成异喹啉。使用TMSOK作为催化剂，使用（EtO）2 MeSiH作为还原剂，将一系列包含不同官能团的环状酰亚胺以中等至良好的产率还原为相应的3-芳基异喹啉。该反应途径的场景被认为包括将酰亚胺还原为ω-羟基内酰胺，其在碱性催化剂的存在下进行重排，然后羰基还原，然后甲硅烷氧基消除。
• Hydrophilic Pd-phosphines catalyzed one-pot synthesis of substituted isoquinolines, furopyridines and thienopyridines in aqueous medium
  作者：Veeranna Guguloth、Narasimha Swamy Thirukovela、Ramesh Balaboina、Suresh Paidakula、Ravinder Vadde

  DOI：10.1016/j.tetlet.2018.12.035

  日期：2019.1

  A first example of simple and efficient hydrophilic Pd-phosphine complexes catalyzed one-pot three-component reaction of ortho-bromo aldehydes, terminal alkynes and ammonium acetate proceeds through the tandem coupling-imination-annulation path for the synthesis of substituted isoquinolines, furopyridines and thienopyridines in good to excellent yields in green aqueous medium at mild temperature was

  简单有效的亲水性Pd-膦配合物催化邻溴代乙醛，末端炔烃和乙酸铵的单锅三组分反应的第一个例子是通过串联偶联-胺化-环化路径进行的，用于合成取代的异喹啉，呋喃吡啶和描述了噻吩并吡啶在温和的温度下在绿色水性介质中具有良好至极好的收率。
• Catalyst and additive free 6-endo-dig cyclization of ortho-alkynylarylaldimines in water: An environmentally friendly access to isoquinolines
  作者：Jin Yang、Xinyu Wei、Yajun Yu、Yeting Zhu、Yun-Hui Zhao、Wenlin Xie、Lang Zhao

  DOI：10.1016/j.tetlet.2019.151454

  日期：2020.1

  A novel and sustainable route for the synthesis of isoquinoline was developed by reacting 2-ethynylbenzaldehyde with ammonium hydroxide in water. This method provides a convenient, atom-economical, and catalyst-free access to diversely substituted isoquinolines with moderate to good yields.

  通过使2-乙炔基苯甲醛与氢氧化铵在水中反应，开发了一种新颖且可持续的异喹啉合成路线。该方法以中等到良好的产率提供了方便，原子经济，无催化剂地获得各种取代的异喹啉的方法。
• Silver Nitrate Mediated Cyclization/N–N Bond-Cleavage Reaction for the Synthesis of 3-Arylisoquinolines
  作者：Yun-Hui Zhao、Yubo Li、Mingjian Luo、Zilong Tang、Keqin Deng

  DOI：10.1055/s-0035-1562609

  日期：——

  An unprecedented silver nitrate mediated novel transformation of aromatic hydrazones into various isoquinolines has been developed. This method involves a silver nitrate promoted cyclization of aromatic hydrazones followed by N–N bond cleavage, and has wide substrate scope under mild conditions.

  已经开发出一种前所未有的硝酸银介导的芳香腙向各种异喹啉的新转化。该方法涉及硝酸银促进芳香腙环化，然后N-N键断裂，在温和条件下具有广泛的底物范围。
• Efficient Synthesis of Isoquinolines by AgNO₃-Catalyzed Sequential Imination-Annulation of 2-Alkynyl Aldehydes with Ammonium Bicarbonate
  作者：Yunhui Zhao、Mingjian Luo、Yubo Li、Xiong Liu、Zilong Tang、Keqin Deng、Gang Zhao

  DOI：10.1002/cjoc.201600277

  日期：2016.9

  An operationally simple approach for the tandem synthesis of isoquinolines by the reaction of o‐alkynylaldehydes with ammonium bicarbonate via Ag‐catalyzed 6‐endo‐dig ring closure is described. The reaction conditions and the scope of the reaction are examined, and a variety of substituted isoquinolines are prepared in moderate to excellent yields.

  描述了一种操作简单的方法，用于通过Ag催化的6-endo-dig环闭合使邻炔基醛与碳酸氢铵反应来串联合成异喹啉。检查了反应条件和反应范围，并以中等至优异的产率制备了各种取代的异喹啉。