methyl 1-methyl-3-phenylisoquinoline-4-carboxylate | 1314243-17-8

• 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: methyl 1-methyl-3-phenylisoquinoline-4-carboxylate
• CAS: 1314243-17-8
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: CAFJBBPCEYMBLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-叠氮基乙基苯 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 ([2,5-Me2-3,4-Ph2(η5-C4CNHPh)]Ru(CO)(μ-CO))2 、 copper diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 methyl 1-methyl-3-phenylisoquinoline-4-carboxylate
  参考文献：
  名称：

  C–H Activation Guided by Aromatic N–H Ketimines: Synthesis of Functionalized Isoquinolines Using Benzyl Azides and Alkynes

  摘要：

  Aromatic N-H ketimines were in situ generated from various benzylic azides by ruthenium catalysis for the subsequent Rh-catalyzed annulation reaction with alkynes to give the corresponding isoquinolines. In contrast to conventional synthetic methods for aromatic NH ketimines, our protocol works under mild and neutral conditions, which enabled the synthesis of isoquinolines having various functionalities such as carbonyl, ester, alkenyl, and ether groups. In addition, the imidates generated from alpha-azido ethers were successfully used for the synthesis of 1-alkoxyisoquinolines.

  DOI：

  10.1021/jo501465q

文献信息

• Rh(III)-catalyzed synthesis of isoquinolines using the N-Cl bond of N-chloroimines as an internal oxidant
  作者：Bing Qi、Lili Fang、Qi Wang、Shan Guo、Pengfei Shi、Benfa Chu、Jin Zhu

  DOI：10.1016/j.tetlet.2020.151771

  日期：2020.4

  The Rh(III)-catalyzed coupling of N-chloroimines with alkynes for the efficient synthesis of isoquinolines is reported. This represents the first use of the N-Cl bond of N-chloroimines as an internal oxidant for construction of the isoquinoline skeleton. The synthesis features atom and step economy, a green solvent (EtOH), mild reaction conditions, and a broad substrate scope.2020 Elsevier Ltd. All

  报道了Rh（III）催化的N-氯亚胺与炔烃的偶联，用于有效合成异喹啉。这表示在第一次使用的N-Cl键的Ñ -chloroimines作为用于构建异喹啉骨架的内部氧化剂。该合成具有原子和步骤经济性，绿色溶剂（EtOH），温和的反应条件和广泛的底物范围。2020Elsevier Ltd.保留所有权利
• Synthesis of Isoquinolines from α-Aryl Vinyl Azides and Internal Alkynes by Rh-Cu Bimetallic Cooperation
  作者：Yi-Feng Wang、Kah Kah Toh、Jian-Yuan Lee、Shunsuke Chiba

  DOI：10.1002/anie.201101009

  日期：2011.6.20

  Catalysts in a relay: A synthetic method for delivering highly substituted isoquinolines has been developed (see scheme; Cp*=C5Me5, DMF=N,N‐dimethylformamide, TEMPO=2,2,6,6‐tetramethylpiperidine‐1‐oxyl). A preliminary mechanistic study showed that the rhodium and copper cooperate synergistically in the multistep sequence.

  继电器中的催化剂：已开发出一种用于合成高度取代的异喹啉的合成方法（参见方案; Cp * = C 5 Me 5，DMF = N，N-二甲基甲酰胺，TEMPO = 2,2,6,6-四甲基哌啶-1-氧基）。初步的机理研究表明，铑和铜在多步骤序列中协同协同作用。