8-methoxy-2-phenyl-5,6-dihydrobenzo[f]isoquinoline | 1541898-13-8

• 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: 8-methoxy-2-phenyl-5,6-dihydrobenzo[f]isoquinoline
• 英文别名: 8-Methoxy-2-phenyl-5,6-dihydrobenzo[f]isoquinoline
• CAS: 1541898-13-8
• 化学式: C₂₀H₁₇NO
• 分子量: 287.361
• InChiKey: XPEFDVJUULMDNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  6-methoxy-1-(phenylethynyl)-3,4-dihydronaphthalene-2-carbaldehyde 在 苄脒盐酸盐 、 三乙胺 作用下， 140.0 ℃ 、1.4 MPa 条件下， 反应 0.08h， 以86%的产率得到8-methoxy-2-phenyl-5,6-dihydrobenzo[f]isoquinoline
  参考文献：
  名称：

  通过铜（i）催化的多组分反应 有效合成异喹啉和吡啶†

  摘要：

  通过无配体铜催化的β-卤代戊基/芳基三组分反应，高收率合成了多种3-取代的异喹啉，甾族吡啶，5,6-二氢苯并[ f ]异喹啉和1,6-萘吡啶微波辐射下，DMF中的乙醛，芳族/脂肪族末端炔烃和叔丁胺/苯甲m 微波辐射下邻炔基芳基/乙烯基醛与苯甲idine的无催化剂反应也以优异的产率提供了3-取代的异喹啉和取代的吡啶衍生物。

  DOI：

  10.1039/c3ra46722h

文献信息

• Efficient synthesis of isoquinolines and pyridines via copper(i)-catalyzed multi-component reaction
  作者：Kommuri Shekarrao、Partha Pratim Kaishap、Sanjib Gogoi、Romesh C. Boruah

  DOI：10.1039/c3ra46722h

  日期：——

  A wide range of 3-substituted isoquinolines, steroidal pyridines, 5,6-dihydrobenzo[f]isoquinolines and 1,6-naphthyridine were synthesized in good yield via a ligand-free copper-catalyzed three-component reaction of β-halovinyl/aryl aldehyde, aromatic/aliphatic terminal alkyne and tert-butylamine/benzamidine in DMF under microwave irradiation. A catalyst-free reaction of ortho-alkynyl aryl/vinyl aldehydes

  通过无配体铜催化的β-卤代戊基/芳基三组分反应，高收率合成了多种3-取代的异喹啉，甾族吡啶，5,6-二氢苯并[ f ]异喹啉和1,6-萘吡啶微波辐射下，DMF中的乙醛，芳族/脂肪族末端炔烃和叔丁胺/苯甲m 微波辐射下邻炔基芳基/乙烯基醛与苯甲idine的无催化剂反应也以优异的产率提供了3-取代的异喹啉和取代的吡啶衍生物。
• One-pot synthesis of isoquinoline and related compounds via Cu-mediated tandem cross-coupling and cyclization
  作者：Shubhendu Dhara、Raju Singha、Yasin Nuree、Jayanta K. Ray

  DOI：10.1016/j.tetlet.2013.11.088

  日期：2014.1

  One-pot synthetic strategy has been developed to access isoquinolines and its analogs via Cu-mediated tandem cross-coupling and cyclization in good yields under mild reaction conditions. A mixture of suitably substituted α-bromoaldehyde, terminal alkyne, and aq NH3 in CuI/1,10-phenanathroline catalytic system afforded the 3-substituted isoquinoline regio-selectively in good to excellent yields.

  已经开发出一锅合成策略，以在温和的反应条件下通过铜介导的串联交叉偶联和环化以高收率获得异喹啉及其类似物。在CuI / 1，10-菲咯啉催化体系中适当取代的α-溴醛，末端炔烃和NH 3水溶液的混合物以良好或优异的收率选择性地生成3-取代的异喹啉。
• An efficient synthesis of pyrrole and fluorescent isoquinoline derivatives using NaN3/NH4Cl promoted intramolecular aza-annulation
  作者：Akash Jana、Susanta Kumar Manna、Suresh Kumar Mondal、Arabinda Mandal、Saikat Kumar Manna、Avijit Jana、Bidyut Kumar Senapati、Manas Jana、Shubhankar Samanta

  DOI：10.1016/j.tetlet.2016.07.002

  日期：2016.8

  An efficient synthetic protocol of pyrroles and isoquinolines through NaN3/NH4Cl promoted intramolecular aza-annulation of formyl group with suitable alkenes or alkynes is described in high yield and regioselectivities. The metal free exo-trig and endo-dig aza-cyclisation has been extended for the synthesis of bicyclic or tricyclic pyrroles along with environment sensitive fluorescent isoquinoline

  以高收率和区域选择性描述了通过NaN 3 / NH 4 Cl促进的甲酰基分子内氮杂环化与合适的烯烃或炔烃的吡咯和异喹啉的有效合成方案。无金属外型- trig的和内切-挖氮杂环化已扩展为二环或三环的吡咯与环境敏感的荧光异喹啉衍生物沿合成。反应发生的产率高，范围广且对官能团的耐受性高。lamellarin Q核心结构的简短合成证明了该方法的合成效用。
• Urea‐Promoted Neat Synthesis of Fused Dihydroisoquinolines and Disubstituted Pyridines: A Mechanistic Observation with Molecular‐Sensing Studies
  作者：Sk Abulkalam Azad、Anirban Bera、Jayanta Samanta、Nayim Sepay、Rathin Jana、Chandan Kumar Pal、Mijanur Rahaman Molla、Debabrata Maiti、Shubhankar Samanta

  DOI：10.1002/chem.202303287

  日期：2024.3

  A concise and efficient synthesis of fused isoquinolines has been established by using an environmentally friendly neat approach. In this method, the electrocyclic reaction is emphasized over the typical aza-Michael addition. This green methodology allows the synthesis of various isoquinolines, including the alkaloid decumbenine B and a fluorophore that selectively detects picric acid.

  通过使用环境友好的纯净方法，建立了稠合异喹啉的简洁有效的合成方法。在该方法中，电环反应比典型的氮杂迈克尔加成更重要。这种绿色方法可以合成各种异喹啉，包括生物碱 decumbenine B 和选择性检测苦味酸的荧光团。