3-(naphthalen-2-yl)-2-phenylisoquinolin-1(2H)-one | 1448450-27-8

• 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-(naphthalen-2-yl)-2-phenylisoquinolin-1(2H)-one
• 英文别名: 3-Naphthalen-2-yl-2-phenylisoquinolin-1-one；3-naphthalen-2-yl-2-phenylisoquinolin-1-one
• CAS: 1448450-27-8
• 化学式: C₂₅H₁₇NO
• 分子量: 347.416
• InChiKey: ANXLQOQBGMCCQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 水 、 copper(II) acetate monohydrate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以48 mg的产率得到3-(naphthalen-2-yl)-2-phenylisoquinolin-1(2H)-one
  参考文献：
  名称：

  铜催化 2-(1-炔基)苯扎二亚胺与水串联反应构建异喹啉-1(2H)-酮

  摘要：

  开发了 Cu(OAc)2 催化的 2-(1-炔基) 苯并二亚胺与水的串联反应，用于合成异喹啉-1(2H)-酮。此外，只需在反应体系中加入 N-卤代琥珀酰亚胺（NXS：X = Cl、Br、I），即可以良好的收率获得 4-卤素取代的异喹啉-1(2H)-酮。机理研究表明，该反应可能是由 2-(1-炔基) 苯扎二亚胺的高度区域选择性分子内环化引发的，生成相应的异喹啉鎓中间体。

  DOI：

  10.1002/ejoc.201500908

文献信息

• Solvent-Switched Benzylic Methylene Functionalization: Addition, Ring-Opening, Cyclization, and Unexpected Cleavage of C–O and C–C Bonds
  作者：Deng Yuan Li、Xue Song Shang、Guo Rong Chen、Pei Nian Liu

  DOI：10.1021/ol401470y

  日期：2013.8.2

  been achieved using imines as reagents and potassium tert-butoxide as the catalyst. Depending on the solvent used, the reaction proceeds by two pathways. In THF, an addition/elimination reaction of exo-cyclic enol ethers with imines provides dihydroisobenzofuran derivatives in good yield. In DMSO, an addition/ring-opening/cyclization cascade reaction occurs with unexpected cleavage of C–O and C–C bonds

  使用亚胺作为试剂并使用叔丁醇钾作为催化剂，可以实现环外烯醇醚的分子间苄基亚甲基官能化。根据所使用的溶剂，反应通过两个途径进行。在THF中，的加成/消除反应外切-环烯醇醚与亚胺提供以良好的收率二氢异苯并呋喃衍生物。在DMSO中，加成/开环/环化级联反应会发生意外的C–O和C–C键断裂，从而在环境反应条件下以高收率提供异喹啉-1（2 H）-一产品。
• Electrochemical annulation of 1,2,3-benzotriazinones with alkynes to access isoquinolin-1(2<i>H</i>)-ones
  作者：JinKang Chen、Linxia Xiao、Liang Qi

  DOI：10.1039/d3ob01161e

  日期：——

  for electrochemical radical cascade annulation of 1,2,3-benzotriazinones with alkynes is described. Under catalyst-free and external reductant-free electrolysis conditions, a range of isoquinolin-1(2H)-ones were obtained in moderate to good yields. Cyclic voltammetry and control studies suggest that the reaction proceeds via a radical pathway. Furthermore, this approach could be easily scaled up.

  描述了 1,2,3-苯并三嗪酮与炔烃的电化学自由基级联成环的环保方法。在无催化剂和无外部还原剂的电解条件下，以中等至良好的收率获得了一系列异喹啉-1(2 H )-酮。循环伏安法和对照研究表明该反应通过自由基途径进行。此外，这种方法可以很容易地扩大规模。
• Transition Metal-Free Cascade Reactions of Alkynols to Afford Isoquinolin-1(2<i>H</i>)-one and Dihydroisobenzofuran Derivatives
  作者：Deng Yuan Li、Ke Ji Shi、Xiao Feng Mao、Guo Rong Chen、Pei Nian Liu

  DOI：10.1021/jo5006312

  日期：2014.5.16

  Transition metal-free cascade reactions of alkynols with imines have been achieved using potassium tert-butoxide as catalyst. Switching the reaction solvent gives two kinds of products in good yield: isoquinolin-1(2H)-one derivatives and dihydroisobenzofuran derivatives. This approach was used to generate the natural product 8-oxypseudopalmatine in a two-step procedure from commercially available starting materials. Additionally, multicomponent reactions of alkynols, aldehydes, and amines were also successfully achieved to afford isoquinolin-1(2H)-one derivatives.
• Construction of Isoquinolin-1(2<i>H</i>)-ones by Copper-Catalyzed Tandem Reactions of 2-(1-Alkynyl)benzaldimines with Water
  作者：Mingliang Zhang、Hui-Jun Zhang、Wenqing Ruan、Ting-Bin Wen

  DOI：10.1002/ejoc.201500908

  日期：2015.9

  The Cu(OAc)2-catalyzed tandem reaction of 2-(1-alkynyl)benzaldimines with water for the synthesis of isoquinolin-1(2H)-ones was developed. Moreover, 4-halogen-substituted isoquinolin-1(2H)-ones were obtained in good yields simply by including N-halosuccinimides (NXS: X = Cl, Br, I) in the reaction system. Mechanistic studies indicated that the reactions are probably initiated by highly regioselective

  开发了 Cu(OAc)2 催化的 2-(1-炔基) 苯并二亚胺与水的串联反应，用于合成异喹啉-1(2H)-酮。此外，只需在反应体系中加入 N-卤代琥珀酰亚胺（NXS：X = Cl、Br、I），即可以良好的收率获得 4-卤素取代的异喹啉-1(2H)-酮。机理研究表明，该反应可能是由 2-(1-炔基) 苯扎二亚胺的高度区域选择性分子内环化引发的，生成相应的异喹啉鎓中间体。