(E)-3,4-diphenyl-1-styrylisoquinoline | 1257846-42-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E)-3,4-diphenyl-1-styrylisoquinoline
• 英文别名: 3,4-diphenyl-1-[(E)-2-phenylethenyl]isoquinoline
• CAS: 1257846-42-6
• 化学式: C₂₉H₂₁N
• 分子量: 383.492
• InChiKey: IKBKWBBJMBYAMN-QZQOTICOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-(3-azidoprop-1-ene-1,3-diyl)dibenzene 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 (E)-3,4-diphenyl-1-styrylisoquinoline
  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

• Rhodium(III)-Catalyzed Synthesis of Isoquinolines from Aryl Ketone<i>O</i>-Acyloxime Derivatives and Internal Alkynes
  作者：Pei Chui Too、Yi-Feng Wang、Shunsuke Chiba

  DOI：10.1021/ol102504b

  日期：2010.12.17

  isoquinolines from aryl ketone O-acyloxime derivatives and internal alkynes has been developed using [Cp*RhCl2]2−NaOAc as the potential catalyst system. The present transformation is carried out by a redox-neutral sequence of C−H vinylation via ortho-rhodation and C−N bond formation of the putative vinyl rhodium intermediate on the oxime nitrogen, where the N−O bond of oxime derivatives could work as an internal

  利用[Cp * RhCl 2 ] 2 -NaOAc作为潜在的催化剂体系，开发了一种由芳基酮O-酰基肟衍生物和内部炔烃合成异喹啉的方法。目前的转化是通过肟化氮的氧化还原-中性序列，通过肟基氮上的假定铑乙烯基中间体在邻位上的邻位R-rhodation和C-N键形成的，其中肟衍生物的N-O键可以用作内部氧化剂以维持催化循环。
• Synthesis of Isoquinolines and Heterocycle-Fused Pyridines via Three-Component Cascade Reaction of Aryl Ketones, Hydroxylamine, and Alkynes
  作者：Liyao Zheng、Jia Ju、Yunhui Bin、Ruimao Hua

  DOI：10.1021/jo3010414

  日期：2012.7.6

  An efficient one-pot synthesis of isoquinolines and heterocycle-fused pyridines by three-component reaction of aryl ketones, hydroxylamine, and alkynes is developed. The reaction involves condensation of aryl ketones and hydroxylamine, rhodium(III)-catalyzed C–H bond activation of the in situ generated aryl ketone oximes, and cyclization with internal alkynes. This protocol enables rapid assembly of

  通过芳基酮，羟胺和炔烃的三组分反应，有效地一锅法合成异喹啉和杂环稠合吡啶。该反应涉及芳基酮和羟胺的缩合，铑（III）催化原位生成的芳基酮肟的C–H键活化以及与内部炔烃的环化作用。该协议能够从容易获得的底物中快速组装多取代的异喹啉以及γ-咔啉，呋喃[2,3- c ]吡啶，噻吩并[2,3- c ]吡啶和苯并呋喃[2,3- c ]吡啶。
• C–H Activation Guided by Aromatic N–H Ketimines: Synthesis of Functionalized Isoquinolines Using Benzyl Azides and Alkynes
  作者：Sreya Gupta、Junghoon Han、Yongjin Kim、Soon W. Lee、Young Ho Rhee、Jaiwook Park

  DOI：10.1021/jo501465q

  日期：2014.10.3

  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.