6-methoxy-3,4-diphenyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one | 1604839-46-4

• 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: 6-methoxy-3,4-diphenyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one
• CAS: 1604839-46-4
• 化学式: C₃₁H₂₂N₂O₂
• 分子量: 454.528
• InChiKey: GEIJLGIBNSIHTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,4-dimethoxy-N-(quinolin-8-yl)benzamide 、 二苯基乙炔 在 bis(1,5-cyclooctadiene)nickel (0) 、 三苯基膦 、 lithium tert-butoxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以66%的产率得到6-methoxy-3,4-diphenyl-2-(quinolin-8-yl)isoquinolin-1(2H)-one
  参考文献：
  名称：

  镍催化 Csp2-OMe 功能化用于化学选择性芳族同源化纳米石墨烯

  摘要：

  Ni(0) 催化的方法在内部炔烃存在下有效地实现了 C sp2 -OMe 官能化，从而化学选择性地形成芳族同系物或分子内单环化产物。此外，芳香族同系化产物被证明是有效的前体，可进一步向类纳米石墨烯合成多样化。

  DOI：

  10.1002/chem.202200625

文献信息

• Cobalt-catalyzed cyclization of benzamides with alkynes: a facile route to isoquinolones with hydrogen evolution
  作者：Ramasamy Manoharan、Masilamani Jeganmohan

  DOI：10.1039/c8ob01924j

  日期：——

  benzamides with alkynes assisted by an 8-aminoquinoline ligand in the presence of Co(OAc)2·4H2O and pivalic acid under an air atmosphere provided isoquinolone derivatives in good to excellent yields. In this reaction, the active Co(III) species is regenerated by the reaction of Co(I) species with pivalic acid under an air atmosphere with hydrogen evolution. The proposed mechanism was supported by competition

  在Co（OAc）2 ·4H 2 O和新戊酸的存在下，在空气气氛下，苯甲酰胺与炔烃在8-氨基喹啉配体的辅助下，以良好或极好的收率提供了异​​喹诺酮衍生物。在该反应中，活性Co（III）物种是通过Co（I）物种与新戊酸在空气中有氢气逸出的条件下反应而再生的。竞争实验，氘标记研究，自由基清除剂实验和动力学研究为拟议的机制提供了支持。
• Ruthenium-Catalyzed Synthesis of Isoquinolones with 8-Aminoquinoline as a Bidentate Directing Group in C–H Functionalization
  作者：Srinivasarao Allu、K. C. Kumara Swamy

  DOI：10.1021/jo500424p

  日期：2014.5.2

  Ruthenium-catalyzed oxidative annulation of N-quinolin-8-yl-benzamides with alkynes in open air has been achieved using 8-aminoquinolinyl moiety as a bidentate directing group in the presence of Cu(OAc)(2)center dot H2O as an oxidant. This reaction offers a broad substrate scope, and both symmetrical and unsymmetrical alkynes can be applied. High regioselectivity was achieved in the case of unsymmetrical (aryl)alkynes. Reaction with heteroaryl amides was also successful in this catalytic process. A ruthenium-N-quinolin-8-yl-benzamide complex was isolated in the absence of alkyne; in the absence of both N-quinolin-8-yl-benzamide and alkyne, in contrast to literature, only the monoacetate complex RuCl(OAc)(p-cymene), but not the bis-acetate complex Ru(OAc)2(p-cymene), was isolated. These data suggest that this reaction may proceed via N,N-bidentate chelate complex. Key products were characterized by X-ray crystallography.