3,4-diphenyl-2-(quinolin-8-yl)-6-(trifluoromethyl)isoquinolin-1(2H)-one | 1604839-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,4-diphenyl-2-(quinolin-8-yl)-6-(trifluoromethyl)isoquinolin-1(2H)-one
• CAS: 1604839-50-0
• 化学式: C₃₁H₁₉F₃N₂O
• 分子量: 492.5
• InChiKey: VOKZGUJMRJLUTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.89
• 重原子数：
  37.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  8-氨基喹啉 、 4-三氟甲基苯甲酰氯 在 4-二甲氨基吡啶 、 manganese(II) acetate 、 cobalt(II) diacetate tetrahydrate 、 特戊酸钠 、 三乙胺 作用下， 以 二氯甲烷 、 2,2,2-三氟乙醇 为溶剂， 反应 6.0h， 生成 3,4-diphenyl-2-(quinolin-8-yl)-6-(trifluoromethyl)isoquinolin-1(2H)-one
  参考文献：
  名称：

  钴催化的氨基喹啉引导的炔烃 C(sp2)?H 键烯基化

  摘要：

  开发了一种钴催化、氨基喹啉和吡啶酰胺引导的炔烃 C(sp 2 )  H 键烯基化方法。该方法显示出优异的官能团耐受性，内部和末端炔烃都是偶联的有效底物。该反应采用Co(OAc) 2 ⋅4 H 2 O催化剂、Mn(OAc) 2助催化剂和氧气（来自空气）作为终端氧化剂。

  DOI：

  10.1002/anie.201404579

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.