3,4-diphenyl-6-(trifluoromethyl)isoquinolin-1(2H)-one | 1360651-30-4

• 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: 3,4-diphenyl-6-(trifluoromethyl)isoquinolin-1(2H)-one
• 英文别名: 3,4-Diphenyl-6-trifluoromethylisoquinoline-1(2H)-one；3,4-diphenyl-6-(trifluoromethyl)-2H-isoquinolin-1-one
• CAS: 1360651-30-4
• 化学式: C₂₂H₁₄F₃NO
• 分子量: 365.354
• InChiKey: IKKYMQQTQMPTKY-UHFFFAOYSA-N

物化性质

• 沸点：
  532.0±50.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-diphenyl-6-(trifluoromethyl)isoquinolin-1(2H)-one 、 对苯醌 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 sodium acetate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以99%的产率得到12'-phenyl-2'-(trifluoromethyl)-5'H-spiro[cyclohex[3]ene-1,7'-isoindolo[2,1-b]isoquinoline]-2,5,5'-trione
  参考文献：
  名称：

  Ir(III)-Catalyzed Oxidative Coupling of NH Isoquinolones with Benzoquinone

  摘要：

  The oxidative coupling reactions of NH isoquinolones with 1,4-benzoquinone proceeded efficiently to form spiro compounds in the presence of an Ir(III) catalyst through C-H activation. The reactions have a broad range of substrates, with nearly quantitative yields, without the use of external oxidants. For 1,4-naphthoquinone and other substituted 1,4-benzoquinone the reactions also gave high yields with Cu(OAc)(2)center dot H2O as an external oxidant. A catalytically competent five-membered iridacycle has been isolated and structurally characterized, thus revealing a key intermediate in the catalytic cycle.

  DOI：

  10.1021/acs.orglett.5b01974
• 作为产物：
  描述：

  N-chloro-4-trifluoromethylbenzamide 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 zinc diacetate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 14.0h， 生成 3,4-diphenyl-6-(trifluoromethyl)isoquinolin-1(2H)-one
  参考文献：
  名称：

  Sulfilimines as Transformable and Retainable Directing Groups in Rhodium-Catalyzed ortho-C–H Bond Functionalization

  摘要：

  DOI：

  10.1021/acs.orglett.2c02630

文献信息

• Ruthenium-Catalyzed Isoquinolone Synthesis through CH Activation Using an Oxidizing Directing Group
  作者：Bin Li、Huiliang Feng、Shansheng Xu、Baiquan Wang

  DOI：10.1002/chem.201102445

  日期：2011.11.4

  The oxidant directs: A mild, practical, efficient, and regioselective Ru‐catalyzed isoquinolone synthesis with a broad substrate scope was reported (see scheme). In this redox neutral process, the aromatic CH bond functionalization can be performed at room temperature without using any external oxidant. The mechanism of the reaction was probed, and it was found that CH activation is the turnover‐limiting

  氧化剂的方向：据报道，该方法温和，实用，有效且具有区域选择性，Ru催化的异喹诺酮合成具有广泛的底物范围（参见方案）。在这种氧化还原中性工艺中，可以在室温下进行芳族CH键官能化，而无需使用任何外部氧化剂。探究了反应的机理，发现CH活化是限制周转的步骤。
• Cobalt-Catalyzed Cyclization of <i>N</i> -Methoxy Benzamides with Alkynes using an Internal Oxidant through C−H/N−O Bond Activation
  作者：Ganesan Sivakumar、Arjun Vijeta、Masilamani Jeganmohan

  DOI：10.1002/chem.201600471

  日期：2016.4.18

  The cyclization of substituted N‐methoxy benzamides with alkynes in the presence of an easily affordable cobalt complex and NaOAc provides isoquinolone derivatives in good to excellent yields. The cyclization reaction is compatible with a range of functional group‐substituted benzamides, as well as ester‐ and alcohol‐substituted alkynes. The cobalt complex [CoIIICp*(OR)2] (R=Me or Ac) serves as an

  在容易负担得起的钴络合物和NaOAc的存在下，用炔烃将取代的N-甲氧基苯甲酰胺环化，可以提供高至优异收率的异喹诺酮衍生物。环化反应与各种官能团取代的苯甲酰胺以及酯和醇取代的炔烃兼容。钴配合物[Co III Cp *（OR）2 ]（R = Me或Ac）可作为有效的环化反应催化剂。后来，在POCl 3或PBr 3的存在下，异喹诺酮衍生物以极高的收率转化为1-氯和1-溴取代的异喹啉衍生物。
• <i>N</i>-Sulfonylcarboxamide as an Oxidizing Directing Group for Ruthenium-Catalyzed C-H Activation/Annulation
  作者：Elina Petrova、Dace Rasina、Aigars Jirgensons

  DOI：10.1002/ejoc.201601582

  日期：2017.4.3

  N-Sulfonylcarboxamides can act as both a directing group for C–H activation and an internal oxidant in the Ru-catalyzed annulation reaction with alkynes to give isoquinolones. Of all of the N-sulfonylcarboxamides that were studied, the N-(2,6-difluorophenyl)sulfonamide derivatives were found to be the most efficient and led to the formation of an unstable sulfinate byproduct that decomposed into 1

  N-磺酰基甲酰胺既可以作为 C-H 活化的导向基团，也可以作为 Ru 催化的炔烃环化反应中的内部氧化剂，以产生异喹诺酮。在研究的所有 N-磺酰甲酰胺中，发现 N-(2,6-二氟苯基)磺酰胺衍生物最有效，并导致形成不稳定的亚磺酸盐副产物，在反应条件。所描述的异喹诺酮合成为目前已知的异羟肟酸和亚砜亚胺衍生物的无痕环化提供了替代方案。
• Palladium‐Catalyzed Inert C−H Bond Activation and Cyclocarbonylation of Isoquinolones with Carbon Dioxide Leading to Isoindolo[2,1‐ <i>b</i> ]isoquinoline‐5,7‐Diones
  作者：Kelu Yan、Junbin Jin、Yong Kong、Bin Li、Baiquan Wang

  DOI：10.1002/adsc.201900305

  日期：2019.7.2

  A palladium‐catalyzed inert C−H bond activation and cyclocarbonylation of isoquinolones leading to isoindolo[2,1‐b]isoquinoline‐5,7‐diones under 1 atm of carbon dioxide has been developed. This transformation features high regio‐ and chemo‐selectivity, step‐economy, and good functional group tolerance. Most of the corresponding products were obtained in moderate to good yields. It offers an alternative

  已开发出在1个大气压的二氧化碳下，钯催化的惰性C-H键活化和异喹诺酮的环羰基化反应，导致异吲哚并[2,1 – b ]异喹啉-5,7-二酮。这种转变具有很高的区域选择性和化学选择性，逐步经济性和良好的官能团耐受性。大部分相应的产品以中等到良好的产率获得。它为合成有用的多种异吲哚并[2,1 - b ]异喹啉-5,7-二酮衍生物提供了另一种方法。
• Rhodium-catalyzed C–H activation of hydrazines leads to isoquinolones with tunable aggregation-induced emission properties
  作者：Bole Yu、Ying Chen、Mei Hong、Pingping Duan、Shifeng Gan、Hui Chao、Zujin Zhao、Jing Zhao

  DOI：10.1039/c5cc05239d

  日期：——

  We report a Rh^III-catalyzed synthesis of isoquinolonesviaC–H activation/annulation of benzoylhydrazines and alkynes for AIE studies.

  我们报道了一种Rh^III催化的合成方法，通过苯甲酰肼和炔烃的C-H活化/环化反应合成异喹啉，用于AIE研究。