5-fluoro-3,4-diphenylisoquinolin-1(2H)-one | 1312991-49-3

• 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: 5-fluoro-3,4-diphenylisoquinolin-1(2H)-one
• CAS: 1312991-49-3
• 化学式: C₂₁H₁₄FNO
• 分子量: 315.347
• InChiKey: FFVQDKHNAGLNCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  丙烯酸苄酯 、 5-fluoro-3,4-diphenylisoquinolin-1(2H)-one 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以41%的产率得到benzyl 2-(1-fluoro-5-oxo-12-phenyl-7H-isoindolo[2,1-b]isoquinolin-7-yl)acetate
  参考文献：
  名称：

  Oxidative Coupling of NH Isoquinolones with Olefins Catalyzed by Rh(III)

  摘要：

  Rh(III)-catalyzed oxidative coupling reactions between isoquinolones with 3-aryl groups and activated olefins have been achieved using anhydrous Cu(OAc)(2) as an oxidant to give tetracyclic products. The nitrogen atom acts as a directing group to facilitate ortho C-H activation. This reaction can be one-pot starting from methyl benzohydroxamates, without the necessity of the isolation of isoquinolone products. Abroad scope of substrates has been demonstrated, and both terminal and internal activated olefins can be applied. In the coupling of N-methylmaleimide, a Wacker-like mechanism was proposed, where backside attack of the NH group in isoquinolones is suggested as a key step. Selective C-H activation has also been achieved at the 8-position of 1-naphthol, leading to an olefination product.

  DOI：

  10.1021/jo2002209
• 作为产物：
  描述：

  3-氟-N-羟基苯甲酰胺 、 二苯基乙炔 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 potassium 3-(trifluoromethyl)benzoate 作用下， 以 水 为溶剂， 反应 18.0h， 以58%的产率得到5-fluoro-3,4-diphenylisoquinolin-1(2H)-one
  参考文献：
  名称：

  钌（II）催化H 2 O中的脱水C–H / N–OH官能化：羧酸盐配体的细微作用和机理研究

  摘要：

  衍生自缺电子芳族羧酸3-（F 3 C）C 6 H 4 CO 2 H的钌（II）络合物被证明是通过水中不含NH的异羟肟酸使炔烃脱水的高效催化剂。C–H / N–OH官能化具有出色的位置选择性以及充足的底物范围，为异羟肟酸的有效分子间烯基化奠定了基础。详细的力学研究表明，通过羧酸盐的协助以及随后的迁移性炔烃插入，还原消除和分子内氧化加成，可在动力学上实现C–H的金属化。

  DOI：

  10.1021/jo501884v

文献信息

• <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。
• Direct Access to Cobaltacycles via C–H Activation: <i>N</i>-Chloroamide-Enabled Room-Temperature Synthesis of Heterocycles
  作者：Xiaolong Yu、Kehao Chen、Shan Guo、Pengfei Shi、Chao Song、Jin Zhu

  DOI：10.1021/acs.orglett.7b02632

  日期：2017.10.6

  Cobaltacycle synthesis via C–H activation has been achieved for the first time, providing key mechanistic insight into cobalt catalytic chemistry. N-Chloroamides are used as a directing synthon for cobalt-catalyzed room-temperature C–H activation and construction of heterocycles. Alkynes as coupling partners allow convenient access to isoquinolones, a class of synthetically and pharmaceutically important

  首次通过C–H活化合成钴环化合物，提供了对钴催化化学的关键机理的见解。N-氯酰胺用作钴催化的室温C–H活化和杂环构建的直接合成子。炔烃作为偶联伙伴可以方便地获得异喹诺酮，这是一类重要的合成和药学上重要的化合物。广泛的底物范围使得可以将各种各样的取代模式结合到杂环支架中。
• Ruthenium-Catalyzed C–H/N–O Bond Functionalization: Green Isoquinolone Syntheses in Water
  作者：Lutz Ackermann、Sabine Fenner

  DOI：10.1021/ol202861k

  日期：2011.12.16

  Ruthenium-catalyzed isoquinolone syntheses with ample scope were accomplished through carboxylate assistance in environmentally benign water as a reaction medium. The high chemoselectivity of the ruthenium(II) carboxylate complex also set the stage for the direct use of free hydroxamic acids for annulations of alkynes.