7-(trifluoromethyl)-3,4-diphenylisoquinolin-1(2H)-one | 1225462-94-1

• 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: 7-(trifluoromethyl)-3,4-diphenylisoquinolin-1(2H)-one
• 英文别名: 3,4-diphenyl-7-(trifluoromethyl)-2H-isoquinolin-1-one
• CAS: 1225462-94-1
• 化学式: C₂₂H₁₄F₃NO
• 分子量: 365.354
• InChiKey: WPHKELKZWOEEJL-UHFFFAOYSA-N

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：

  7-(trifluoromethyl)-3,4-diphenylisoquinolin-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-3'-(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：

  3-(三氟甲基)苯甲酰氯 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 cesium acetate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 20.0h， 生成 7-(trifluoromethyl)-3,4-diphenylisoquinolin-1(2H)-one
  参考文献：
  名称：

  对铑 (III) 催化的异喹诺酮合成的校正：N-O 键作为 C-N 键形成和催化剂周转率的处理

  摘要：

  DOI：

  10.1021/ja3096625

文献信息

• Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N−O Bond as a Handle for C−N Bond Formation and Catalyst Turnover
  作者：Nicolas Guimond、Christina Gouliaras、Keith Fagnou

  DOI：10.1021/ja102571b

  日期：2010.5.26

  to access the isoquinolone motif via cross-coupling/cyclization of benzhydroxamic acid with alkynes is described. The reaction features a regioselective cleavage of a C-H bond on the benzhydroxamic acid coupling partner as well as a regioselective alkyne insertion. Mechanistic studies point out the important involvement of a N-O bond as a tool for C-N bond formation and catalyst turnover.

  描述了通过苯异羟肟酸与炔烃的交叉偶联/环化获得异喹诺酮基序的无外部氧化剂过程。该反应的特点是区域选择性裂解苯异羟肟酸偶联物上的 CH 键以及区域选择性炔烃插入。机理研究指出 NO 键作为 CN 键形成和催化剂周转的工具的重要参与。
• 一种合成异吲哚并[2,1-b]异喹啉-5(7H)-酮类化合物的方法
  申请人：广州大学

  公开号：CN113666925B

  公开（公告）日：2022-05-17

  本发明属于有机合成、金属催化领域，公开了一种由NH异喹啉酮与烯丙基醇制备多取代异吲哚并[2,1‑b]异喹啉‑5(7H)‑酮类化合物的方法。本发明的技术方案要点为：以五甲基环戊二烯基铑配合物为催化剂，3‑苯基异喹啉‑1‑(2H)酮和烯丙基醇为原料，在有机溶剂中，于130℃下反应6h，反应结束后冷却反应液，减压除去有机溶剂，粗产物通过二氧化硅柱纯化，石油醚/乙酸乙酯洗脱，得到纯的多取代异吲哚并[2,1‑b]异喹啉‑5(7H)‑酮类化合物。本发明为这类化合物增加了一种新颖的合成途径，该合成方法具有反应操作简便、原料易制备、底物普适性广、中等到良好的产率等优点。
• Rhodium(<scp>iii</scp>)-catalyzed oxidative annulation of isoquinolones with allyl alcohols: synthesis of isoindolo[2,1-<i>b</i>]isoquinolin-5(7<i>H</i>)-ones
  作者：Jinyuan Jiang、Jidan Liu、Zhenke Yang、Jieying Zheng、Xin Tian、Liyao Zheng、Zhao-Qing Liu

  DOI：10.1039/d1ob02305e

  日期：——

  An efficient rhodium(III)-catalyzed direct C–H oxidative annulation of isoquinolones with allyl alcohols as C1 synthons has been successfully developed. This protocol enables the straightforward synthesis of structurally diverse isoindolo[2,1-b]isoquinolin-5(7H)-ones with high atom economy, tolerates a broad spectrum of functionalities, and is applicable to one-pot operation from readily available

  已经成功开发了一种高效的铑（III）催化的异喹诺酮类与烯丙醇作为 C1 合成子的直接 C-H 氧化环化。该协议能够直接合成结构多样的 isoindolo [2,1- b ]isoquinolin-5(7 H )-ones，具有高原子经济性，耐受广泛的功能，适用于从现成的N的一锅操作-甲氧基苯甲酰胺。
• Dehydrative C–H/N–OH Functionalizations in H₂O by Ruthenium(II) Catalysis: Subtle Effect of Carboxylate Ligands and Mechanistic Insight
  作者：Fanzhi Yang、Lutz Ackermann

  DOI：10.1021/jo501884v

  日期：2014.12.19

  A ruthenium(II) complex derived from the electron-deficient aromatic carboxylic acid 3-(F3C)C6H4CO2H proved to be a highly efficient catalyst for dehydrative alkyne annulation by NH-free hydroxamic acids in water. The C–H/N–OH functionalization occurred with excellent positional selectivity as well as ample substrate scope, setting the stage for effective intermolecular alkenylations of hydroxamic

  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。
• Oxidative Coupling of NH Isoquinolones with Olefins Catalyzed by Rh(III)
  作者：Fen Wang、Guoyong Song、Zhengyin Du、Xingwei Li

  DOI：10.1021/jo2002209

  日期：2011.4.15

  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.