3475-21-6Relevant articles and documents
Pentacyclic Cage Formation in the Intramolecular Addition of Tricyclic Nitrones
Mackay, Donald,Watson, Kenneth N.
, p. 777 (1982)
Despite their anti-configurations three tricyclic nitrones, on heating in toluene, undergo high-yield intramolecular addition to give the corresponding pentacyclic cages; a co-product from heating two of the nitrones in tetrachloroethylene is the pyridyl ketone.
Enhancement of the electroluminescence properties of iridium-complexes by decorating the ligand with hole-transporting carbazole dendrons
Thathong, Yuranan,Chasing, Pongsakorn,Manyum, Thanaporn,Namuangruk, Supawadee,Saengsuwan, Sayant,Sudyoasuk, Taweesak,Promarak, Vinich
, p. 7694 - 7704 (2021)
Iridium complexes are particularly essential and have been intensively utilized as emissive phosphorescence emitters for efficient phosphorescent electroluminescent (EL) devices. In order to improve the EL performance, a series of new iridium complexes decorated with carbazole dendrons in a non-conjugated fashion using an ether linkage were designed and synthesized. The iridium(iii) bis(4-methyl-2-phenylpyridinato-N,C2′)picolinate substituted with a hexyl chain (IrG0), N-hexyl carbazole (IrG1), N-hexyl-N′-9,3′:6′,N′′-tercarbazole (IrG2) and N-hexyl-6′,6′′′-di(carbazol-N-yl)-N′′,3′:N′,3′′:6′′,N′′′:3′′′,N′′′′-quinquecarbazole (IrG3) was designed to afford improved hole-transporting properties without affecting the iridium core's photophysical and electronic properties. The synthesized iridium complexes exhibited intense yellowish-green photoluminescence (PL) emissions at 542-561 nm in the film state. The hole-transporting capability of the complexes was found to be improved when carbazole dendrons were incorporated in the ligand and increased as the generation of the substituent carbazole dendrons increased in the order of IrG0 IrG1 IrG2 IrG3. In particular, the use of IrG3, showing the highest hole mobility, in an organic light-emitting diode (OLED) device resulted in a strong and stable green emission peaking at 532 nm (color coordinates CIE x, y of (0.36, 0.56)) with a brightness of 16?170 cd m-2, the maximum luminous efficiency of 13.59 cd A-1 and a maximum EQE of 4.36%. This journal is
Discovery of 9,10-dihydrophenanthrene derivatives as SARS-CoV-2 3CLpro inhibitors for treating COVID-19
Zhang, Jian-Wei,Xiong, Yuan,Wang, Feng,Zhang, Fu-Mao,Yang, Xiaodi,Lin, Guo-Qiang,Tian, Ping,Ge, Guangbo,Gao, Dingding
, (2021/12/09)
The epidemic coronavirus disease 2019 (COVID-19) caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has now spread worldwide and efficacious therapeutics are urgently needed. 3-Chymotrypsin-like cysteine protease (3CLpro) is an indispensable protein in viral replication and represents an attractive drug target for fighting COVID-19. Herein, we report the discovery of 9,10-dihydrophenanthrene derivatives as non-peptidomimetic and non-covalent inhibitors of the SARS-CoV-2 3CLpro. The structure-activity relationships of 9,10-dihydrophenanthrenes as SARS-CoV-2 3CLpro inhibitors have carefully been investigated and discussed in this study. Among all tested 9,10-dihydrophenanthrene derivatives, C1 and C2 display the most potent SARS-CoV-2 3CLpro inhibition activity, with IC50 values of 1.55 ± 0.21 μM and 1.81 ± 0.17 μM, respectively. Further enzyme kinetics assays show that these two compounds dose-dependently inhibit SARS-CoV-2 3CLpro via a mixed-inhibition manner. Molecular docking simulations reveal the binding modes of C1 in the dimer interface and substrate-binding pocket of the target. In addition, C1 shows outstanding metabolic stability in the gastrointestinal tract, human plasma, and human liver microsome, suggesting that this agent has the potential to be developed as an orally administrated SARS-CoV-2 3CLpro inhibitor.
Water-Accelerated Nickel-Catalyzed α-Crotylation of Simple Ketones with 1,3-Butadiene under pH and Redox-Neutral Conditions
Chen, Tiantian,Dong, Guangbin,Xing, Dong,Yang, Haijian,Yang, Yang
, p. 4238 - 4243 (2020/05/05)
We report a nickel/NHC-catalyzed branched-selective α-crotylation of simple ketones using 1,3-butadiene as the alkylation agent. This reaction is regioselective and operated under pH and redox-neutral conditions. Water was used as the sole additive, which significantly accelerates the transformation.
gamma-alkenyl ketone and preparation method thereof
-
Paragraph 0232-0236, (2020/02/29)
The invention discloses a gamma-alkenyl ketone preparation method, wherein the target product can be obtained at high yield and high regioselectivity by using acetophenone and 1,3-butadiene as raw materials in the presence of an organic solvent, a catalyst, an additive and a ligand. According to the invention, the method has advantages of high atom economy, high regioselectivity, high yield and the like, can achieve the efficient conversion from a cheap basic organic chemical product 1,3-butadiene to high-added-value gamma-alkenyl ketone, and uses the cheap catalyst, so that the reaction conditions are neutral and mild, and the experimental operation is safe and simple; and the synthesized gamma-alkenyl ketone is a useful synthetic intermediate, can be subjected to a series of conversionsto obtain a series of drug molecule precursors or key intermediates, and has wide application prospect.
N-heterocyclic carbene enabled rhodium-catalyzed ortho C(sp2)-H borylation at room temperature
Zhong, Lei,Zong, Zhi-Hong,Wang, Xi-Cun
supporting information, p. 2547 - 2552 (2019/03/27)
We report a rhodium-catalyzed ortho C(sp2)-H borylation of 2-phenylpyridines using commercially available N-heterocyclic carbenes (NHCs) as ligand and pinacolatodiboron (B2pin2) as borylating reagent. The reaction could take place at room temperature, tolerating a wide range of functionalities and affording ortho borylated products in moderate to excellent yields. The current method is also applicable to gram-scale reaction with reduced catalyst loading.
Visible Light Induced Rhodium(I)-Catalyzed C?H Borylation
Thongpaen, Jompol,Manguin, Romane,Dorcet, Vincent,Vives, Thomas,Duhayon, Carine,Mauduit, Marc,Baslé, Olivier
supporting information, p. 15244 - 15248 (2019/10/22)
An efficient visible light induced rhodium(I)-catalyzed regioselective borylation of aromatic C?H bonds is reported. The photocatalytic system is based on a single NHC?RhI complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature. The chelating nature of the NHC-carboxylate ligand was critical to ensure the stability of the RhI complex and to provide excellent photocatalytic activities. Experimental mechanistic studies evidenced a photooxidative ortho C?H bond addition upon irradiation with blue LEDs, leading to a cyclometalated RhIII-hydride intermediate.
C–H Bond Activation by a Ruthenium(II) β-Diketonate Complex: A Mechanistic Study
Bri?, Anamarija,Turel, Iztok,Roithová, Jana
supporting information, p. 6107 - 6113 (2018/09/14)
Ruthenium(II)-catalysed C–H bond activation of arenes containing a functional directing group depends on the ligand coordinated to ruthenium(II). In this study, 2-phenylpyridine C–H activation catalysed by a “piano-stool“ ruthenium(II) complex containing a fluorinated β-diketonate ligand was examined by ESI-MS in combination with CID experiments. [Ru(β-diketonate)(CTPhPy)Cl]+ was identified as an active intermediate, and its collisional activation leads to C–H activation. CID analysis indicates proton transfer from the phenylpyridine to the chlorine anion, showing HCl elimination, while the β-diketonate ligand is retained in the complex together with the activated phenylpyridine. Furthermore, DFT calculations were performed for the neutral analogue [Ru(β-diketonate)(PhPy)Cl] to identify all ruthenium intermediates along the C–H activation reaction pathway. The results suggest that the most stable structure of [Ru(β-diketonate)(PhPy)Cl] has pre-activated 2-phenylpyridine with a partly developed Ru–H bond. Further, we show that K2CO3 is not directly involved in the C–H activation step and it serves in the reaction as a base.
Recyclable alkylated fac-Ir(ppy)3 complex as a visible-light photoredox catalyst for the synthesis of 3-trifluoromethylated and 3-difluoroacetylated coumarins
Zhang, Xiaodan,Li, Yaming,Hao, Xinyu,Jin, Kun,Zhang, Rong,Duan, Chunying
supporting information, p. 7358 - 7363 (2018/11/23)
A recyclable fac-tris(heptadecanyl-2-phenylpyridine) iridium [fac-Ir(hdppy)3] photocatalyst was synthesized. The hexane-phase-selective solubility of fac-Ir(hdppy)3 in a thermomorphic multicomponent solvent (TMS) allowed its easy recycling by automatic liquid/liquid separation at room temperature. The excellent catalytic and recoverable activities of fac-Ir(hdppy)3 were demonstrated via trifuoromethylation and difluoroacetylation reactions of phenyl 3-phenylpropiolate under visible-light irradiation in a TMS system.
Directed: Ortho C-H borylation catalyzed using Cp?Rh(iii)-NHC complexes
Thongpaen, Jompol,Schmid, Thibault E.,Toupet, Loic,Dorcet, Vincent,Mauduit, Marc,Baslé, Olivier
supporting information, p. 8202 - 8205 (2018/07/29)
Cp?Rh(NHC) complexes with bulky chiral bidentate NHC-carboxylate ligands were efficiently synthesized and fully characterized including solid-state structures. These unprecedented rhodium(iii) complexes demonstrated high selectivity in pyridine-directed ortho-C-H borylation of arenes under mild conditions.
