612-96-4 Usage
Description
2-Phenylquinoline is the major quinoline alkaloid of Galipea iongiflora, a Bolivian plant used as treatment for cutaneous leishmaniasis. It possesses antinociceptive properties and has been evaluated for its efficacy against different models of pain in mice.
Used in Pharmaceutical Industry:
2-Phenylquinoline is used as a potential therapeutic agent for the treatment of cutaneous leishmaniasis, a parasitic disease caused by Leishmania species.
Used in Pain Management:
2-Phenylquinoline is used as an antinociceptive agent for the management of pain in various models, demonstrating its potential as a pain-relieving compound.
Used in Drug Design and Development:
2-Phenylquinoline is used as a reference compound in quantitative structure-activity relationship (QSAR) analyses for the development of estrogen receptor β-selective ligands, contributing to the advancement of drug design and discovery.
Preparation
Synthesis of 2-phenylquinoline: Quinoline (1.0 g, 7.742 mmol) and phenyl lithium (2.30 mL, 2 M, 23.22 mmol) were reacted according to general procedure. Purification of the residue by silica gel column chromatography (EtOAc:MeOH:Et3N; 10-30:1:1 or PhMe:MeOH:Et3N; 10:1:1) gave 2-phenylquinoline (0.66 g, 42%) as an orange solid.Aniline (0.140 g, 1.50 mmol) and cinnamaldehyde (0.132 g, 1.00 mmol) were dissolved in toluene in a reaction vial equipped with a magnetic stirrer bar, followed by the addition of K10 (0.50 g). The reaction mixture was heated at a temperature of 110 ?C for 3 hours. After completion of the reaction, the crude product was purified by column chromatography over silica gel eluting with a mixture of Hexane : Ethyl acetate (20:1) to produce 2-Phenylquinoline as a yellow solid (0.044 g, 21%); (m.p. 82-84 ?C) (lit. 84-85 °C); Rf 0.67 (20:1 hexane:ethyl acetate);1H NMR (400 MHz, CDCl3) δH 7.46-7.51 (1H, m, H-4’), 7.53-7.56 (3H, m, H-6, 3’, 5’), 7.73- 7.77 (1H, m, H-7), 7.85 (1H, d, J = 8.31 Hz, H-5), 7.88-7.91 (1H, d, J = 8.31 Hz, H-3), 8.18- 8.27 (4H, m, H-4, 8, 2’, 6’)13C NMR(400 MHz, CDCl3) δC 119.2 (C-3), 126.7 (C-6), 127.2 (C-4a), 127.5 (C-2’, 6’), 127.9 (C-5), 128.4 (C-3’, 5’), 128.7 (C-4’), 128.9 (C-7, 8), 129.8 (C-4), 130.3 (C-1’), 137.9 (C-8a), 157.2 (C-2)
Synthesis Reference(s)
Synthetic Communications, 23, p. 1959, 1993 DOI: 10.1080/00397919308009854Chemical and Pharmaceutical Bulletin, 26, p. 3485, 1978 DOI: 10.1248/cpb.26.3485Journal of the American Chemical Society, 71, p. 2327, 1949 DOI: 10.1021/ja01175a017
Check Digit Verification of cas no
The CAS Registry Mumber 612-96-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 2 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 612-96:
(5*6)+(4*1)+(3*2)+(2*9)+(1*6)=64
64 % 10 = 4
So 612-96-4 is a valid CAS Registry Number.
InChI:InChI=1/C15H11N/c1-2-6-12(7-3-1)15-11-10-13-8-4-5-9-14(13)16-15/h1-11H
612-96-4Relevant articles and documents
Substrate-Tuned Domino Annulation for Selective Synthesis of Poly-substituted Benzo[ f]imidazo[2,1- a][2,7]naphthyridines and 3-Azaheterocyclic Substituted 2-Arylquinolines
Ying, Zhimin,Cen, Jie,Luo, Feng,Wu, You,Liu, Shuangrong,Chen, Wenteng,Shao, Jiaan,Yu, Yongping
, p. 4747 - 4755 (2021)
A domino annulation/oxidation of heterocyclic ketene aminals (HKAs) and 2-aminochalcones has been developed for the selective synthesis of poly-substituted benzo[f]imidazo[2,1-a][2,7]naphthyridines and 3-azaheterocyclic substituted 2-arylquinolines. These reactions proceed well under mild conditions without any additives. Plausible mechanisms for such a polycyclic ring system assembly were also proposed. Moreover, benzo[f]imidazo[2,1-a][2,7]naphthyridine 3g displayed a fluorescence effect, demonstrating the potential applications in organic optical materials.
Furfuryl vinyl ethers in [4+2]-cycloaddition reactions
Oparina,Vysotskaya,Stepanov,Ushakov,Apartsin,Gusarova,Trofimov
, (2017)
For the first time [4+2]-cycloaddition reactions were carried out between furfuryl vinyl ethers and typical dienophiles and heterodienes proceeding in uncatalyzed conditions and resulting in previously unknown heterocyclic systems containing either free v
Dehydrogenation of N-Heterocyclic Compounds Using H2O2 and Mediated by Polar Solvents
Llopis, Natalia,Gisbert, Patricia,Baeza, Alejandro,Correa-Campillo, Jara
, p. 1205 - 1210 (2022/02/25)
The oxidative dehydrogenation of N-heterocyclic compounds by using H2O2 as oxidant in combination with polar solvents such as 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) and H2O is described. Among these two solvents, the best yields for the heteroaromatic compounds were generally achieved in HFIP. However, it is remarkable, that the use of a non toxic solvent such as H2O gave such good yields. Furthermore, the procedure was implemented in larger-scale and HFIP was distilled from the reaction mixture and reused (up to 5 cycles) without a significant detriment in the reaction outcome. (Figure presented.).
Manganese(III) Acetate Catalyzed Aerobic Dehydrogenation of Tertiary Indolines, Tetrahydroquinolines and an N-Unsubstituted Indoline
Niu, Xiaokang,Yang, Lei
supporting information, p. 4209 - 4215 (2021/08/06)
A Mn(OAc)3 ? 2H2O-catalyzed aerobic dehydrogenation of five and six-membered N-heterocycles for the synthesis of N-heteroarenes is reported. Of note, this protocol can be applied to the dehydrogenation of tertiary indolines with various electron-deficient N-substituents. Preliminary mechanistic investigations support that a single-electron transfer pathway might be involved. (Figure presented.).