6913-92-4,6913-92-4, 1-Benzyl-3-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
Cyanonitrone 13 (550 mg, 3.44 mmol) and N-benzyl-3-pyrroline2 (1.3 mL, 6.83 mmol) were dissolved in toluene (4 mL) and themediumwas stirred for 2 h at 80 C under micro-waves irradiation.The solvent was removed under reduced pressure before purificationby silica gel column chromatography (eluent: EtOAc/toluene 1/10). This allowed the separation of a minor more mobileregioisomer (60 mg, 6%) from the main racemic cycloadduct expected(¡À)-17 (500 mg, 45%). Compound (¡À)-17: Yellowish oil.Rf 0.4 (1:4 EtOAc/toluene). 1H NMR (500 MHz, 80 C, toluene-d8)d 7.4e7.0 (m, 10H, HeAr), 4.28 (ddd, 1H, J 3.4 Hz, J 6.0 Hz,J 7.5 Hz, H-4), 4.15 (d, 1H, J 13.4 Hz, H-8), 3.80 (d, 1H, J 13.4 Hz,H-8), 3.29 (d, 1H, J 13.1 Hz, H-9), 3.23 (d, 1H, J 13.1 Hz, H-9), 3.07(d, 1H, J 3.6 Hz, H-6), 2.79 (ddd, 1H, J 4.0 Hz, J 7.8 Hz,J 11.6 Hz, H-3), 2.48 (dd, 1H, J 3.1 Hz, J 10.1 Hz, H-50), 2.22 (br s,1H, H-5), 2.17 (br m, 1H, H-20), 2.09 (br m, 1H, H-2). 1D NOE experimentswith selective irradiations (H-3, H-4, or H-6), showedsignals enhancements as follows: H-3 irradiation: enhancements ofH-2: 2.5%, H-2?: 1.9%, H-4: 2%, H-6: 1.1%; irradiation of H-4: enhancementsof H-3: 2.1%, H-5: 1.9%, H-5?: 1.4%; irradiation of H-6:enhancements of H-2: 2%, H-2?: 1.8%. 13C NMR (126 MHz, 80 C,toluene-d8): d 139.8 (Caear), 137.2 (Ca?-ar), 130.2, 129.5, 129.4,129.3, 128.6, 128.1 (10C-ar), 116.9 (C-7), 81.9 (C-4), 60.0 (C-9), 59.9(C-6), 59.8, 59.7 (C-5, C-8), 57.5 (C-2), 53.6 (C-3). HRMS-ESI, positivemode: m/z calcd for C20H22N3O [MH]: 320.1757; found:320.1767.Compound (¡À)-18: yellow clear oil. Rf 0.6 (1/4 EtOAc/toluene).1H NMR (500 MHz, toluene-d8) d 7.5e7.0 (m, 10H, HeAr), 4.40 (dd,1H, J 4.7 Hz, J 7.7 Hz, H-4), 3.71 (d, 1H, J 8.1 Hz, H-6), 3.39 (s,2H, H-9), 3.20 (d, 1H, J 17.2 Hz, H-7), 3.01 (d, 1H, J 10.8 Hz, H-50),2.77 (d, 1H, J 17.2 Hz, H-7), 2.71 (d, 1H, J 9.7 Hz, H-20), 2.64 (app.q, 1H, J 7.3 Hz, H-3), 1.73 (m, 2H, H-2, H-5). 13C NMR (126 MHz,toluene-d8) d 140.02 (Caear), 138.41 (Ca?-ar), 129.84,129.35, 129.35,129.31, 128.93, 128.02 (10C-ar), 115.00 (C-8), 82.19 (C-4), 76.02 (C-6), 59.54 (C-9), 59.28 (C-5), 58.04 (C-3), 56.60 (C-2), 42.16 (C-7). 2DNMR (HMBC) showed correlations between H-6 and aromaticcarbons, as well as correlations between methylene H-7 and C-8 inthe nitrile group. 1D NOE experiments with selective irradiations(H-3, H-4, or H-6), showed signals enhancements as follows: H-3irradiation: enhancements of H-2: 4.6%, H-4: 4.2%, H-6: 1.1%, HeAr:3.5%; irradiation of H-4: enhancements of H-3: 3.8%, H-5: 4.1%, H-5?: 1.2%; irradiation of H-6: enhancements of H-2?: 2.9%, H-5?: 0.3%,HeAr: 5.4%. HRMS-ESI, positive mode: m/z calcd for C20H22N3O[MH]: 320.1757; found: 320.1750.
6913-92-4 1-Benzyl-3-pyrroline 561506, apyrrolines compound, is more and more widely used in various fields.
Reference£º
Article; Cecioni, Samy; Aouadi, Kaiss; Guiard, Julie; Parrot, Sandrine; Strazielle, Nathalie; Blondel, Sandrine; Ghersi-Egea, Jean-Francois; Chapelle, Christian; Denoroy, Luc; Praly, Jean-Pierre; European Journal of Medicinal Chemistry; vol. 98; (2015); p. 237 – 249;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem