6913-92-4, 1-Benzyl-3-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
Nitrone 12 (149 mg, 0.72 mmol) and N-benzyl-3-pyrroline 2 (170 muL, 0.89 mmol) were dissolved in toluene (2 mL) containing a few drops of CH2Cl2 for solubilization. Cycloaddition was completed after stirring for 1 h at 80 C under micro-wave irradiation. The solvent was evaporated under reduced pressure and purification of the residue by silica gel column chromatography (mobile phase: 1/9 EtOAc/toluene) afforded cycloadduct (+-)-16 (180 mg, 68% yield). Colourless oil; Rf = 0.6 (EtOAc/toluene 1/4). 1H NMR (500 MHz, 50 C, CDCl3) delta 7.25-7.45 (m, 10H, H-Ar), 4.62 (dd, 1H, J = 4.9 Hz, J = 7.6 Hz, H-4), 4.22 (d, 1H, 2J = 13.7 Hz, ONCH2Ph), 4.12 (dq, 2H, 3J8,9 = 7.1 Hz, J = 1.6 Hz, H-8), 4.05 (d, 1H, 2J = 13.7 Hz, ONCH2Ph), 3.68 (d, 1H, 2J = 13.2 Hz, NCH2Ph), 3.61 (d, 1H, 2J = 13.2 Hz, NCH2Ph), 3.39 (d, 1H, 3J = 7.0 Hz, H-6), 3.28 (q, 1H, 3J = 7.0 Hz, H-3), 3.00 (d, 1H, 3J = 11 Hz, H-5′), 2.95 (d, 1H, 3J = 9.6 Hz, H-2′), 2.32 (br s, 1H, H-2), 2.21 (br s, 1H, H-5), 1.24 (t, 3H, 3J = 7.1 Hz, H-9). 13C NMR (126 MHz, 50 C, CDCl3) delta 170.28 (C=O), 138.64, 136.93, 129.50, 128.76, 128.44, 128.30, 127.47, 127.23 (12C-ar), 81.05 (C-4), 73.09 (C-6), 61.24 (C-8), 60.92 (C-10), 59.06 (C-11), 58.88 (C-5), 56.94 (C-2), 52.23 (C-3), 14.23 (C-9). 2D NOE correlations were confirmed by 1D NOE experiments with selective irradiations (H-3, H-4, or H-6), showing signals enhancements as follows: H-3 irradiation: enhancements of H-2: 3.7%, H-2′: 1.7%, H-4: 5.2%; irradiation of H-4: enhancements of H-3: 3.9%, H-5: 2.9%, H-5′: 2.0%, H-6: 1.0%; irradiation of H-6: enhancements of H-2: 0.9%, H-2′: 3.9%, H-4: 1.4%. HRMS-ESI, positive mode: m/z calcd for C22H27N2O3 [M+H]+: 367.2016; found: 367.2009.
6913-92-4 1-Benzyl-3-pyrroline 561506, apyrrolines compound, is more and more widely used in various.
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