6913-92-4, 1-Benzyl-3-pyrroline is a pyrrolines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,6913-92-4
A solution of nitrone 11 (300 mg, 2.29 mmol) and N-benzyl-3-pyrroline 2 (0.8 mL, 4.20 mmol) in toluene (3 mL) was stirred for 1 h at 80 C under micro-wave irradiation. TLC (1:3 EtOAc/petroleum ether) showed complete conversion of the nitrone into a major product, and unidentified polar byproducts. The solvent was evaporated and the residue was subjected to silica gel column chromatography (mobile phase: 1:4 EtOAc/toluene) to afford cycloadduct (+-)-14 (390 mg, 58%). Colourless oil. Rf = 0.4 (1:4 EtOAc/toluene). 1H NMR (500 MHz, CDCl3) delta 7.35-7.20 (m, 5H, H-Ar), 4.60 (dd, 1H, J = 4.9 Hz, J = 7.4 Hz, H-4), 4.20 (q, 2H, J = 7.1 Hz, H-8), 3.70 (d, 1H, J = 13.2 Hz, NCH2Ph), 3.58 (d, 1H, J = 13.2 Hz, NCH2Ph), 3.25 (q, 1H, J = 7.1 Hz, H-3), 3.17 (br s, 1H, H-6), 3.00 (d, 1H, J = 11 Hz, H-5′), 2.94 (d, 1H, J = 9.8 Hz, H-2′), 2.78 (s, 3H, NCH3), 2.28 (br t, 1H, J = 7.6 Hz, H-2), 2.19 (br d, 1H, J = 6.6 Hz, H-5), 1.27 (t, 3H, J = 7.1 Hz, H-9). 1D NOE experiments with selective irradiations (H-3, H-4, or H-6), showed signals enhancements as follows: H-3 irradiation: enhancements of H-2: 4%, H-2′: 1.8%, H-4: 4%; irradiation of H-4: enhancements of H-3: 3.5%, H-5: 3.7%, H-5′: 1.9%; irradiation of H-6: enhancements of H-2: 1.3%, H-2′: 2.7%. 13C NMR (126 MHz, CDCl3) delta 170.03 (CO), 138.58 (C-ar), 128.73, 128.41, 127.17 (5CH-ar), 81.03 (C-4), 75.48 (C-6), 61.26 (C-8), 59.08 (C-11), 58.77 (C-5), 56.79 (C-2), 52.54 (C-3), 43.85 (NCH3), 14.24 (C-9). HRMS-ESI, positive mode: m/z calcd for C16H23N2O3 [M+H]+: 291.1703; found: 291.1702.
As the paragraph descriping shows that 6913-92-4 is playing an increasingly important role.
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