Диссертация (1150039), страница 19
Текст из файла (страница 19)
Реакционную смесь разделяли с помощью колоночной хроматографии (SiO2,элюент гексан/ацетон 20:1→2:1): в результате был выделен изохинолиндион 29а(126 мг, 71% : смесь двух диастереомеров 7 : 1).121(3S*,4aR*,8aS*)-8-Гидрокси-2-(4-метоксифенил)-8a-метил-3-фенил-3,4,4a,5тетрагидроизохинолин-1,6(2H,8aH)-дион(29а).Бесцветноекристаллическоевещество, т.пл.
191-193 °С; ИК спектр (пленка, ν/см-1): 3463, 2944, 2836, 1708, 1630,1608, 1557, 1508, 1456, 1425; 1411, 1243, 1216; Спектр 1Н ЯМР (400 МГц, CDCl3), δ,м.д.: 12.22 (с, 1H, OH), 6.98-7.35 (м, 5H, Ph), 6.85 (д, J = 8.9 Гц, 2H, PMP), 6.73 (д, J= 8.9 Гц, 2H, PMP), 5.48 (с, 1H, CH=), 4.90 (дд, J = 10.9, 6.7 Гц, 1H, C3H), 3.70 (s, 3H,OMe), 2.88-2.98 (м 1H, CH), 2.05-2.55 (м, 4H, 2CH2), 1.91 (с, 3H, OMe); Спектр 13СЯМР (101 МГц, CDCl3), δ, м.д.: 196.1, 180.3, 176.6 (2CO+HO-C=C), 158.6, 139.4,131.7, 128.9, 128.5, 128.4, 127.3, 114.3, 105.3 (2Ar+C=), 65.9, 55.3, 41.8, 38.7, 35.8,33.7, 21.4 (OMe+С-четв.+2СH+2CH2+Me); HRMS (ESI) вычислено для C23H23NO4[M+H]+ 378.1700, найдено 378.1696.122СПИСОК СОКРАЩЕНИЙ И УСЛОВНЫХ ОБОЗНАЧЕНИЙAc2Oуксусный ангидридBINOL1,1'-Би-2-нафтолDBU1,8-Диазабициклоундес-7-енPTSAП-ТолуолсульфокислотаTsтозил (пара-толуолсульфонил)HRMSмасс-спектрометрия высокого разрешенияТСХтонкослойная хроматографияMCRмультикомпонентная реакцияTBSтрет-бутилдиметилсилилEWGэлектрон-акцепторная группа123СПИСОК ЛИТЕРАТУРЫ[1] Salzmann, T.
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