编辑: f19970615123fa | 2019-07-09 |
0 °C and the resulting mixture was stirred at room temperature for
1 h. After the crude material was poured into ice water, organic layer was extracted with EtOAc, washed with water and brine, and dried over MgSO4. After removing the solvent in vacuo, the crude material was purified by silica gel column chromatography (hexane:EtOAc = 80:20) to afford the titled compound (4.12 g, 7.27 mmol, 97%) as white solid. M.p.: 117.5C118.8 °C.
1 H NMR (600 MHz, CDCl3): δ 0.89 (t, J = 7.2 Hz, 6H, CH3), 1.26C1.41 (m, 28H, (CH2)7), 1.72 (quin, J = 7.2 Hz, 4H, ArCH2CH2), 2.77 (t, J = 7.2 Hz, 4H, ArCH2), 5.51 (s, 2H, OH), 7.24 (d, J = 8.4 Hz, 2H, ArH), 7.36 (s, 2H, ArH), 7.54 (s, 2H, ArH), 7.73 (d, J = 8.4 Hz, 2H, ArH), 7.80 (s, 2H, ArH).
13 C NMR (150 MHz, CDCl3): δ 14.3, 22.9, 29.51, 29.53, 29.7, 29.78, 29.80, 31.5, 32.1, 36.4, 111.0, 124.8, 125.0, 126.1, 127.7, 127.8, 130.8, 135.2, 142.0, 151.3. TOF HRMS (APCI): Calcd for C40H55O2 [M+H]567.4202, found 567.4199. Anal. Calcd for C42H54O2: C, 84.75;
H, 9.60. Found: C, 84.81;
H, 9.34. 7,7'
-Didecyl-2,2'
-binaphthalene-3,3'
-diol (for synthesis of C10CDNFCVV) White solid. Yield: 97%. M.p.: 105.4C106.8 °C.
1 H NMR (400 MHz, CDCl3): δ 0.88 (t, J = 6.4 Hz, 6H, CH3), 1.26C1.35 (m, 28H, (CH2)7), 1.72 (quin, J = 7.6 Hz, 4H, ArCH2CH2), 2.76 (t, J = 7.6 Hz, 4H, ArCH2), 5.63 (s, 2H, OH), 7.34 (d, J = 8.4 Hz, 2H, ArH), 7.39 (s, 2H, ArH), 7.58 (s, 2H, ArH), 7.69 (d, J = 8.4 Hz, 2H, ArH), 7.79 (s, 2H, OMe MeO C10H21 C10H21 OH HO C10H21 C10H21 BBr3 (2.2 eq) DCM
0 °C to rt,
1 h 97% OH HO H21C10 C10H21 BBr3 (2.2 eq) CH2Cl2
0 °C to rt,
1 h OMe MeO H21C10 C10H21 97% S6 ArH).
13 C NMR (100 MHz, CDCl3): δ 14.3, 22.8, 29.5, 29.70, 29.76, 29.78 (two carbons), 31.6, 32.1, 36.1, 111.4, 125.9, 126.3, 126.4, 128.9, 129.5, 130.6, 133.4, 139.1, 150.7. TOF HRMS (APCI): Calcd for C40H55O2 [M+H]567.4202, found 567.4213. General procedure of synthesis of C10CDNFCV derivatives: 3,........