一种多取代呋喃化合物的制备方法_2

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122 .5, 120. 7, 113. 8, 77. 4, 77. 0, 76. 6, 55. 19, 3. 21, 3. 55, 23. 0.1 R(neat, cm :) : 3060 (w), 29 58 (w), 1667 (s), 1560 (m), 1519 (s), 1299 (m), 1255 (s), 1176 (m), 1031 (m), 951 (m), 835 (w ),764(w), 699(w). MS(EI, 70eV) :m/z = 356 (M+). HRMS (ESI) :m/z: [M+H] (C20H2102S2), Cal cd. :357. 0983. Found:357. 0977.
[0041] 实施例6所得产品的结构、核磁、红外、质谱、高分辨质谱数据如下:
[0042] :H NMR(300MHz, CDC13) 8 7. 34 - 7. 15 (m, 9H), 6. 83 (s, 1H), 2. 97 (t, J = 7. 0Hz, 2H), 2. 71 (dt, J = 8. 1, 6. 9Hz, 2H), 2. 18 (s, 3H), 2. 02 - 1. 92 (m, 2H), 1. 36 (t, J = 8.1Hz,1H).13CNMR(75MHz,CDC13)5 152.1,144.6,137.5,133.0,130.6,130.4,129.0,128. 5, 127. 1, 126. 8, 125. 7, 124. 3, 118. 3, 34. 0, 33. 5, 22. 9, 20. 1. IR(neat, cm :) : 3058 (w), 2925 (w),2856(w), 1673 (m), 1603 (s), 1502 (s), 1446 (m), 1265 (s), 1131(m), 1026 (m), 952 (s), 78 2 (m), 697 (m), 664 (w), 584 (w). MS (El, 70eV) : m/z = 340 (M+). HRMS (ESI) :m/z: [M+H] (C20H21 0S2),Calcd. :341. 1034. Found:341. 1031.
[0043] 实施例7所得产品的结构、核磁、红外、质谱、高分辨质谱数据如下:
[0044] :H NMR(300MHz, CDC13) 8 7. 52 - 7. 28(m, 7H), 7. 17(d, J = 8. 4Hz, 2H) , 6. 67 (s, 1H) , 2. 99 (t, J = 6. 9Hz, 2H) , 2. 9 1 (s, 1H), 2. 74 (dd, J = 14. 9, 6. 9Hz, 2H), 2. 07 - 1. 93 (m, 2H), 1. 38 (t, J = 8. 1Hz, 1H), 1. 26 (d, J = 6. 9Hz, 6H). 13C NMR(75MHz, CDC13) S 151. 4, 148. 6, 143. 9, 133. 7, 128. 6, 128. 5, 128. 1,127. 2, 126. 4, 126. 1 ,123. 2, 120. 7, 34. 1, 33. 8, 33. 5, 23. 8, 22. 9. IR (neat, cm :) : 3059 (w), 2924 (w), 2826 (w), 16 70 (m), 1600 (m), 1509 (s), 1440 (m), 1265 (s), 1194 (m), 1133 (m), 1047 (m), 958 (s), 789 (m), 7 47 (m), 693 (m), 651 (w), 572 (w). MS (El, 70eV) :m/z = 368 (M+). HRMS (ESI) :m/z: [M+H] (C22H25 0S2),Calcd. :369. 1347. Found:369. 1349.
[0045] 实施例8所得产品的结构、核磁、红外、质谱、高分辨质谱数据如下:
[0046] 4 匪R (300MHz, CDC13) S 7. 46 - 7. 22 (m, 5H),6. 74 - 6. 52 (m, 3H),6. 36 (s, 1H ),3.65(s,6H),2.97(t,J = 7.0Hz,2H),2.71 (dd,J = 14.8, 7. 2Hz,2H),1.97 (p,J = 6. 9Hz,2H),1. 36 (t,J = 8. 2Hz,1H) ? 13C NMR (75MHz,CDC13) S 160. 5, 150. 8, 144. 3, 133. 5 ,132. 0, 128. 7, 128. 5, 127. 4, 124. 3, 120. 6, 103. 8, 100. 6, 55. 2, 34. 0, 33. 5, 22. 9. IR(ne at, cm :) : 3114 (w), 3002 (w), 2962 (m), 2937 (m), 2840 (m), 1666 (s), 1550 (m), 1506 (s), 14 54 (m), 1344 (m), 1202 (s), 1155 (m), 1065 (m), 1040 (m), 948 (m), 834 (s), 766 (m), 699 (m). MS(EI, 70eV) :m/z = 386 (M+). HRMS (ESI) :m/z : [M+H] (C21H2303S2), Calcd. : 387. 1089. Found: 387. 1092.
[0047] 实施例9所得产品的结构、核磁、红外、质谱、高分辨质谱数据如下:
[0048] :H NMR(300MHz, CDC13) 8 7. 49 - 7. 40 (m, 2H), 7. 38 - 7. 29 (m, 5H), 7. 26 - 7. 20 (m, 2H), 6. 63 (s, 1H), 2. 97 (t, J = 7. 0Hz, 2H), 2. 71 (dt, J = 8. 0, 6. 9Hz, 2H), 1. 97 (p, J =6. 9Hz, 2H),1. 36 (t, J = 8. 1Hz, 1H) ? 13C NMR (75MHz, CDC13) S 150. 0, 144. 9, 133. 5, 133. 3, 129. 0, 128. 8, 128. 5, 127. 8, 127. 6, 127. 2, 124. 4, 120. 8, 120. 4, 34. 0, 33. 5, 22. 9. IR(neat, cm :) : 3058 (w), 2924 (m), 2853 (w), 1676 (s), 1587 (s), 1499 (s), 1445 (m), 1263 (s), 1136 (m), 1093 (m), 1012(m),951(m),833(s),766(m),699(m),516(w).MS(EI,70eV) :m/z = 360 (M+). HRMS(ESI) :m/z: [M+H] (C19H18C10S2), Calcd. :361. 0488. Found: 361. 0484.
[0049] 实施例10所得产品的结构、核磁、红外、质谱、高分辨质谱数据如下:
[0050] 4 NMR(300MHz, CDC13) S 8. 10 (d, J = 1. 0Hz, 1H),7. 87 - 7. 69 (m, 3H),7. 59 (dd, J =8. 6, 1. 8Hz, 1H), 7. 42 (dddd, J = 12. 5, 7. 2, 5. 8, 3. 5Hz, 7H), 6. 73 (s, 1H), 3. 04 (t, J =7. 0Hz, 2H), 2. 86 - 2. 68(m, 2H), 2. 03(p, J = 6. 9Hz, 2H), L 40 (t, J = 8. 1Hz, 1H). 13C 匪R(75MHz, CDC13) S 151. 2, 144. 7, 133. 5, 133. 2, 132. 7, 128. 7, 128. 6, 128. 2, 128. 0, 12 7. 9, 127. 6, 127. 4, 126. 3, 126. 3, 125. 2, 124. 3, 124. 1, 120. 7, 34. 1, 33. 6, 23. 0.1 R(neat ,cm :) : 3054 (w), 2930 (m), 2937 (m), 1667 (s), 1628 (m), 1502 (s), 1445 (m), 1358 (m), 126 4(s), 1129 (m), 1047 (m), 947 (m), 896 (s), 763 (m), 700 (m), 574 (w). MS (El, 70eV) :m/z = 376(M+). HRMS(ESI) :m/z: [M+H] (C23H210S2), Calcd. :377. 1034. Found: 377. 1030.
[0051] 实施例11所得产品的结构、核磁、红外、质谱、高分辨质谱数据如下:
[0052] :H NMR(300MHz, CDC1 3) 8
7.51 -7.42(m,2H),7.42-7. 29 (m, 4H), 6. 66 (s, 1H), 6. 55 (dd, J = 3. 4, 0. 7Hz, 1H), 6. 44 - 6. 37 (m, 1H), 2. 96 (t, J =7.0Hz, 2H), 2.69 (dd,J = 15. 0,7.0Hz, 2H), 1.96 (p,J = 7.0Hz, 2H), 1.36 (t,J = 8.1Hz,1H).13CNMR(75MHz,CDC13)S145.6,144.8,143.4,142.1,132.5,128.5,128.4,127. 5, 123. 9, 120. 2, 111. 2, 107. 8, 34. 1, 33. 5, 22. 9. IR(neat, cm :) : 3117 (w), 2927 (m), 2858 (m) ,1668(s), 1601(w), 1561(w), 1504(s), 1496(m), 1462(s), 1383 (w), 1260 (m),1137 (m),1013 (m), 948(m), 763(s), 699(m), 594(w). MS(El, 70eV):m/z = 316(M+). HRMS(ESI):m/z:[M+H] (C17H1702S 2),Calcd. : 317. 0670. Found: 317. 0674.
[0053] 实施例12所得产品的结构、核磁、红外、质谱、高分辨质谱数据如下:
[0054] :H NMR(300MHz, CDC13) 8 7. 45 - 7. 26 (m, 9H), 6. 63 (s, 1H), 2. 98 (t, J = 7. 0Hz, 2H), 2. 71 (dd, J = 14. 9, 7. OHz, 2H), 1. 98 (p, J = 7. OHz, 2H), 1. 36 (t, J = 8. 1Hz, 1H) ? 13C NMR (75MHz, CDC13) S 150. 0, 145. 0, 133. 3, 131. 6, 129. 4, 128. 8, 128. 5, 127 .6, 124. 5, 121. 8, 120. 6, 34. 0, 33. 5, 23. 0.1 R(neat, cm :) : 3051 (w), 2927 (m), 2853 (w), 1 675 (s), 1588 (s), 1500 (s), 1446 (m), 1264 (s), 1137(m), 1072 (m), 1009 (m), 951 (m), 830 (m ),701(s),576(w).MS(EI,70eV) :m/z = 404 (M+). HRMS (ESI) :m/z: [M+H] (C19H18BrOS2), Cal cd. :404. 9982. Found:404. 9979.
[0055] 实施例13所得产品的结构、核磁、红外、质谱、高分辨质谱数据如下:
[0056] 4 MMR(300MHz,CDCl3)S7.33-7.17(m,5H),7.01(d,J = 8.6Hz,lH),6.82-6. 73 (m, 1H), 6. 65 (d, J = 8. 7Hz, 1H), 3. 87 (dd, J = 4. 2, 3. 6Hz, 6H), 3. 65 (s, 3H), 2. 9 6(t, J = 6. 9Hz, 2H), 2. 71 (dd, J = 14. 6, 7. 4Hz, 2H), 2. 02 - 1. 90 (m, 2H), 1. 36 (t, J = 8.1Hz,1H).13CNMR(75MHz,CDC13)S154.9,152.3,149.2,144.4,142.3,133.4,128.4,127. 3, 126. 7, 125. 8, 124. 4, 118. 8, 117. 8, 107. 0, 60. 9, 55. 96, 34. 1,33. 5, 23. 0? IR(neat,cm 丄): 3120 (w),3012(w),2969(m),2847(m),1665(s),1543(m),1500 (s),1454 (m),1397 (m),1344 ( m), 1219 (s), 1145 (m), 1049 (m), 943 (m), 833 (s), 767 (m), 699 (m), 530 (w). MS (El, 70eV) :m/z =416 (M+). HRMS (ESI) :m/z: [M+H] (C22H2504S2), Calcd. :417. 1194. Found: 417. 1190.
[0057] 实施例14所得产品的结构、核磁、红外、质谱、高分辨质谱数据如下:
[0058] :H NMR (300MHz, CDC13) 8 7. 46 - 7. 14 (m, 8H), 6. 96 - 6. 83 (m, 1H), 6. 62 (d, J =1. 2Hz, 1H), 2. 98(t, J
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