多酚黄酮类化合物及其制备方法和应用_2

文档序号:9299582阅读:来源:国知局
. 6 (C-IO),123. 4 (C-l '), 132.4(C-2',6' ),116.4(C-3',5' ),159.9(C-4' ),100.5(C-1" ),80.3(C-2"), 79.2(C-3 " ),72.4(C-4 " ),76.0(C-5 " ),64.3(C-6 " ),100.3(C-1 "'), 72.7(C-2" ' ),72.6(C-3" ' ),74.4(C-4" ' ),70.3(C-5" ' ),17.9(C-6"'), 127.5(C-1" " ),131.5(C-2" ",6" " ),117.2(C-3" ",5" " ),161.6(C-4""), 146.9(C-7" " ),114.9(C-8" " ),169.1(C-9" " )·
[0055] 化合物4 :黄色粉末(甲醇)。盐酸-镁粉、Moiish反应为阳性。1H-Nmr^oomhz, DMS0-d 6) δ h:6. 16(1H,d,J = 2. OHz,H-6),6. 36(1H,d,J = 2. OHz,H-8),7. 96(2H,d,J = 8.8Hz,H-2,,6,),6.87(2H,d,J = 8.8Hz,H-3,,5,),5.72(lH,d,J = 8.0Hz,H-l"), 7.40(2H,d,J = 8.5Hz,H-2",,6",),6.79(2H,d,J = 8.5Hz,H-3",,5",), 7. 35(1H,d,J = 15. 8Hz,H-7",),6. 15 (1H,d,J = 15. 8Hz,H_8 ",),7. 55 (2H,d,J = 8.6Hz,H-2" ",6" " ),6.79(2H,d,J = 8.6Hz,H-3" ",5" " ),7.61(lH,d,J=15.8Hz, H-7" " ),6.43(lH,d,J=15.8Hz,H-8" " ).13C-NMR(150MHz,DMS0-d6)Sc:156.5(C-2), 133. 2 (C-3),177. 2 (C-4),161. 2 (C-5),98. 8 (C-6),164. 3 (C-7),93. 8 (C-8),156. 4 (C-9), 103.9(C-10),120.0(C-1' ),130.9(C-2',6' ),115.2(C-3',5' ),160.2(C-4'), 100.3(C-1" ),73.9(C-2" ),73.9(C-3" ),70.2(C-4" ),74.4(C-5" ),62.8(C-6"), 125.0(C-1" ' ),130.3(C-2" ',6" ' ),115.9(C-3" ',5" ' ),159.9(C-4"'), 144.8(C-7" ' ),113.7(C-8" ' ),166.2(C-9" ' ),125.2(C-1" " ),130.4(C-2"", 6" " ),115.9(C-3" ",5" " ),160.1(C-4" " ),145.2(C-7" " ),114.3(C-8""), 165. 9(C-9"").
[0056] 化合物5:黄色粉末(甲醇)。盐酸-镁粉、Moiish反应为阳性。1H-Nmrgoomh z, DMS0-d6) δ h:6. 18(lH,d,J = I. 5Hz,H-6),6. 37(lH,d,J = I. 5Hz,H-8),7. 19(2H,s,H-2,, 6,),5.46(lH,d,J = 7.5Hz,H-l" ),4.2(lH,d,J=12Hz,Ha-6" ),4·3(1Η,(Μ,Λ=12·0, 5.0Hz,^-6;/ ) ,6. 88(2H, r ,H-6^ r ). 13C-NMR(100MHz, DMS〇-d6) δ c: 155. 9 (C-2, C-9),133. 5 (C-3),177. 7 (C-4),161. I (C-5),98. I (C-6),164. 0 (C-7),93. 9 (C-8), 103. 2 (010),121.1(01' ),108.9(02',C-6',C-2" ',C-6" ' ),145.0(C-3', C-5',C-3" ',C-5" ' ),136. l(C-4' ),103.9(C-1" ),73. l(C-2" ),70.0(C-4"), 76. l(C-5 " ),64.0(C-6 " ),120.8(C-1 " ' ),74. 2 (C_3 " ),138. I (C_4 "'), 165.9(0-7^ r ).
[0057] 化合物6 :黄色粉末(甲醇)。盐酸-镁粉、Moiish反应为阳性。1H-Nmr^oomhz, C5D5N) δ h:6. 69(1H,d,J = 2. 2Hz,H-6),6. 74(1H,d,J = 2. 2Hz,H-8),8. 26(1H,d, J = 2.2Hz,H-2 ' ),7.23(lH,d,J = 8.2Hz,H-5 ' ),3.81(3H,s,0CH3),7.38(1H, (Μ,Λ=8·2,2·2Ηζ,Η-6,),5.23(lH,d,J = 7.5Hz,H-l" ),7.71(2H,s,H-2",, H-6 " ' ) · 13C-NMR(150MHz,C5D5N) δ c:157. 8 (C-2),135. I (C-3),178. 6(C-4,), 162. 8 (C-5),100. 0 (C-6),166. 0 (C-7),94. 8 (C-8),157. 7 (C-9),105. 3 (C-IO),121. 3 (C-I), 114. 6 (C-2r ),151. 4 (C-3r ),148. I (C-4r ),116. 3 (C-5r ),123. KC-Br ), 56. 4 (OCH3), 104.7(C-1" ),76.0(C-2" ),78.4(C-3" ),71.2(C-4" ),76.2(C-5" ),64.2(C-6"), 121.0(C-1" ' ),110.3(C-2" ',C-6" ' ),147.2(C-3" ',C-5" ' ),140.6(C-4"'), 167.0(0-7^ r ).
[0058] 化合物7:黄色粉末(甲醇)。盐酸-镁粉、Moiish反应为阳性。1H-Nmrgoomh z, CD3OD) δ h:6. 56(1H,d,J = 2. 3Hz,H-6),6. 87(1H,d,J = 2. 3Hz,H-8),7. 64(1H,d,J = 2.1Hz,H-2,),6.80(lH,m,J = 8.4Hz,H-5,),7·58(1Η,(Μ,Λ8·4,2·1Ηz,Η-6,), 5.86(lH,d,J = 7.9Hz,H-l" ),7·63(2Η,8,Η-2"' /6"' ). 13C-NMR(100MHz,CD30D)Sc: 158. 2 (C-2),135. I (C-3),178. 4 (C-4),163. I (C-5),99. 2 (C-6),166. I (C-7),94. 5 (C-8), 158. 8(C-9),105. 6(C-IO),123.0 (C-l' ),117. 2(C-2 ' ),145. 7(C-3' ),149. 7(C-4 '), 115.9(C-5' ),123.6(C-6' ),100.0(C-1" ),76.6(C-2" ),76.1(C-3" ),71.1(C-4"), 77.6(C-5" ),61.3(C-6" ),121.2(C-1" ' ),111.0(C-2" ',6" ' ),146.3(C-3"', 5" ' ),140.2(C-4" ' ),169.1(C-7" ' )·
[0059] 化合物8 :黄色粉末(甲醇)。盐酸-镁粉、Moiish反应为阳性。1H-Nmrgoomhz, CD3OD) δ h:6. 56(1H,d,J = 2. 3Hz,H-6),6. 87(1H,d,J = 2. 3Hz,H-8),8. 55(2H,d,J = 8.2Hz,H-2,,6,),7.66(2H,d,J = 8.2Hz,H-3,,5,),5.86(lH,d,J = 7.9Hz,H-l"), 7.63(2H,s,H-2" ' /6" ' ). 13C-NMR(100MHz,CD30D)Sc:158.2(C-2),133.1(C-3), 178. 4 (C-4),163. I (C-5),99. 2 (C-6),166. I (C-7),94. 5 (C-8),158. 8 (C-9),105. 6 (C-IO), 123.0(C-1' ),133.0(C-2',6'),117.2(C-3',5'),162.7(C-4' ),100.0(C-1"), 76.6(C-2" ),76.1(C-3" ),71.1(C-4" ),77.6(C-5" ),61.3(C-6" ),121.2(C-1"'), 111.0(C-2" ',6" ' ),146.3(C-3" ',5" ' ),140.2(C-4" ' ),169.1(C-7" ' )·
[0060] 化合物9 :黄色粉末(甲醇)。盐酸-镁粉、Moiish反应为阳性。1H-Nmrgoomhz, CD3OD) δ h:6. 13(1H,d,J = 2. 1Hz,H-6),6. 30(1H,d,J = 2. 1Hz,H-8),7. 20(2H,s,H-2', 6,),5.76(lH,d,J = 7.9Hz,H-l" ),7.12(2H,s,H-2" ',6" ' ).13C-NMR(100MHz, CD3OD) δ c: 158. 2 (C-2),133. I (C-3),178. 9 (C-4),I δ 3. I (C-5),99. 9 (C-6),166. 3 (C-7), 94. 6 (C-8),158. 4 (C-9),105. 7 (C-IO),122. 2 (CM' ),109.9(02',6' ),146.4 (C-3', 5 ' ),137.9(C-4 ' ),100.7(C-1 " ),76.2(C-2 " ),76.6(C-3 " ),71.5(C-4 "), 78.7(C-5" ),62.5(C-6" ),121.4(C-1" ' ),110.6(C-2" ',6" ' ),146.5(C-3"', 5" ' ),140.0(C-4" ' ),168.1(C-7" ' )·
[0061] 化合物io :黄色粉末(甲醇)。盐酸-镁粉、Moiish反应为阳性。1H-Nmr^oomhz, C5D5N) δ h:6. 65(1H,d,J = 2. 2Hz,H-6),6. 67(1H,d,J = 2. 2Hz,H-8),8. 83(1H,d,J = 2. 2Hz,H-2 ' ),7. 21 (1H,d,J = 8. 2Hz,H-5 ' ),3. 81 (3H,s,0(?),7. 80 (1H,dd,J = 8·2,2·2Ηζ,Η-6' ),5.80(lH,d,J = 8.0Hz,H-l" ),7.41(2H,d,J = 8.8Hz,H-2"', H-6",),7.12(2H,d,J = 8.8Hz,H-3",,H-5",),7.70(lH,d,J=16.0Hz,H-7",), 6. 35(1H,d,J= 16.0Hz,H-8" ')· 13C-NMR(150MHz,C5D5N) δ c:157.6(C-2),135. I (C-3), 178. 5 (C-4),162. 7 (C-5),99. 9 (C-6),166. 0 (C-7),94. 7 (C-8),157. 6 (C-9),105. 2 (C-IO), 121.2(C-1 r ),114.6 (C-2 r ),151. 3 (C-3 r ),148.0 (C-4 r ),116. 3 (C-5 r ), 123.1(C-6' ),56.4(0CH3),104.7(C-1" ),76.0(C-2" ),78.3(C-3" ),71.2(C-4"), 76.2(C-5" ),64.2(C-6" ),125.2(C-1" ' ),131.0(C-2" ',C-6" ' ),116.1(C-3"', C-5" ' ),160.3(C-4" ' ),144.5(C-7" ' ),112.9(C-8" ' ),167.1(C-9" ' )·
[0062] 化合物11 :黄色粉末(甲醇)。盐酸-镁粉、Mo I i sh反应为阳性。1H-NMR (400MHz, CD30D)SH:6.29(lH,br s H-6),6.57(lH,br s,H-8),7.11(lH,d,J = 2.1Hz,H-2,), 6. 23(1H,m,J = 8. 4Hz,H-5,),7. 12 (1H,dd,J = 8. 4, 2. 1Hz,H_6,),5. 46 (1H,d,J = 7.5Hz,H-l" ),5.12(lH,br s,H-l" ' ),7.60(2H,s,H-2" ',6" ' ).13C-NMR(100MHz, CD3OD) δ c: 158. I (C-2),133. 9 (C-3),178. 7 (C-4),163. 4 (C-5),100.1 (C-6),166. 2 (C-7), 95. I (C-8),158. 5 (C-9),106. 9 (C-10),122. 9 (C-l ' ),116. 9 (C-2 ' ),145. I (C-3 '), 149.5(C-4' ),116.2(C-5' ),100.1(C-1" ),80.1(C-2" ),79.0(C-3" ),71.8(C-4"), 76.9(C-5" ),64.2(C-6" ),103.3(C-1" ' ),72.1(C-2" ' ),72.2(C-3"'), 74.8(C-
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