北京大学药学院高等波谱解析前言和香豆素类化合物实用教案

1、天然化合物结构解析(ji x)(ji x)的一般程序 第1页/共23页第一页，共24页。可能存在自旋方向 预期图谱 峰强度比 第2页/共23页第二页，共24页。7.85(1H, d, J=9.5Hz, H-4) 6.18(1H, d, J=9.5Hz, H-3) 7.45(1H, d, J=8.3Hz, H-5) 第3页/共23页第三页，共24页。 (1H, d, J=9.5Hz, H-4) (1H, d, J=8.3Hz, H-5) (1H, d, J=9.5Hz, H-3) (1H, dd, J=2.2, 8.3Hz, H-6) (1H, d, J=2.2Hz, H-8) The 1H N

2、MR Spectrum of Umbelliferone第4页/共23页第四页，共24页。728a45634a8The 13C NMR Spectrum of Umbelliferone155.4111.3102.1161.2113.0129.6144.4111.3160.31OOHO第5页/共23页第五页，共24页。7.921HdJ=9.5HzH-4 7.471HsH-5 6.781HsH-8 6.211HdJ=9.5HzH-3 4.711HtJ=8.8HzH-23.192HdJ=8.8HzH-31.163HsH-51.143HsH-68a4a87654321OOOHO23456The 1H

3、 NMR Spectrum of Nodakenetin第6页/共23页第六页，共24页。The 13C NMR Spectrum of Nodakenetin728a4654a3824356OOOHO160.4111.1144.5112.0155.0123.8125.4163.296.728.790.969.924.825.8第7页/共23页第七页，共24页。7.941HdJ=9.5HzH-46.231HdJ=9.5HzH-37.491HsH-56.231HsH-84.911HtJ=8.8HzH-24.891HdJ=7.3HzH-14.401HdJ=7.3HzH-1第8页/共23页第八页，共

4、24页。7.941HdJ=9.5HzH-4 7.491HsH-5 6.811HsH-8 6.231HdJ=9.5HzH-3 4.911HtJ=8.8HzH-24.891HdJ=7.3HzH-14.401HdJ=8.0HzH-6b3.681HddJ=8.0, 12.5HzH-6a3.282HdJ=8.8HzH-31.323HsH-51.193HsH-6The 1H NMR Spectrum of Nodakenin65432123456784a8aOOHHOHOOHOOOO2345615243第9页/共23页第九页，共24页。72 8a46534a816423543562The 13C NMR

5、Spectrum of Nodakenin97.261.276.970.376.673.5OOHHOHOOHOOOO155.0111.296.8123.8125.4144.6112.2160.489.729.177.023.220.6163.0第10页/共23页第十页，共24页。The 1H NMR Spectrum of Forbesoside第11页/共23页第十一页，共24页。4.972HtJ=8.8HzH-34.621HdJ=7.8HzG-14.491HddJ=11.6HzG-6b4.351HddJ=11.6HzG-6aOH3.80OMe3.611HdddJ=2.3, 8.0, 9.0

6、HzG-5G-3G-4G-227.601HdJ=9.3HzH-47.461HdJ=16.1HzH-87.171HsH-56.891HdJ=2.0HzH-26.791HddJ=2.0, 8.1HzH-66.681HdJ=8.1HzH-56.521HsH-86.171HdJ=16.1HzH-76.091HdJ=9.3HzH-31654328a4a8765432123456OOOOOHHOHOOOOHOOMe789第12页/共23页第十二页，共24页。The 1H NMR Spectrum of Tetraacetyl6-O-(trans-Feruloyl)Nodakenin1654328a4a87

7、65432109111213OOOOOAcAcOAcOOCH2OMeAcOOO789612345第13页/共23页第十三页，共24页。The 1H NMR Spectrum of Tetraacetyl6-O-(trans-Feruloyl)nodakenin第14页/共23页第十四页，共24页。7.601HdJ=16.0HzH-77.521HdJ=9.5HzH-4 7.121HsH-5 7.03 (2H, d, J=3.2Hz, H-5, 6)7.02 (1H, s, 2)6.651HsH-8 6.311HdJ=16.0HzH-86.161HdJ=9.5HzH-3 5.241HtJ=9.4H

8、zH-35.061HtJ=9.4HzH-44.941HddJ=9.4HzH-24.801HtJ=8.8HzH-10 4.831HdJ=8.1HzH-14.351HddJ=2.7, 12.0HzH-6b 4.281HddJ=6.1, 12.0HzH-6a 3.821HdddJ=2.9, 6.1, 9.4HzH-53.853HsOMe 3.172HdJ=8.8HzH-9 2.333HsAr-OAc(-Me) 2.053HsGlc-OAc(-Me) 1.993HsGlc-OAc(-Me) 1.863HsGlc-OAc(-Me) 1.353Hs131.263Hs121654328a4a87654321

9、09111213OOOOOAcAcOAcOOCH2OMeAcOOO789612345The 1H NMR Spectrum of Tetraacetyl6-O-(trans-Feruloyl)nodakenin第15页/共23页第十五页，共24页。The 13C NMR Spectrum of Tetraacetyl6-O-(trans-Feruloyl)nodakeninCOOCH3COOCH39728a347465156824a381101135246OMe91312第16页/共23页第十六页，共24页。香豆素类化合物的NMR特征(tzhng)第17页/共23页第十七页，共24页。OO+-

10、C3、C6、C8-H在较高场C4、C5、C7-H在较低场核磁共振波谱规律1H-NMR受内酯羰基吸电子(dinz)共轭效应的影响第18页/共23页第十八页，共24页。OOHH43OOHRO37C-7有氧取代(qdi)，第19页/共23页第十九页，共24页。OORH45C-5有基团(j tun)取代，H-4 -0.3 ppm，在之间第20页/共23页第二十页，共24页。OOOHH2323OOOHH呋喃香豆素如果(rgu)呋喃环上没有取代 H-2,H-2 7.34-7.80 线型，角型第21页/共23页第二十一页，共24页。OO23456788a4a160.4116.4143.6118.8128.1124.4131.8116.4有OR取代(qdi) 直接相连的碳 +30ppm邻碳 13ppm对碳 8ppm13C-NMR第22页/共23页第二十二页，共24页。感谢您的观看(gunkn)！第23页/共23页第二十三页，共24页。NoImage内容(nirng)总结天然化合物结构解析的一般程序。第