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有机化学
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有机化学 ›› 2003, Vol. 23 ›› Issue (2): 182-186. 上一篇    下一篇

研究论文

三种O－异戊烯基苯丙素类天然产物的首次合成

王倩;何侃侃;侯自杰   

  1. 兰州大学有机化学研究所,兰州(730000)
  • 发布日期:2003-02-25

First synthesis of three naturally occurring O-prenylated phenylpropanoids

Wang Qian;He Kankan;Hou Zijie   

  1. Institute of Organic Chemistry,National Laboratory of Applied Organic Chemistry,Lanzhou University,Lanzhou(730000)
  • Published:2003-02-25

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以香草醛为起始原料，经O－异戊烯基化、Witting反应、水解、还原、氧化等 反应步骤，首次合成了三种苯丙素天然产物boropinalA（1），boropinalC（2） boropinicAcid（3）,有化合物结构均由核磁共振氢谱，质谱及红外光谱确证，用 X射线衍射法测定了3的晶体及分子结构。

关键词: 香草醛;核磁共振谱法;红外分光光度法;X射线衍射分析;晶体结构, 分子结构

The first synthesis of three naturally occurring phenylpropanoids, boropinol A (1), boropinal C (2) and boropinic acid (3), is described. The reaction of vaniline (4) with prenyl bromide in DMF gave the 0- prenylated product 5 in 84% yield. Condensation of 5 with Ph-3P= CHCO- 2Et in DME produced ester 6 in 52% yield. Hydrolysis of 6 with aqueous KOH followed by acidification gave boropinic acid (3) in 91% yield. Compound 3 was obtained as a nice crystal instead of a liquid as that reported in literature. The structure of 3 was confirmed by X-ray crystal structural analysis in addition to its solution spectrum data. Reduction of 3 by LiAlHj in dry diethyl ether gave a mixture of compound 1 and 7. This mixture was not seperated and was oxidized by K- 2Cr-2O-7 in DMSO to give compound 2 in 61% yield. Pure boropinol A (1) was obtained in 70% yield by the reduction of 2 with NaBHi in CH-3OH.

Key words: vanillin, 1HNMR, IR, XRD, CRYSTAL STRUCTURE, MOLECULAR STRUCTURE

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