Caffeic acid phenethyl ester (CAPE): Synthesis and X-ray crystallographic analysis

被引：39
|
作者：
Son, S
Lobkowsky, EB
Lewis, BA [1 ]
机构：
[1] Cornell Univ, Div Nutr Sci, Ithaca, NY 14853 USA
[2] Cornell Univ, Dept Food Sci, Ithaca, NY 14853 USA
[3] Cornell Univ, Dept Chem & Biol Chem, Ithaca, NY 14853 USA
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 2001年 / 49卷 / 02期
关键词：
caffeic acid phenethyl ester; alkylation reaction; X-ray diffraction; hydroxycinnamic acid derivative; phenolic compound;
D O I：
10.1248/cpb.49.236
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The structure of caffeic acid phenethyl ester [2-propenoic acid, 3-(3, 4-dihydroxyphenyl)-, 2-phenethyl ester] (I), C17H16O4.1/2C(6)H(6), synthesized by base-catalyzed alkylation of caffeic acid salt with beta -bromoethylbenzene in HMPA (hexamethylphosphoramide) and recrystallized from benzene, was confirmed by single crystal X-ray diffraction. The crystals are triclinic, space group P (1) over bar, Z=2, unit cell dimension a=5.8129 (9) Angstrom, b=11.122 (2) Angstrom, c= 13. 226 (2) Angstrom, alpha =97.080 (3)degrees, beta =101.467 (3)degrees, gamma =95.405 (3)degrees, V=825.4 (2) Angstrom (3), D-calc=1.301 g/cm(3), F(000)=342. The packing of the molecule is stabilized by intermolecular O1H . . .O-4 (2.69 Angstrom) and O-1. . . HO2 (2.82 Angstrom) hydrogen bonds.
引用
收藏
页码：236 / 238
页数：3
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