Journal of Molecular Structure 967 (2010) 25–33
Journal of Molecular Structure
Synthesis and structural study on heterocyclic compounds
7-decanoyloxy-3-(40-substitutedphenyl)-4H-1-benzopyran-4-ones: Crystal
structure of 7-decanoyloxy-3-(40-methylphenyl)-4H-1-benzopyran-4-one
a
b
c
Guan-Yeow Yeap a, , Wan-Sinn Yam , Paulina Dominiak , Masato M. Ito
*
a Liquid Crystal Research Laboraotry, School of Chemical Sciences, Universiti Sains Malaysia, 11800 Minden, Penang, Malaysia
b Department of Chemistry, Warsaw University, Al.Zwirki I Wigury, 101, 02-089, Warsaw, Poland
c Department of Environmental Engineering for Symbiosis, Faculty of Engineering, Soka University, Hachioji, Tokyo 192-8577, Japan
a r t i c l e i n f o
a b s t r a c t
Six new isoflavone-based esters, 7-decanoyloxy-3-(40-substitutedphenyl)-4H-1-benzopyran-4-ones,
derived from 1,3-benzenediol (resorcinol) and different para substituted phenylacetic acids have been
synthesized and characterized. The molecular structures of the title compounds were elucidated with
the employment of physical measurements and spectroscopic techniques (FTIR, 1D and 2D NMR). The
conformation of 7-decanoyloxy-3-(40-methylphenyl)-4H-1-benzopyran-4-one was determined by single
crystal X-ray diffraction analysis of which the title compound crystallized into triclinic lattice with P-1
space group. Crystal structure of the title compound also revealed that the two phenyl rings of the central
moiety were planar whilst the heterocyclic ring was found to pucker slightly from the mean plane.
Ó 2010 Published by Elsevier B.V.
Article history:
Received 6 August 2009
Received in revised form 8 December 2009
Accepted 12 December 2009
Available online 23 December 2009
Keywords:
7-Decanoyloxy-3-(40-substitutedphenyl)-
4H-1-benzopyran-4-ones
Single crystal X-ray diffraction analysis
Triclinic
Mean plane
FTIR
1D and 2D NMR
1. Introduction
ies of the title compounds in respective liquid and solid states. The
molecular structures and characteristics of the title compounds
Isoflavones are water-soluble chemicals found in many plants.
They comprise a class of often naturally occurring organic com-
pounds related to the flavonoids [1]. Although isoflavones are not
essential nutrients, their therapeutic and medicinal values in
reducing the incidence of several diseases and improving other
measures linked to cardiovascular risk were well documented
[2,3]. Some isoflavones and isoflavone-rich foods possess anti-can-
cer properties, including certain types of breast and prostate cancer
[4]. Another interesting feature of isoflavone derivatives is their
ability to form rod-like, calamitic liquid crystals of which many
of the compounds were polymorphic, exhibiting wide thermomor-
phic ranges [5,6]. Hence, we are prompted to explore the new iso-
flavone derivatives which may possess significant use particularly
in materials science.
will also be discussed. The synthetic routes toward the formation
of the intermediates and title compounds are shown in Fig. 1.
The molecular structures of all title compounds were elucidated
by spectroscopic techniques: fourier transformed infrared (FTIR)
and high resolution nuclear magnetic resonance, NMR (1H and
13C, homonuclear 1H–1H COSY, heteronuclear 1H–13C HMQC and
1H and 13C HMBC correlation studies). A crystal structure of 7-
decanoyloxy-40-methyl-isoflavone is further confirmed by single
crystal X-ray diffraction analysis.
2. Experimental
Resorcinol (Aldrich), methanesulfonyl chloride, boron trifluor-
ide (Merck), decanoyl chloride (Acros), phenylacetic acid, and its
p-substituted analogues (p-fluoro-, p-chloro-, p-bromo-, p-nitro-,
p-tolyl-, and p-methoxyphenylacetic acids) (TCI, Japan) were used
without further purification.
In this paper, we report a new series of isoflavone derivatives, 7-
decanoyloxy-3-(40-substitutedphenyl)-4H-1-benzopyran-4-ones
wherein the decanoyloxy chain was attached to the central moiety
via an ester linkage. This paper focuses on the conformational stud-
2.1. Syntheses of 1-(2, 4-dihydroxyphenyl)-2-(40-substitutedphenyl)-
ethanones, 1–6
* Corresponding author. Fax: +60 4 6574854.
A mixture containing 5 g of the appropriate 4-substituted phen-
Yeap).
ylacetic acid and 1.2 equiv of resorcinol in 40 ml BF3ꢀEt2O was
0022-2860/$ - see front matter Ó 2010 Published by Elsevier B.V.