1,2,3-Trimethoxy-4-[(E)-2-phenylvinyl]benzene and (E,E)-1,4-bis(2,3,4-trimethoxyphenyl)buta-1,3-diene

被引:2
作者
Santos, Jana Sopkova-de Oliveira [1 ]
Bazin, Marc-Antoine [1 ]
Lohier, Jean-Francois [2 ]
El Kihel, Laila [1 ]
Rault, Sylvain [1 ]
机构
[1] Univ Caen, CNRS, CERMN, INC3M,EA 3915,FR 3038, F-14032 Caen, France
[2] Univ Caen, ENSICAEN, CNRS, Lab Chim Mol & Thioorgan,UMR 6507, F-14050 Caen, France
来源
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY | 2009年 / 65卷
关键词
TRANS-STILBENE; 1,2-DIARYLETHENES; FLUORESCENCE; RESVERATROL;
D O I
10.1107/S0108270109019702
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The stilbene derivative 1,2,3-trimethoxy-4-[(E)-2-phenylvinyl]benzene, C17H18O3, (I), and its homocoupling co-product (E, E)-1,4-bis(2,3,4-trimethoxyphenyl) buta-1,3-diene, C22H26O6, (II), both have double bonds in trans conformations in their conjugated linkages. In the structure of stilbene (I), the aromatic rings deviate significantly from coplanarity, in contrast with coproduct (II), the core of which is rigorously planar. The deviation in stilbene (I) seems to be driven by intermolecular electrostatic interactions. Diene (II) sits on a crystallographic inversion centre, which bisects the conjugated linkage.
引用
收藏
页码:O311 / O313
页数:3
相关论文
共 16 条
  • [1] [Anonymous], APEX2 SAINT
  • [2] Therapeutic potential of resveratrol:: the in vivo evidence
    Baur, Joseph A.
    Sinclair, David A.
    [J]. NATURE REVIEWS DRUG DISCOVERY, 2006, 5 (06) : 493 - 506
  • [3] Original one-pot microwave-promoted Hunsdiecker-Suzuki strategy:: straightforward access to trans-1,2-diarylethenes from cinnamic acids
    Bazin, Marc-Antoine
    El Kihel, Laiela
    Lancelot, Jean-Charles
    Rault, Sylvain
    [J]. TETRAHEDRON LETTERS, 2007, 48 (25) : 4347 - 4351
  • [4] ABSORPTION AND FLUORESCENCE SPECTRA OF CRYSTALLINE TRANS-STILBENE
    CHAUDHURI, MK
    GANGULY, SC
    [J]. JOURNAL OF PHYSICS PART C SOLID STATE PHYSICS, 1969, 2 (09): : 1560 - +
  • [5] Farrujia LJ., 1997, J APPL CRYSTALLOGR, V30, P565, DOI [10.1107/S0021889897003117, DOI 10.1107/S0021889897003117]
  • [6] Glusker J.P., 1994, CRYSTAL STRUCTURE AN
  • [7] Substituted trans-stilbenes, including analogues of the natural product resveratrol, inhibit the human tumor necrosis factor alpha-induced activation of transcription factor nuclear factor KappaB
    Heynekamp, Justin J.
    Weber, Waylon M.
    Hunsaker, Lucy A.
    Gonzales, Amanda M.
    Orlando, Robert A.
    Deck, Lorraine M.
    Jagt, David L. Vander
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (24) : 7182 - 7189
  • [8] PHOTOCHROMIC DIARYLETHENES WITH INTRALOCKING ARMS
    IRIE, M
    MIYATAKE, O
    UCHIDA, K
    ERIGUCHI, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (22) : 9894 - 9900
  • [9] CHEMISTRY OF SINGLET OXYGEN .52. REACTION WITH TRANS-STILBENE
    KWON, BM
    FOOTE, CS
    KHAN, SI
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (14) : 3378 - 3382
  • [10] A new class of photochromic 1,2-diarylethenes; synthesis and switching properties of bis(3-thienyl)cyclopentenes
    Lucas, LN
    van Esch, J
    Kellogg, RM
    Feringa, BL
    [J]. CHEMICAL COMMUNICATIONS, 1998, (21) : 2313 - 2314