(E,E)-1,4-bis(2'-hydroxystyryl)benzene | 65614-65-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E,E)-1,4-bis(2'-hydroxystyryl)benzene
• 英文别名: 2-[(E)-2-[4-[(E)-2-(2-hydroxyphenyl)ethenyl]phenyl]ethenyl]phenol
• CAS: 65614-65-5
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: IKQWYCXCJIYQMB-WXUKJITCSA-N

物化性质

• 熔点：
  262-265 °C
• 沸点：
  525.5±45.0 °C(predicted)
• 密度：
  1.244±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E,E)-1,4-bis(2'-hydroxystyryl)benzene 、 p-toluenesulfonyl-4-O-{(2-(E)-{4-[2-(2-benzyloxyphenyl)-(E)-vinyl]phenyl}vinyl)phenyl}-2,3-O-isopropylidene-L-threitol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以64%的产率得到1-[O-2-(2-(E)-{4-[2-(E)-(2-hydroxyphenyl)vinyl]phenyl}vinyl)phenyl]-4-[O-2-(2-(E)-{4-[2-(E)-(2-benzyloxyphenyl)vinyl]phenyl}vnyl)phenyl]-2,3-[O-isopropylidene]-L-threitol
  参考文献：
  名称：

  Alternating Oligo[(2,3-O-isopropylidene-l-threitol)]-co-[(E,E)-1,4-bis(styryl)benzene]s: The Linear Chirality Transmisson Additivity Relationship in Nematic Liquid Crystals

  摘要：

  Alternating oligo[2,3-O-isopropylidene-L-threitol]-co-[(E,E)-1,4-bis(styryl)benzene]s (denoted as 2-6 in the article) show helical twisting power (HTP), in 4-pentoxyl-4'-biphenylcarbonitrile (5OCB), linearly proportional to the number of the chiral cores in the oligomers. The HTP per chiral core of -1.75 mu m(-1) was recorded in the correlation plot with a correlation coefficient of R = 0.99. These results suggested that the C, chiral L-threitol cores are aligned along the same axis. The comparable linear dichroism (LD) of 0.42 +/- 0.02 obtained for (rac)-2-5 at 405 rim, and of 0.52 +/- 0.03 for E7, a commercially available room temperature nematic solvent, at 347 nm in a parallel rubbed cell indicated that the long axis of the bis(styryl)benzene segments is more or less parallel to the director of the E7 in the LC matrix. This observation is highly exciting because the HTP per core Could still be maintained, no matter whether the cores are evenly spread in a form of monomer in the LC matrix or tightly confined in a polymer. Theoretical treatments about the conformations of the dopant in the nematic matrix are discussed.

  DOI：

  10.1021/jp909286t
• 作为产物：
  描述：

  1,4-bis((E)-2-(methoxymethoxy)styryl)benzene 在 盐酸 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 24.0h， 以64%的产率得到(E,E)-1,4-bis(2'-hydroxystyryl)benzene
  参考文献：
  名称：

  Phenolic Bis-styrylbenzenes as β-Amyloid Binding Ligands and Free Radical Scavengers

  摘要：

  Starting from bisphenolic bis-styrylbenzene DF-9 (4), P-amyloid (A beta) binding affinity and specificity for phenolic bis-styrylbenzenes, monostyrylbenzenes, and alkyne controls were determined by fluorescence titration with beta-amyloid peptide A beta(1-40) and a fluorescence assay using APP/PSI transgenic mouse brain sections. Bis-styrylbenzene SA R is derived largely from work on symmetrical compounds. This study is the first to describe A beta binding data for bis-styrylbenzenes unsymmetrical in the outer rings. With one exception, binding affinity and specificity were decreased by adding and/or changing the substitution pattern of phenol functional groups, changing the orientation about the central phenyl ring, replacing the alkene with alkyne bonds, or eliminating the central phenyl ring. The only compound with an A beta binding affinity and specificity comparable to 4 was its 3-hydroxy regioisomer 8. Like 4, 8 crossed the blood brain barrier and bound to A beta plaques in vivo. By use of a DPPH assay, phenol functional groups with papa orientations seem to be a necessary. but insufficient, criterion for good free radical scavenging properties in these compounds.

  DOI：

  10.1021/jm1006929

文献信息

• Tewari,R.S. et al., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1977, vol. 15B, p. 753 - 755
  作者：Tewari,R.S. et al.

  DOI：——

  日期：——
• TEWARI R. S.; KUMARI N.; KENDURKAR P. S., INDIAN J. CHEM., 1977, B15, NO 8, 753-755
  作者：TEWARI R. S.、 KUMARI N.、 KENDURKAR P. S.

  DOI：——

  日期：——