[4-((E)-Styryl)-benzyl]-phosphonic acid diethyl ester | 63842-16-0

• 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: [4-((E)-Styryl)-benzyl]-phosphonic acid diethyl ester
• 英文别名: 1-(diethoxyphosphorylmethyl)-4-(2-phenylethenyl)benzene
• CAS: 63842-16-0
• 化学式: C₁₉H₂₃O₃P
• 分子量: 330.364
• InChiKey: MBDWOOJOETWDHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [4-((E)-Styryl)-benzyl]-phosphonic acid diethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以50%的产率得到4-phenylethyl benzylphosphonate de diethyle
  参考文献：
  名称：

  Évaluation de l'activité inhibitrice calcique d'une série de benzylphosphonates de diéthyle

  摘要：

  Thirty-nine diethyl benzylphosphonates related to Fostedil were evaluated as calcium antagonists, using the inhibition test on aortic contraction in the rabbit, which was more selective than the negative inotropic activity test on guinea-pig left atrial muscle. Six compounds were found to have weak activity compared with Fostedil. Structure-activity relationships indicated a certain lipophilic influence; no correlation was found with electronic parameters. The prerequisite structure to obtain active products seems to require 2 conjugated aromatic rings separated by an optimal distance.

  DOI：

  10.1016/0223-5234(92)90120-p
• 作为产物：
  描述：

  反式-BETA-苯乙烯硼酸 、 (4-碘苄基)膦酸二乙酯 在 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 [4-((E)-Styryl)-benzyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Unsymmetric indolylmaleimides: Synthesis, photophysical properties and amyloid detection

  摘要：

  Various unsymmetric indolylmaleimides were synthesized. Their photophysical properties and affinities for amyloid fibrils were evaluated. Some unsymmetric indolylmaleimides have large Stokes shifts of more than 120 nm, fluorescence emission maxima wavelengths of more than 550 nm and different emissions under UV irradiation at 365 nm. From the results of histopathologic methods using stains, 3-(1H-indol-3-yl)-1-methyl-4-phenyl-1H-pyrrole-2,5-dione has high selectivity for amyloid fibrils in senile systemic amyloidosis. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2014.04.027

文献信息

• Water-Soluble Distyrylbenzenes: One Core with Two Sensory Responses-Turn-On and Ratiometric
  作者：Juan Tolosa、Jonathan J. Bryant、Kyril M. Solntsev、Kerstin Brödner、Laren M. Tolbert、Uwe H. F. Bunz

  DOI：10.1002/chem.201102402

  日期：2011.12.2

  The synthesis of four water‐soluble distyrylbenzenes (compounds 1–4) is reported. Their acidochromicity in aqueous media was investigated. Blue shifts and increases in the quantum yields were observed as a general response. The pH‐dependent photophysics of 1 b–3 b in water reveal unexpected protonation sequences upon titration: compound 1 b is green–yellow fluorescent at high pH (10) but becomes very

  四个水溶性二苯乙烯基苯（化合物的合成1 - 4报道）。研究了它们在水性介质中的酸致变色性。观察到蓝移和量子产率的增加是普遍的反应。水中1 b – 3 b的pH依赖性光物理性质在滴定时显示出意外的质子化序列：化合物1 b在高pH（10）时呈绿黄色荧光，但在pH 5和pH 3之间却变为弱荧光，而在pH 2以下观察到强烈的蓝色荧光。可以用苯胺和羧酸酯基的质子相互作用来解释这种行为。在化合物4中，观察到较高的氨基碱性，并且在质子化或与水中的锌盐反应时，荧光荧光发生比例变化。因此，即使化合物4仅具有二甲基氨基单元作为结合基序，其也可以在水中用作弱比例锌配体。
• Phenolic Bis-styrylbenzenes as β-Amyloid Binding Ligands and Free Radical Scavengers
  作者：Daniel P. Flaherty、Tomomi Kiyota、Yuxiang Dong、Tsuneya Ikezu、Jonathan L. Vennerstrom

  DOI：10.1021/jm1006929

  日期：2010.11.25

  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.
• Erckel, R.; Fruehbeis, H., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 11, p. 1472 - 1480
  作者：Erckel, R.、Fruehbeis, H.

  DOI：——

  日期：——