dimethyl 5,5'-[(1E,1'E)-(2-fluoro-1,4-phenylene)bis(ethene-2,1-diyl)]bis(2-methoxybenzoate) | 760987-96-0

• 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: dimethyl 5,5'-[(1E,1'E)-(2-fluoro-1,4-phenylene)bis(ethene-2,1-diyl)]bis(2-methoxybenzoate)
• 英文别名: (E,E)-1-fluoro-2,5-bis(3-methoxycarbonyl-4-methoxystyryl)benzene；methyl 5-[(E)-2-[3-fluoro-4-[(E)-2-(4-methoxy-3-methoxycarbonylphenyl)ethenyl]phenyl]ethenyl]-2-methoxybenzoate
• CAS: 760987-96-0
• 化学式: C₂₈H₂₅FO₆
• 分子量: 476.501
• InChiKey: YWWHSEDUHMWZNA-LCAICKDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 5,5'-[(1E,1'E)-(2-fluoro-1,4-phenylene)bis(ethene-2,1-diyl)]bis(2-methoxybenzoate) 在 三溴化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Isotope-Labeling of the Fibril Binding Compound FSB via a Pd-Catalyzed Double Alkoxycarbonylation

  摘要：

  We have synthesized two isotopically labeled variants of the beta-amyloid binding compound FSB possessing C-13-labels on the two terminal aryl carboxylic acid moieties. One of these was also fully deuterated on the olefinic spacers. The C-13-isotope labeling was achieved applying a Pd-catalyzed methoxycarbonylation of the corresponding aryl chlorides with externally (ex situ) generated C-13-labeled CO. Application of the Shirakawa-Hayashi protocol for the Pd-catalyzed reduction of a dialkyne intermediate using D2O allowed for the selective deuterium labeling of the two trans-C,C double bonds of FSB.

  DOI：

  10.1021/jo300746x
• 作为产物：
  描述：

  1,4-二(溴甲基)-2-氟-苯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 dimethyl 5,5'-[(1E,1'E)-(2-fluoro-1,4-phenylene)bis(ethene-2,1-diyl)]bis(2-methoxybenzoate)
  参考文献：
  名称：

  Fluoro-substituted and 13C-labeled styrylbenzene derivatives for detecting brain amyloid plaques

  摘要：

  Two styrylbenzene derivatives, (E,E)-1-fluoro-2,5-bis-(3-hydroxycarbonyl-4-hydroxy)styrylbenzene (FSB) and (EE)-1-bromo-2,5-bis(3-hydroxycarbonyl-4-hydroxy)styrylbenzene-alpha,alpha'-C-13(2) ([C-13]BSB), were synthesized for use as a histochemical stain to detect amyloid plaques of Alzheimer's disease (AD) brain sections. An analysis of fluorescence spectra demonstrated that FSB shows approximately twofold fluorescence intensity relative to the conventional styrylbenzene derivative, (EE)-1-bromo-2,5-bis-(3-hydroxycarbonyl-4-hydroxy) styrylbenzene (BSB). Moreover, FSB was found to stain amyloid plaques and neurofibrillary tangles of AD brains with greater fluorescence intensity and a lower level of background signals compared to BSB. These finding indicate that FSB can be an excellent fluorescent compound to label human amyloid lesions with high sensitivity and specificity. Because of the possession of a nuclide with a quantized angular momentum, both FSB and [C-13]BSB are also potential contrast agents for magnetic resonance imaging to locate AD pathologies in vivo. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.02.013

文献信息

• Acetamidoarenediazonium Salts: Opportunities for Multiple Arene Functionali­zation
  作者：Bernd Schmidt、Nelli Elizarov、Nastja Riemer、Frank Hölter

  DOI：10.1002/ejoc.201500795

  日期：2015.9

  Unlike their ortho counterparts, meta- and para-acetamidoanilines can be converted into the corresponding acetamidoarenediazonium salts. These offer various opportunities for multiple Pd-catalyzed arene functionalization reactions, such as Matsuda-Heck-, Suzuki-Miyaura- or Fujiwara-Moritani couplings.

  与它们的邻位对应物不同，间和对乙酰氨基苯胺可以转化为相应的乙酰氨基芳烃重氮盐。这些为多种 Pd 催化的芳烃官能化反应提供了各种机会，例如 Matsuda-Heck-、Suzuki-Miyaura- 或 Fujiwara-Moritani 偶联。