(E)-5-[2-(4-dimethylaminophenyl)-vinyl]-thiophene-2-carbaldehyde | 287958-61-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-5-[2-(4-dimethylaminophenyl)-vinyl]-thiophene-2-carbaldehyde
• 英文别名: trans-5-(4-(dimethylamino)styryl)thiophene-2-carbaldehyde；5-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]thiophene-2-carbaldehyde
• CAS: 287958-61-6
• 化学式: C₁₅H₁₅NOS
• 分子量: 257.356
• InChiKey: ZXADMJYHANXTGK-VMPITWQZSA-N

物化性质

• 沸点：
  438.9±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-[2-(4-dimethylaminophenyl)-vinyl]-thiophene-2-carbaldehyde 、 2-甲基苯并噻唑 在 氢氧化钾 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 以79%的产率得到(E,E)-2-(2-{5-[2-(4-dimethylaminophenyl)-vinyl]-thiophen-2-yl}-vinyl)-benzothiazole
  参考文献：
  名称：

  Donor–π-acceptor benzothiazole-derived dyes with an extended heteroaryl-containing conjugated system: synthesis, DFT study and antimicrobial activity

  摘要：

  A series of novel derivatives containing an electron-donating N,N-dimethylaminophenyl ring connected to an electron-withdrawing benzothiazole or benzothiazolium moiety via a heteroaryl system (furan, thiophene or N-methylpyrrole) and up to two ethenylene groups have been synthesized and characterized. Furthermore, their nonlinear optical (NLO) properties have been investigated at the theoretical level using DFT and time-dependent DFT methods, and their antimicrobial activities were evaluated against a standard set of unicellular organisms. Both benzothiazole and benzothiazolium systems are predicted to exhibit large NLO responses, based on the calculated static molecular quadratic hyper-polarizabilities beta(0) as well as intramolecular charge transfer (ICT) transition characteristics. Moreover, the 3-alkyl-benzothiazolium salts were found to display high toxicity against several tested microbes. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.08.064
• 作为产物：
  描述：

  2-(噻吩甲基)膦酸二乙酯 在 potassium tert-butylate 作用下， 生成 (E)-5-[2-(4-dimethylaminophenyl)-vinyl]-thiophene-2-carbaldehyde
  参考文献：
  名称：

  Donor–acceptor molecules containing thiophene chromophore: synthesis, spectroscopic study and electrogenerated chemiluminescence

  摘要：

  Donor-acceptor molecules containing thiophene chromophore with remarkably large Stokes shift (> 210 nm) have been found to exhibit strong and stable ECL emission via the singlet excited state without the addition of any co-reactant or a second compound. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.154

文献信息

• New Uncharged 2-Thienostilbene Oximes as Reactivators of Organophosphate-Inhibited Cholinesterases
  作者：Milena Mlakić、Tena Čadež、Danijela Barić、Ivana Puček、Ana Ratković、Željko Marinić、Kornelija Lasić、Zrinka Kovarik、Irena Škorić

  DOI：10.3390/ph14111147

  日期：——

  comprises an antimuscarinic drug and an oxime reactivator of the inhibited enzyme. Oximes in use have quaternary nitrogens, and therefore poorly cross the brain–blood barrier. In this work, we synthesized novel uncharged thienostilbene oximes by the Wittig reaction, converted to aldehydes by Vilsmeier formylation, and transformed to the corresponding uncharged oximes in very high yields. Eight trans,anti-

  作为神经毒剂和杀虫剂的有机磷 (OP) 对乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BChE) 的抑制会损害外周和中枢神经系统 (CNS) 中的正常胆碱能神经信号转导，从而导致胆碱能危象。治疗包括抗毒蕈碱药物和被抑制酶的肟再活化剂。使用中的肟含有季氮，因此很难穿过脑血屏障。在这项工作中，我们通过 Wittig 反应合成了新型不带电荷的噻吩并芪肟，通过 Vilsmeier 甲酰化转化为醛，并以非常高的产率转化为相应的不带电荷的肟。八反、反和反、同肟的异构体作为神经毒剂抑制的 AChE 和 BChE 的再活化剂进行了测试。四种衍生物在两小时内重新激活环沙林抑制的 BChE 高达 70%，对接研究证实了它们与环沙林抑制的 BChE 活性位点的有效相互作用。基于 AChE 和 BChE 对所有选定肟的中等结合亲和力，并在计算机上评估了 ADME 在亲脂性和 CNS 活性方面​​的特性，这些化合物呈现出一类新的肟，具有进一步开发
• Linear and Nonlinear Optical Properties of Diiron μ-Vinylcarbyne Acceptor and Stilbenyl Donor Based Chromophores
  作者：Tony Farrell、Timo Meyer-Friedrichsen、Jürgen Heck、Anthony R. Manning

  DOI：10.1021/om000112z

  日期：2000.8.1

  Ionic [(CpFeCO)2(μ-CO)(μ-CCHCH−)]+ fragments were used as electron acceptors in combination with para-substituted stilbenyl donors to form push−pull chromophores. These μ-vinylcarbyne salts were prepared by two complementary procedures:  (a) the direct condensation of the μ-ethylidyne complex [(CpFeCO)2(μ-CO)(μ-CCH3)][BF4] with various stilbenyl aldehydes and (b) the preparation and reaction of the

  离子[（CpFeCO）2（μ-CO）（μ- CCHCH-）] +片段与对位取代的苯乙烯基供体结合用作电子受体，形成推挽发色团。由两个互补的方法制备这些μ-vinylcarbyne盐：（1）直接缩合的μ-乙川配合物[（CpFeCO）2（μ-CO）（μ-CCH 3）] [BF 4 ]与各种芪醛和（b）该制备和中性醛[（CpFeCO）的反应2（μ-CO）（μ-C CHCH 2 C ^ 6 ħ 4 CHO）]与维悌希试剂，接着使用由氢化物提取[PH 3 C] [BF4 ]。尽管该系列确实表现出很高的非线性活性（通过超瑞利散射技术测量），但荧光检查显示由于双光子吸收，在二次谐波信号附近存在发射带。
• US5272218A
  申请人：——

  公开号：US5272218A

  公开（公告）日：1993-12-21
• US9636424B2
  申请人：——

  公开号：US9636424B2

  公开（公告）日：2017-05-02
• Donor–π-acceptor benzothiazole-derived dyes with an extended heteroaryl-containing conjugated system: synthesis, DFT study and antimicrobial activity
  作者：Marián Zajac、Peter Hrobárik、Peter Magdolen、Pavlína Foltínová、Pavol Zahradník

  DOI：10.1016/j.tet.2008.08.064

  日期：2008.11

  A series of novel derivatives containing an electron-donating N,N-dimethylaminophenyl ring connected to an electron-withdrawing benzothiazole or benzothiazolium moiety via a heteroaryl system (furan, thiophene or N-methylpyrrole) and up to two ethenylene groups have been synthesized and characterized. Furthermore, their nonlinear optical (NLO) properties have been investigated at the theoretical level using DFT and time-dependent DFT methods, and their antimicrobial activities were evaluated against a standard set of unicellular organisms. Both benzothiazole and benzothiazolium systems are predicted to exhibit large NLO responses, based on the calculated static molecular quadratic hyper-polarizabilities beta(0) as well as intramolecular charge transfer (ICT) transition characteristics. Moreover, the 3-alkyl-benzothiazolium salts were found to display high toxicity against several tested microbes. (c) 2008 Elsevier Ltd. All rights reserved.