5-[2-(p-nitrophenyl)vinyl]-2-thiophenecarbaldehyde | 67248-95-7

• 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: 5-[2-(p-nitrophenyl)vinyl]-2-thiophenecarbaldehyde
• 英文别名: trans-5-(4-nitrostyryl)thiophene-2-carbaldehyde；5-[(E)-2-(4-nitrophenyl)ethenyl]thiophene-2-carbaldehyde
• CAS: 67248-95-7
• 化学式: C₁₃H₉NO₃S
• 分子量: 259.285
• InChiKey: QDJSHNXMMVXXFQ-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[2-(p-nitrophenyl)vinyl]-2-thiophenecarbaldehyde 以50%的产率得到
  参考文献：
  名称：

  YOSHIMURA S.; TAKAHASHI S.; KAWAMATA A.; KIKUGAWA K.; SUEHIRO H.; AOKI A., CHEM. AND PHARM. BULL., 1978, 26, NO 3, 685-702

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl (4-nitrobenzyl)phosphonate 在 potassium tert-butylate 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 5-[2-(p-nitrophenyl)vinyl]-2-thiophenecarbaldehyde
  参考文献：
  名称：

  Wu, Wei; Zhang, Zhaoli; Zhang, Xiaoyun, Journal of Chemical Research, 2004, # 9, p. 617 - 619

  摘要：

  DOI：

文献信息

• Synthesis of novel conjugated oligomers for second-order nonlinear optics: incorporation of a central spacer as a conjugation modulator
  作者：Jian Xin Zhang、Philippe Dubois、Robert Jérôme

  DOI：10.1039/a606547c

  日期：——

  A new series of second-order nonlinear optical chromophores has been synthesized that consists of a conjugated segment end-capped with an electron acceptor and an electron donor, respectively, and a central spacer intended to modulate the electro-optical effect. Conjugated chains have been tailored with trans-vinylene-1,5-thienylene as the building unit and N,N-dimethylamino and nitro groups as the donor–acceptor pair. Four spacers have been incorporated into the central part of the conjugated oligomers, which range from saturated to totally unsaturated functions, i.e. from methylene to vinylene units. The general strategy relies upon two consecutive Wittig or Wittig–Horner reactions between the spacer precursor and an aromatic phosphonium or phosphonate bearing the strong electron donor and the acceptor, respectively. Two synthetic pathways have been studied. The first procedure is based on the use of a symmetric precursor for the spacer. However, a reaction byproduct is formed, which must be removed and decreases the reaction efficiency. The second approach requires an asymmetric precursor for the spacer, the synthesis of which is a multistep process. In order to evaluate the effect of the spacer, a completely conjugated oligomer has been prepared by the one-step coupling of two conjugated segments end-functionalized by the electron donor and the acceptor, respectively.

  一种新的二阶非线性光学染料系列已被合成，该系列由一个共轭段组成，两端分别封端为电子受体和电子给体，并包含一个中心间隔器，旨在调节电光效应。共轭链使用反式乙烯-1,5-噻吩单元作为构建单元，N,N-二甲基氨基和硝基作为给体–受体对。四种间隔器被引入到共轭 oligomer 的中央部分，这些间隔器从饱和功能到完全不饱和功能，即从亚甲基到乙烯基单元。一般策略依赖于间隔器前体与带有强电子给体和受体的芳香族膦盐或膦酸酯之间的两次连续 Wittig 或 Wittig–Horner 反应。研究了两条合成路径。第一种程序基于使用对称前体作为间隔器。然而，会形成一个反应副产物，必须去除，这降低了反应效率。第二种方法需要不对称的间隔器前体，其合成是一个多步过程。为了评估间隔器的影响，通过将两个分别被电子给体和受体功能化的共轭段进行一步耦合，制备了一个完全共轭的 oligomer。
• 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
• Synthesis and properties of push–pull chromophores for second-order nonlinear optics derived from π-extended tetrathiafulvalenes (TTFs)
  作者：Manuel Otero、Ma Ángeles Herranz、Carlos Seoane、Nazario Martı́n、Javier Garı́n、Jesús Orduna、Rafael Alcalá、Belén Villacampa

  DOI：10.1016/s0040-4020(02)00803-7

  日期：2002.9

  (EFISH technique) studied. The redox properties of the novel compounds have been investigated by cyclic voltammetry (CV) and the CV data reveal the good donor ability of the exTTF unit. Although the energy of the intramolecular charge-transfer (ICT) band displayed by these compounds and their redox potentials are fairly insensitive to the nature of the conjugated spacer linking the donor and the acceptor

  通过π共轭低烯间隔基（14a – c – 16a – c）连接到对硝基苯基电子接受单元的新型π扩展四硫富瓦烯（exTTF）衍生物显示出良好的二阶光学非线性。寡烯间隔子的共轭长度和π共轭桥中噻吩环的存在（20a – c）已在理论上（PM3）和/或实验上（EFISH技术）进行了研究。已通过循环伏安法（CV）研究了新型化合物的氧化还原特性，并且CV数据显示了exTTF单元的良好供体能力。虽然这些化合物显示的分子内电荷转移（ICT）谱带的能量及其氧化还原电位对连接供体和受体部分的共轭间隔基的性质相当不敏感，但观察到其二阶非线性光学响应有所增加在增加共轭长度上。带有噻吩环的化合物20a – c具有出色的热稳定性，分解温度超过400°C。一系列新的D-π-A化合物（23a – c）还合成和研究了带有1，3-二硫醇-2-亚烷基供体单元的）。
• Synthesis and characterization of end-functionalized oligo(vinylthiophenes) with liquid crystal properties
  作者：Christophe Maertens、Jian-Xin Zhang、Philippe Dubois、Robert Jérôme

  DOI：10.1039/p29960000713

  日期：——

  A general scheme for the synthesis of end-functionalized conjugated (E)-vinylthiophene oligomers with liquid crystal and potential second-order non-linear optical properties is described, These push-pull thiophene-containing aromatic molecules show mesogenic properties over different temperature ranges depending on the chain length and the functional end-groups.
• Wu, Wei; Zhang, Zhaoli; Zhang, Xiaoyun, Journal of Chemical Research, 2004, # 9, p. 617 - 619
  作者：Wu, Wei、Zhang, Zhaoli、Zhang, Xiaoyun

  DOI：——

  日期：——