5-formyl-5'-(piperidin-1-yl)-2,2'-bithiophene | 174285-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-formyl-5'-(piperidin-1-yl)-2,2'-bithiophene
• 英文别名: 5'-N-piperidinyl-2',5-bithiophene-2-carboxaldehyde；5-[5-(1-piperidyl)-2-thienyl]thiophene-2-carbaldehyde；5-formyl-5′-piperidino-2,2′-bithiophene；5-(5-Piperidin-1-ylthiophen-2-yl)thiophene-2-carbaldehyde
• CAS: 174285-43-9
• 化学式: C₁₄H₁₅NOS₂
• 分子量: 277.411
• InChiKey: CHXAFXNVZHBCPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-formyl-5'-(piperidin-1-yl)-2,2'-bithiophene 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 (E)-2-cyano-3-(5-piperidin-1-yl-2,2-bithien-5-yl)acrylic acid
  参考文献：
  名称：

  Metal-free synthesis of bisthiophene-core donor acceptor organic photosensitizers for dye-sensitized solar cells

  摘要：

  Three novel donor-it-acceptor molecules with a bis-thiophene core have been synthesized through a simple and versatile metal-free synthetic procedure. Study of their optical and electrochemical properties, and a preliminary evaluation of their use as dyes in dye sensitized solar cells (DSSC) are presented. The proposed synthetic protocol results in a drastic reduction of the size and complexity of the sensitizer molecule, possibly enabling cost decrease by overall yield improvement and easy scalability. Particular attention has been paid to limit the environmental impact by reducing the number of synthetic steps and especially avoiding the use of organometallic reactions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.03.100
• 作为产物：
  描述：

  piperidino-4-(2-thienyl)-4-oxobutanamide 在 劳森试剂 、 正丁基锂 作用下， 以 甲苯 为溶剂， 生成 5-formyl-5'-(piperidin-1-yl)-2,2'-bithiophene
  参考文献：
  名称：

  灵敏的 1,1-二氰基乙烯基推拉染料，用于通过荧光检测溶液中的伯胺

  摘要：

  1,1-二氰基乙烯基推挽染料PTTCN与 DMSO 溶液中的挥发性脂肪族伯胺发生快速且可逆的 aza-Michael 加成，产生高荧光亚胺衍生物。该反应伴随着显着的颜色变化以及荧光的强烈增加（增加 1200 倍），从而可以灵敏地打开检测溶液中的伯胺。在固态下，PTTCN是发射的，并且与伯胺蒸气的反应导致荧光变化和伯胺的可能比率检测。对伯胺的选择性优于对仲胺、叔胺和芳香胺以及对硫醇的选择性，荧光光谱可以区分伯胺和其他氮亲核试剂如肼和氨水。最后，作为概念验证，我们展示了荧光开启反应可用于响应食品腐败过程中释放的挥发性胺蒸气。

  DOI：

  10.1016/j.dyepig.2022.110258

文献信息

• Modeling, design and synthesis of new heteroaryl ethylenes active against the MCF-7 breast cancer cell-line
  作者：Vincenza Barresi、Carmela Bonaccorso、Giuseppe Consiglio、Laura Goracci、Nicolò Musso、Giuseppe Musumarra、Cristina Satriano、Cosimo G. Fortuna

  DOI：10.1039/c3mb70151d

  日期：——

  A dataset of 50 compounds was used to generate a QSAR model and to design 9 new heteroaryl ethylenes. These compounds were synthesized, tested in vitro and a significant agreement with in silico predictions observed. Studies using Laser Scanning Confocal Microscopy pointed out that the compounds may act by different mechanisms.

  利用 50 种化合物的数据集生成了一个 QSAR 模型，并设计出 9 种新的杂芳基乙烯。对这些化合物进行了合成和体外测试，并观察到它们与硅学预测结果非常吻合。使用激光扫描共聚焦显微镜进行的研究指出，这些化合物可能通过不同的机制发挥作用。
• Formylation, dicyanovinylation and tricyanovinylation of 5-alkoxy- and 5-amino- substituted 2,2′-bithiophenes
  作者：M.Manuela M Raposo、G Kirsch

  DOI：10.1016/s0040-4020(03)00705-1

  日期：2003.6

  Several donor–acceptor-substituted bithiophenes were synthesized by functionalization of the corresponding 5-alkoxy- or 5-aminobithiophenes 1 by different methods: Vilsmeier formylation, metalation followed by reaction with DMF, direct tricyanovinylation reaction using TCNE or Knoevenagel condensation starting from the corresponding 5-formyl- derivatives of 1.

  几个供体-受体取代bithiophenes通过的官能化合成相应的5-烷氧基-或5- aminobithiophenes 1通过不同的方法：维尔斯迈尔甲酰化，金属化，随后用DMF，使用TCNE或Knoevenagel缩合从相应的5-开始直接tricyanovinylation反应反应的甲酰基衍生物1。
• (<i>E</i>)-2-Cyano-3-(5′-piperidin-1-yl-2,2′-bithien-5-yl)acrylic Acid: A Fluorescent Probe for Detecting Prefibrillar Oligomers
  作者：Francesco Attanasio、Carmela Bonaccorso、Francesco Bellia、Sebastiano Cataldo、Cosimo G. Fortuna、Giuseppe Musumarra、Bruno Pignataro、Enrico Rizzarelli

  DOI：10.1002/ejoc.201300241

  日期：2013.6

  The synthesis of (E)-2-cyano-3-(5′-piperidin-1-yl-2,2′-bithien-5-yl)acrylic acid, a novel amyloid aggregation fluorescent probe, is reported. This new probe is able to monitor soluble oligomeric aggregates after 24 h, at which time Thioflavin T emission, commonly used to monitor amyloid fibril formation, remains unchanged. Atomic force microscopy, native polyacrylamide gel electrophoresis, and dynamic

  报道了 (E)-2-cyano-3-(5'-piperidin-1-yl-2,2'-bithien-5-yl) 丙烯酸，一种新型淀粉样蛋白聚集荧光探针的合成。这种新探针能够在 24 小时后监测可溶性寡聚聚集体，此时通常用于监测淀粉样蛋白原纤维形成的硫磺素 T 发射保持不变。原子力显微镜、天然聚丙烯酰胺凝胶电泳和动态光散射证实聚集的早期阶段是不具有淀粉样蛋白结构的前原纤维寡聚物种。这种新的分子支架扩展了用于鉴定原纤维前寡聚体的荧光探针工具箱，这在旨在早期检测表征所谓蛋白质错误折叠疾病的可溶性有毒聚集体的研究中是必需的。
• Synthesis of new fluorescent 2-(2′,2″-bithienyl)-1,3-benzothiazoles
  作者：Rosa M.F. Batista、Susana P.G. Costa、M.Manuela M. Raposo

  DOI：10.1016/j.tetlet.2004.02.048

  日期：2004.3

  Bithienyl-1,3-benzothiazole derivatives were synthesised by reacting various 5-formyl-5′-alkoxy- or 5-formyl-5′-N,N-dialkylamino-2,2′-bithiophenes with ortho-aminobenzenethiol in good to excellent yields. Evaluation of the fluorescence properties of these compounds was carried out. They show strong fluorescence in the 450–600 nm region, as well as high quantum yields and large Stokes’ shifts.

  通过使各种5-甲酰基-5'-烷氧基-或5-甲酰基-5'- N，N-二烷基氨基-2,2'-联噻吩与邻-氨基苯硫醇良好或优异地反应来合成Bithienyl-1,3-苯并噻唑衍生物产量。评估这些化合物的荧光性质。它们在450-600 nm区域显示强荧光，并具有高量子产率和较大的斯托克斯位移。
• Photoinduced Intramolecular Charge Transfer and Hyperpolarizability Coefficient in Push-Pull Pyridinium Salts with Increasing Strength of the Acceptor Group
  作者：Alessio Cesaretti、Carmela Bonaccorso、Fausto Elisei、Cosimo G. Fortuna、Letizia Mencaroni、Anna Spalletti

  DOI：10.1002/cplu.201800393

  日期：2018.11

  The synthesis of three push-pull cationic dyes is reported here together with a photophysical study carried out by stationary and ultrafast spectroscopies. The hyperpolarizability (β) values of the three molecules have been estimated through a simple solvatochromic method based on conventional, low-cost equipment, which had been tested previously with success in our laboratory. The investigated pyridinium

  此处报道了三种推挽阳离子染料的合成，以及通过固定和超快光谱学进行的光物理研究。这三种分子的超极化率（β）值是通过基于常规低成本设备的简单溶剂变色方法估算的，该方法先前已经在我们的实验室中成功进行了测试。所研究的吡啶鎓盐显示出很强的负溶剂变色性，与一个强电子给体基团具有相同的哌啶环，并且与富电子的π-连接基具有相同的噻吩，但在电子受体吡啶鎓单元上的N-取代基不同，即化合物A中的N-甲基，B中的N-嘧啶-2yl和C中的N-2,4-二硝基苯基。发现衍生的β值增加（顺序为A