維基百科

噻吩-3-乙酸

化合物

噻吩-3-乙酸是一種有機硫化合物，化學式為HO2CCH2C4H3S，它是白色固體，可用作有機合成的中間體。

噻吩-3-乙酸
IUPAC名
(Thiophen-3-yl)acetic acid
別名 3-TAA
3-噻吩乙酸
識別
CAS號 6964-21-2  checkY
PubChem 23404
ChemSpider 21886
SMILES
 
  • C1=CSC=C1CC(=O)O
性質
化學式 C6H6O2S
摩爾質量 142.18 g·mol⁻¹
外觀 無色或白色固體
密度 1.336 g/cm3
熔點 79—80 °C（352—353 K）[1]
pKa 4.39[2]
危險性
GHS提示詞 危險
H-術語 H314, H315, H319, H335
P-術語 P260, P261, P264, P271, P280, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P332+313
相關物質
相關化學品 吲哚-3-乙酸
呋喃-3-乙酸
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

合成

噻吩-3-乙酸可由噻吩-3-乙腈的水解得到[3]，噻吩-3-乙腈則由3-溴噻吩和氰甲基陰離子（−CH2CN）在紫外光下反應得到。[4]在四(三苯基膦)鈀的催化下和氫碘酸的存在下，噻吩-3-乙醇和一氧化碳反應，可以得到噻吩-3-乙酸，副產物是3-甲基噻吩。[5]若以噻吩-3-甲基溴化鎂為原料與二氧化碳反應，生成的主產物則是3-甲基噻吩-2-甲酸。[6]

反應

噻吩-3-乙酸和N,N'-二環己基碳二亞胺（DCC）在甲苯中反應，可以得到噻吩-3-乙酸酐：[7]

 

在硫酸催化下，它在甲醇中回流，可以得到噻吩-3-乙酸甲酯。[8]

 

在四氯化鋯催化下，它和苄胺在二甲基甲酰胺中反應，可以得到N-苄基噻吩-3-乙酰胺。[9]它和2-溴苯甲醛（法語：2-Bromobenzaldéhyde）在碳酸鉀和鈀催化劑的存在下反應，可以得到萘並[1,2-b]噻吩-4-甲酸。[10]它和氯化亞碸反應，得到噻吩-3-乙酰氯。[11]

參考文獻

  1. ^ Campaigne, E.; LeSuer, William M. 3-Substituted Thiophenes. I. Journal of the American Chemical Society (American Chemical Society (ACS)). 1948, 70 (4): 1555–1558. ISSN 0002-7863. doi:10.1021/ja01184a078 （英語）. 
  2. ^ Demessence, Aude; Rogez, Guillaume; Rabu, Pierre. Grafting of Thiophenecarboxylates into Magnetic Transition Metal Hydroxide Layers. Chemistry of Materials (American Chemical Society (ACS)). 2006, 18 (13): 3005–3015. ISSN 0897-4756. doi:10.1021/cm060366w （英語）. 
  3. ^ Menghin, Sonja. Analogs of histaprodifen as potent and selective agonists of the histamine H1-receptor. Synthesis, pharmacological characterization, and structure-activity relationships [dissertation]. [Ger. Diss.] D1011-1012, CAN143: 452765. 2004 （德語）. 
  4. ^ Gol'dfarb, Ya. L.; Yakubov, A. P.; Belen'kii, L. I. Novel synthesis of 3-thienylacetonitrile based on the photostimulated reaction of 3-bromothiophene with cyanomethyl anion. Khimiya Geterotsiklicheskikh Soedinenii. 1979, (8): 1044-1046. ISSN 0453-8234 （俄語）. 
  5. ^ Lin, Yong-Shou; Yamamoto, Akio. Palladium-catalyzed carbonylation of benzyl alcohol and its analogs promoted by HI in aqueous systems. Tetrahedron Letters (Elsevier BV). 1997, 38 (21): 3747–3750. ISSN 0040-4039. doi:10.1016/s0040-4039(97)00744-2 （英語）. 
  6. ^ Campaigne, E.; Yokley, O. E. 3-Substituted Thiophenes. XI. Abnormal Products from 3-Thenyl Grignard Reagents1. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1963, 28 (4): 914–917. ISSN 0022-3263. doi:10.1021/jo01039a008 （英語）. 
  7. ^ Barrios Antúnez, Diego-Javier; Greenhalgh, Mark D.; Brueckner, Alexander C.; Walden, Daniel M.; Elías-Rodríguez, Pilar; Roberts, Patrick; Young, Benjamin G.; West, Thomas H.; Slawin, Alexandra M. Z.; Ha-Yeon Cheong, Paul; Smith, Andrew D. Catalytic enantioselective synthesis of perfluoroalkyl-substituted β-lactones via a concerted asynchronous [2 + 2] cycloaddition: a synthetic and computational study. Chemical Science (Royal Society of Chemistry (RSC)). 2019, 10 (24): 6162–6173. ISSN 2041-6520. doi:10.1039/c9sc00390h （英語）. 
  8. ^ Brembilla, A.; Collard, A.; Henry, B.; Jadamiec, M.; Lapkowski, M.; Matlengiewicz, M.; Rodehüser, L. Synthesis of Functionalized Thiophenes for the Preparation of Conducting Polymer Films with Complexing Properties. Phosphorus, Sulfur, and Silicon and the Related Elements (Informa UK Limited). 2007-02-15, 182 (4): 723–734. ISSN 1042-6507. doi:10.1080/10426500601047503 （英語）. 
  9. ^ Lundberg, Helena; Tinnis, Fredrik; Adolfsson, Hans. Direct Amide Coupling of Non-activated Carboxylic Acids and Amines Catalysed by Zirconium(IV) Chloride. Chemistry - A European Journal (Wiley). 2012-02-24, 18 (13): 3822–3826. ISSN 0947-6539. doi:10.1002/chem.201104055 （英語）. 
  10. ^ Nitti, Andrea; Osw, Peshawa; Calcagno, Giuseppe; Botta, Chiara; Etkind, Samuel I.; Bianchi, Gabriele; Po, Riccardo; Swager, Timothy M.; Pasini, Dario. One-Pot Regiodirected Annulations for the Rapid Synthesis of π-Extended Oligomers. Organic Letters (American Chemical Society (ACS)). 2020-04-07, 22 (8): 3263–3267. ISSN 1523-7060. doi:10.1021/acs.orglett.0c01043 （英語）. 
  11. ^ Lee-Ruff, E.; Ablenas, Fred J. Acid-catalyzed rearrangement of cyclobutanols. A novel rearrangement. Canadian Journal of Chemistry (Canadian Science Publishing). 1987-07-01, 65 (7): 1663–1667. ISSN 0008-4042. doi:10.1139/v87-278 （英語）. 

拓展閱讀

  • Ben Issa, Takoua; Sagaama, Abir; Issaoui, Noureddine. Computational study of 3-thiophene acetic acid: Molecular docking, electronic and intermolecular interactions investigations. Computational Biology and Chemistry (Elsevier BV). 2020, 86: 107268. ISSN 1476-9271. doi:10.1016/j.compbiolchem.2020.107268 （英語）. 
  • Temprado, Manuel; Roux, María Victoria; Jiménez, Pilar; Foces-Foces, Concepción; Notario, Rafael. Thermochemistry of 2- and 3-Thiopheneacetic Acids: Calorimetric and Computational Study. The Journal of Physical Chemistry A (American Chemical Society (ACS)). 2008-09-25, 112 (41): 10378–10385. ISSN 1089-5639. doi:10.1021/jp804672d （英語）. 

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