8-巰基喹啉

8-巰基喹啉
英文名	8-Mercaptoquinoline; 8-Quinolinethiol
識別
CAS號	491-33-8
PubChem	96028
ChemSpider	86692
SMILES	c1cc2cccnc2c(c1)S;
InChI	1/C9H7NS/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H;
InChIKey	MHTSJSRDFXZFHQ-UHFFFAOYAD
性質
化學式	C9H7NS
摩爾質量	161.22 g·mol⁻¹
外觀	無色固體
熔點	58.5 °C（331.6 K）
沸點	296 °C（569 K）
相關物質
相關化學品	8-羥基喹啉; 8-氨基喹啉
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

8-巰基喹啉是一種有機化合物，化學式為C₉H₇NS，它是喹啉的8號位的氫被巰基取代得到的化合物。

製備

喹啉和氯磺酸反應，得到喹啉-8-磺酰氯，它在甲苯中和三苯基膦反應，得到8-巰基喹啉。^[4]

8-溴喹啉和甲硫醇鈉反應，酸化後也能得到8-巰基喹啉。^[5]

反應

8-巰基喹啉可以作為螯合配體，和金屬化合物反應生成相應的8-巰基喹啉配位化合物，如它和四氯合金(III)酸鈉反應，可以得到8-巰基喹啉二氯化金^[6]；和二氯化二(二甲基亞碸)合鉑反應，生成LPtCl[SO(CH₃)₂]（L為8-巰基喹啉陰離子）^[7]；和二氯化二乙腈合鈀(II)反應，得到8-巰基喹啉鈀(II)，配體中的硫和氮原子共同參與配位。^[8]

8-巰基喹啉和氯化苄在碳酸鉀的存在下於N,N-二甲基甲酰胺中反應，可以得到8-苄硫基喹啉。^[9]它在乙醇溶液中和碘的氯仿溶液發生不可逆的氧化還原反應，生成(喹啉-8,8'-二硫化物)三碘化物，在該化合物中，喹啉鎓陽離子通過π-π堆積相互作用形成二聚體。^[10]它和溴乙烯反應，也能形成鎓鹽：^[11]

它和二碘甲烷發生類似反應：^[12]

參考文獻

^ Fleischer, Holger "Structural chemistry of complexes of (n - 1)d¹⁰ns^m metal ions with β-N-donor substituted thiolate ligands (m=0, 2)" Coordination Chemistry Reviews 2005, volume 249, pp. 799-827. doi:10.1016/j.ccr.2004.08.024
^ Ponci, R.; Gialdi, F. Antibacterial action of quinoline derivatives. VIII. Preparation of some thiols, sulfides, and disulfides of quinoline. Farmaco, Edizione Scientifica, 1954. 9. 459-466. ISSN: 0430-0920.
^ Bankovskis, J.; Cera, L.; Ievins, A.; Luksa, E. Analytical application of 8-quinolinethiol (thiooxine) and its derivatives. XXVII. Production of anhydrous 8-mercaptoquinoline. Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija, 1963. 2. 224-227. ISSN: 0002-3248.
^ Rao, Heng; Yu, Wen-Qian; Zheng, Hui-Qin; Bonin, Julien; Fan, Yao-Ting; Hou, Hong-Wei. Highly efficient photocatalytic hydrogen evolution from nickel quinolinethiolate complexes under visible light irradiation. Journal of Power Sources. 2016, 324: 253–260. ISSN 0378-7753. doi:10.1016/j.jpowsour.2016.05.095.
^ Zajdel, Paweł; Marciniec, Krzysztof; Maślankiewicz, Andrzej; Grychowska, Katarzyna; Satała, Grzegorz; Duszyńska, Beata; Lenda, Tomasz; Siwek, Agata; Nowak, Gabriel; Partyka, Anna; Wróbel, Dagmara; Jastrzębska-Więsek, Magdalena; Bojarski, Andrzej J.; Wesołowska, Anna; Pawłowski, Maciej. Antidepressant and antipsychotic activity of new quinoline- and isoquinoline-sulfonamide analogs of aripiprazole targeting serotonin 5-HT1A/5-HT2A/5-HT7 and dopamine D2/D3 receptors. European Journal of Medicinal Chemistry. 2013, 60: 42–50. ISSN 0223-5234. doi:10.1016/j.ejmech.2012.11.042.
^ Casado-Sánchez, Antonio; Martín-Santos, Cecilia; Padrón, José M.; Mas-Ballesté, Rubén; Navarro-Ranninger, Carmen; Alemán, José; Cabrera, Silvia. Effect of electronic and steric properties of 8-substituted quinolines in gold(III) complexes: Synthesis, electrochemistry, stability, interactions and antiproliferative studies. Journal of Inorganic Biochemistry. 2017, 174: 111–118. ISSN 0162-0134. doi:10.1016/j.jinorgbio.2017.06.004.
^ Casado-Sánchez, Antonio; Uygur, Mustafa; González-Muñoz, Daniel; Aguilar-Galindo, Fernando; Nova-Fernández, José Luis; Arranz-Plaza, Judith; Díaz-Tendero, Sergio; Cabrera, Silvia; Mancheño, Olga García; Alemán, José. 8-Mercaptoquinoline as a Ligand for Enhancing the Photocatalytic Activity of Pt(II) Coordination Complexes: Reactions and Mechanistic Insights. The Journal of Organic Chemistry. 2019, 84 (10): 6437–6447. ISSN 0022-3263. doi:10.1021/acs.joc.9b00520.
^ Moro, A. C.; Mauro, A. E.; Ananias, S. R.; Stevanato, A.; Legendre, A. O. Mono- and dinuclear palladium(II) compounds containing N,S donor ligands. Journal of Thermal Analysis and Calorimetry. 2007, 87 (3): 721–724. ISSN 1388-6150. doi:10.1007/s10973-006-7770-4.
^ Hu, Shuai; Jin, Yi; Liu, Yanghan; Ljungman, Mats; Neamati, Nouri. Synthesis and mechanistic studies of quinolin-chlorobenzothioate derivatives with proteasome inhibitory activity in pancreatic cancer cell lines. European Journal of Medicinal Chemistry. 2018, 158: 884–895. ISSN 0223-5234. doi:10.1016/j.ejmech.2018.09.037.
^ Chernov'yants, Margarita S.; Starikova, Zoya A.; Karginova, Anastasia O.; Kolesnikova, Tatiana S.; Tereznikov, Alexander Yu. Spectroscopic and structural investigation of interaction product of 8-mercaptoquinoline with molecular iodine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2013, 115: 861–865. ISSN 1386-1425. doi:10.1016/j.saa.2013.06.119.
^ Kim, J. C.; Lee, E. O.; Kim, J. D. The hemolytic characteristics of amphotericin B-containing egg PC liposomes. Yakche Hakhoechi, 1993. 23 (2): 111-118. ISSN: 0259-2347.
^ Kim, D. G.; Sokolova, S. V.; Lukina, V. V.; Volkova, S. A. Synthesis and properties of 2H-thiazolo[5,4,3-i,j]quinolinium halides. Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya, 1993. 36 (11): 107-110. ISSN: 0579-2991.

[1] Fleischer, Holger "Structural chemistry of complexes of (n - 1)d¹⁰ns^m metal ions with β-N-donor substituted thiolate ligands (m=0, 2)" Coordination Chemistry Reviews 2005, volume 249, pp. 799-827. doi:10.1016/j.ccr.2004.08.024

[2] Ponci, R.; Gialdi, F. Antibacterial action of quinoline derivatives. VIII. Preparation of some thiols, sulfides, and disulfides of quinoline. Farmaco, Edizione Scientifica, 1954. 9. 459-466. ISSN: 0430-0920.

[3] Bankovskis, J.; Cera, L.; Ievins, A.; Luksa, E. Analytical application of 8-quinolinethiol (thiooxine) and its derivatives. XXVII. Production of anhydrous 8-mercaptoquinoline. Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija, 1963. 2. 224-227. ISSN: 0002-3248.

[4] Rao, Heng; Yu, Wen-Qian; Zheng, Hui-Qin; Bonin, Julien; Fan, Yao-Ting; Hou, Hong-Wei. Highly efficient photocatalytic hydrogen evolution from nickel quinolinethiolate complexes under visible light irradiation. Journal of Power Sources. 2016, 324: 253–260. ISSN 0378-7753. doi:10.1016/j.jpowsour.2016.05.095.

[5] Zajdel, Paweł; Marciniec, Krzysztof; Maślankiewicz, Andrzej; Grychowska, Katarzyna; Satała, Grzegorz; Duszyńska, Beata; Lenda, Tomasz; Siwek, Agata; Nowak, Gabriel; Partyka, Anna; Wróbel, Dagmara; Jastrzębska-Więsek, Magdalena; Bojarski, Andrzej J.; Wesołowska, Anna; Pawłowski, Maciej. Antidepressant and antipsychotic activity of new quinoline- and isoquinoline-sulfonamide analogs of aripiprazole targeting serotonin 5-HT1A/5-HT2A/5-HT7 and dopamine D2/D3 receptors. European Journal of Medicinal Chemistry. 2013, 60: 42–50. ISSN 0223-5234. doi:10.1016/j.ejmech.2012.11.042.

[6] Casado-Sánchez, Antonio; Martín-Santos, Cecilia; Padrón, José M.; Mas-Ballesté, Rubén; Navarro-Ranninger, Carmen; Alemán, José; Cabrera, Silvia. Effect of electronic and steric properties of 8-substituted quinolines in gold(III) complexes: Synthesis, electrochemistry, stability, interactions and antiproliferative studies. Journal of Inorganic Biochemistry. 2017, 174: 111–118. ISSN 0162-0134. doi:10.1016/j.jinorgbio.2017.06.004.

[7] Casado-Sánchez, Antonio; Uygur, Mustafa; González-Muñoz, Daniel; Aguilar-Galindo, Fernando; Nova-Fernández, José Luis; Arranz-Plaza, Judith; Díaz-Tendero, Sergio; Cabrera, Silvia; Mancheño, Olga García; Alemán, José. 8-Mercaptoquinoline as a Ligand for Enhancing the Photocatalytic Activity of Pt(II) Coordination Complexes: Reactions and Mechanistic Insights. The Journal of Organic Chemistry. 2019, 84 (10): 6437–6447. ISSN 0022-3263. doi:10.1021/acs.joc.9b00520.

[8] Moro, A. C.; Mauro, A. E.; Ananias, S. R.; Stevanato, A.; Legendre, A. O. Mono- and dinuclear palladium(II) compounds containing N,S donor ligands. Journal of Thermal Analysis and Calorimetry. 2007, 87 (3): 721–724. ISSN 1388-6150. doi:10.1007/s10973-006-7770-4.

[9] Hu, Shuai; Jin, Yi; Liu, Yanghan; Ljungman, Mats; Neamati, Nouri. Synthesis and mechanistic studies of quinolin-chlorobenzothioate derivatives with proteasome inhibitory activity in pancreatic cancer cell lines. European Journal of Medicinal Chemistry. 2018, 158: 884–895. ISSN 0223-5234. doi:10.1016/j.ejmech.2018.09.037.

[10] Chernov'yants, Margarita S.; Starikova, Zoya A.; Karginova, Anastasia O.; Kolesnikova, Tatiana S.; Tereznikov, Alexander Yu. Spectroscopic and structural investigation of interaction product of 8-mercaptoquinoline with molecular iodine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2013, 115: 861–865. ISSN 1386-1425. doi:10.1016/j.saa.2013.06.119.

[11] Kim, J. C.; Lee, E. O.; Kim, J. D. The hemolytic characteristics of amphotericin B-containing egg PC liposomes. Yakche Hakhoechi, 1993. 23 (2): 111-118. ISSN: 0259-2347.

[12] Kim, D. G.; Sokolova, S. V.; Lukina, V. V.; Volkova, S. A. Synthesis and properties of 2H-thiazolo[5,4,3-i,j]quinolinium halides. Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya, 1993. 36 (11): 107-110. ISSN: 0579-2991.

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