1-萘酚(即α-萘酚)是萘的1位氢被羟基取代后形成的化合物,是2-萘酚的异构体,化学式C10H7OH。1-萘酚常温常压下为白色固体,带有荧光,其羟基的反应活性高于苯酚。1-萘酚和2-萘酚都可溶于简单的醇、醚和氯仿,可作为许多化合物的合成前体,能作为生物体多環芳香烴暴露的标识[1]。
制备
1-萘酚主要有以下两种制备方法。[2]第一种方法会先将萘硝化成1-硝基萘,然后将它氢化成1-萘胺,最后水解而成:
- C
10H
8 + HNO
3 → C
10H
7NO
2 + H
2O
- C
10H
7NO
2 + 3H
2 → C
10H
7NH
2 + 2H
2O
- C
10H
7NH
2 + H
2O → C
10H
7OH + NH
3
第二种方法则是先把萘氢化成四氢萘,然后氧化成1-四氢萘酮,最后脱氢,得到1-萘酚。
应用
1-萘酚可用于生产甲萘威等杀虫剂,以及纳多洛尔[3][4]、舍曲林[5]、阿托喹酮等药物[6]。1-萘酚可以参与重氮偶联反应,生成偶氮染料,但这些偶氮染料的用处通常比源自2-萘酚的偶氮染料少[2][7]。
参考文献
- ^ Sreekanth, R; Prasanthkumar, KP; Sunil Paul, MM; Aravind, UK; Aravindakumar, CT. Oxidation reactions of 1- and 2-naphthols: an experimental and theoretical study.. The Journal of Physical Chemistry A. 7 November 2013, 117 (44): 11261–70. PMID 24093754. doi:10.1021/jp4081355.
- ^ 2.0 2.1 Booth, Gerald, Naphthalene Derivatives, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a17_009 . full-text PDF (页面存档备份,存于互联网档案馆)
- ^ M.E. Condon; et al. Nondepressant β-adrenergic blocking agents. 1. Substituted 3-amino-1-(5,6,7,8-tetrahydro-1-naphthoxy)-2-propanols. Journal of Medicinal Chemistry. 1978, 21 (9): 913–922. PMID 31485. doi:10.1021/jm00207a014 (德语).
- ^ DE 2258995,F.R. Hauck, C.M. Cimarusti, V.L. Narayan,「2,3-cis-1,2,3,4-Tetrahydro-5[2-hydroxy-3-(tert.-butylamino)-propoxy]-2,3-naphthalindiol」,发表于1973-06-07
- ^ K. Vukics; T. Fodor; J. Fischer; I. Fellevári; S. Lévai, Improved industrial synthesis of antidepressant Sertraline, Org. Process Res. Dev. 6 (1), 2002, 6 (1): 82–85, doi:10.1021/op0100549 (德语)
- ^ B.N. Roy; G.P. Singh; P.S. Lathi; M.K. Agarwal. A novel process for synthesis of Atovaquone (PDF). Indian J. Chem. 2013, 52B: 1299–1312. (原始内容 (PDF)存档于2022-05-30) (德语).
- ^ C. Kaiser; T. Jen; E. Garvey; W.D. Bowen; D.F. Colella; J.R. Wardell Jr. Adrenergic agents. 4. Substituted phenoxypropanolamine derivatives as potential β-adrenergic agonists. Journal of Medicinal Chemistry. 1977, 20 (5): 687–689. PMID 16136. doi:10.1021/jm00215a014 (德语).
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