| 词条 | 1,4-Naphthoquinone |
| 释义 |
| Verifiedfields = changed | verifiedrevid = 414651852 | Reference =[1] | Name = Naphthoquinone | ImageFile = 1,4-Naphthoquinone.svg | ImageSize = 130 | ImageFile1 = 1,4-Naphthoquinone-3D-balls.png | ImageSize1 = 180 | ImageName1 = Ball-and-stick model | PIN = Naphthalene-1,4-dione | OtherNames = 1,4-Naphthoquinone Naphthoquinone α-Naphthoquinone |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 130-15-4 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 55934 | PubChem = 8530 | ChemSpiderID = 8215 | InChI = 1/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H | InChIKey = FRASJONUBLZVQX-UHFFFAOYAK | StdInChI = 1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H | StdInChIKey = FRASJONUBLZVQX-UHFFFAOYSA-N | SMILES = O=C2C=CC(C1=CC=CC=C12)=O |Section2={{Chembox Properties | Formula = C{{sub|10}}H{{sub|6}}O{{sub|2}} | MolarMass = 158.15 g/mol | Density = 1.422 g/cm{{sup|3}} | MeltingPtC = 126 | MeltingPt_notes = | BoilingPt = Begins to sublime at 100 °C | Solubility = 0.09 g/L | MagSus = -73.5·10{{sup|−6}} cm{{sup|3}}/mol }} 1,4-Naphthoquinone or para-naphthoquinone is an organic compound derived from naphthalene. It forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. It is almost insoluble in cold water, slightly soluble in petroleum ether, and more soluble in polar organic solvents. In alkaline solutions it produces a reddish-brown color. Vitamin K is a derivative of 1,4-naphthoquinone. It is a planar molecule with one aromatic ring fused to a quinone subunit.[2] It is an isomer of 1,2-naphthoquinone. PreparationThe industrial synthesis involves aerobic oxidation of naphthalene over a vanadium oxide catalyst:[3] C{{sub|10}}H{{sub|8}} + 3/2 O{{sub|2}} → C{{sub|10}}H{{sub|6}}O{{sub|2}} + H{{sub|2}}O In the laboratory, naphthoquinone can be produced by the oxidation of a variety of naphthalene compounds. An inexpensive route involves oxidation of naphthalene with chromium trioxide.[4] Reactions1,4-Naphthoquinone acts as strong dienophile in Diels-Alder reaction. Its adduct with 1,3-butadiene can be prepared by two methods: 1) long (45 days) exposure of naphthoquinone in neat liquid butadiene taken in huge excess at room temperature in a thick-wall glass tube or 2) fast catalyzed cycloaddition at low temperature in the presence of 1 equivalent of tin(IV) chloride:[5] Uses1,4-Naphthoquinone is mainly used as a precursor to anthraquinone by reaction with butadiene followed by oxidation. Nitration gives 5-nitro-1,4-naphthalenedione, precursor to an {{Not a typo|aminoanthroquinone}} that is used as a dye precursor.[3] DerivativesNaphthoquinone forms the central chemical structure of many natural compounds, most notably the K vitamins. 2-Methyl-1,4-naphthoquinone, called menadione, is a more effective coagulant than vitamin K. Other natural naphtoquinones include juglone, plumbagin, droserone. Naphthoquinone derivatives have significant pharmacological properties. They are cytotoxic, they have significant antibacterial, antifungal, antiviral, insecticidal, anti-inflammatory, and antipyretic properties. Plants with naphthoquinone content are widely used in China and the countries of South America, where they are used to treat malignant and parasitic diseases.[6] Naphthoquinone functions as a ligand through its electrophilic carbon-carbon double bonds.[7] Dichlone, a chlorinated derivative of 1,4-naphthoquinone, is used as a fungicide. See also
References1. ^Merck Index, 11th Edition, 6315. {{Vitamin}}{{Natural phenol}}{{DEFAULTSORT:Naphthoquinone, 1, 4-}}2. ^{{ cite journal |author1=Gaultier, J. |author2=Hauw, C. | title = Structure de l'α-Naphtoquinone | journal = Acta Crystallographica | year = 1965 | volume = 18 | issue = 2 | pages = 179–183 | doi = 10.1107/S0365110X65000439 }} 3. ^1 {{ Ullmann | author = Grolig, J. | author2 = Wagner, R. | title = Naphthoquinones | doi = 10.1002/14356007.a17_067 }} 4. ^{{ OrgSynth | author = Braude, E. A. | author2 = Fawcett, J. S. | year = 1953 | title = 1,4-Naphthoquinone | volume = 33 | pages = 50 | collvol = 4 | collvolpages = 698 | prep = CV4P0698 | url = http://www.orgsyn.org/orgsyn/pdfs/CV4P0698.pdf }} 5. ^{{ cite journal | author = M.A. Filatov | author2 = S. Baluschev | author3 = I.Z. Ilieva| author4 = V. Enkelmann | author5 = T. Miteva| author6 = K. Landfester | author7 = S.E. Aleshchenkov | author8 = A.V. Cheprakov | title = Tetraaryltetraanthra[2,3]porphyrins: Synthesis, Structure, and Optical Properties | journal = J. Org. Chem. | year = 2012 | volume = 77 | issue = 24 | pages = 11119–11131 | doi = 10.1021/jo302135q }} 6. ^{{ cite journal | last1 = Babula | first1 = P. | last2 = Adam | first2 = V. | last3 = Havel | first3 = L. | last4 = Kizek | first4 = R. |title = Naphthoquinones and their Pharmacological Properties | language = Czech | journal = Ceská a Slovenská Farmacie | year = 2007 | volume = 56 | issue = 3 | pages = 114–120 | pmid = 17867522 }} 7. ^{{ cite journal |author1=Kündig, E. P. |author2=Lomberget, T. |author3=Bragg, R. |author4=Poulard, C. |author5=Bernardinelli, G. | title = Desymmetrization of a meso-Diol Complex Derived from [Cr(CO){{sub|3}}(η{{sup|6}}-5,8-Naphthoquinone)]: Use of New Diamine Acylation Catalysts | journal = Chemical Communications | year = 2004 | volume = 2004 | issue = 13 | pages = 1548–1549 | doi = 10.1039/b404006f }} 1 : 1,4-Naphthoquinones |
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