| 词条 | 1,2-Benzoquinone |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477202978 | ImageFileL1 = Orthobenzoquinone.svg | ImageFileR1 = 1,2-benzoquinone-3D-vdW.png | PIN = Cyclohexa-3,5-diene-1,2-dione | OtherNames = 1,2-Benzoquinone (no longer recommended[1]) o-Benzoquinone (no longer recommended[1]) o-Quinone |Section1={{Chembox Identifiers | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C02351 | InChI = 1/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H | InChIKey = WOAHJDHKFWSLKE-UHFFFAOYAR | SMILES1 = C1=CC(=O)C(=O)C=C1 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C6H4O2/c7-5-3-1-2-4-6(5)8/h1-4H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = WOAHJDHKFWSLKE-UHFFFAOYSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 583-63-1 | PubChem = 11421 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = SVD1LJ47R7 | SMILES = O=C1/C=C\\C=C/C1=O | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 17253 | ChemSpiderID =10941 |Section2={{Chembox Properties | Formula = | C=6 | H=4 | O=2 | MolarMass = 108.0964 g/mol | Appearance = | Density = 1.424 g/cm3 | MeltingPt = | BoilingPtC = 213.3 | BoilingPt_notes = at 760 mmHg | Solubility = |Section7={{Chembox Hazards | MainHazards = | FlashPtC = 76.4 | AutoignitionPtC = |Section8={{Chembox Related | OtherCompounds = 1,4-benzoquinone quinone }} 1,2-Benzoquinone, also called ortho-benzoquinone, is an organic compound with formula {{chemical formula|C|6|H|4|O|2}}. It is one of the two isomers of quinone, the other being 1,4-benzoquinone. It is a red volatile solid that is soluble in water and ethyl ether. It is rarely encountered because of its instability, but it is of fundamental interest as the parent ortho-quinone, of which many analogues are known.[2] StructureThe molecule has C2v symmetry. X-ray crystallography shows that the double bonds are localized, with alternatingly long and short C-C distances within the ring. The C=O distances of 1.21 Å are characteristic of ketones.[3] Preparation and occurrence1,2-Benzoquinone is produced on oxidation of catechol exposed to air in aqueous solution[5] or by ortho oxidation of a phenol.[4] It is a precursor to melanin.[5] A strain of the bacterium Pseudomonas mendocina metabolises benzoic acid, yielding 1,2-benzoquinone via catechol.[6] References1. ^1 {{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 728 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}} {{DEFAULTSORT:Benzoquinone, 1,2-}}{{ketone-stub}}ベンゾキノン#1,2-ベンゾキノン2. ^Liao, Chun-Chen; Peddinti, Rama Krishna "Masked o-Benzoquinones in Organic Synthesis" Accounts of Chemical Research 2002, volume 35, pp. 856-866.{{DOI|10.1021/ar000194n}} 3. ^Macdonald, Alistair L.; Trotter, James "Crystal and molecular structure of o-benzoquinone" Journal of the Chemical Society, Perkin Transactions 2: 1973, pp. 476-80. {{DOI|10.1039/P29730000476}} 4. ^1 {{cite journal |author1=Magdziak, D. |author2=Rodriguez, A. A. |author3=Van De Water, R. W. |author4=Pettus, T. R. R. | title = Regioselective oxidation of phenols to o-quinones with o-iodoxybenzoic acid (IBX) | journal = Org. Lett. | volume = 4 | issue = 2 | pages = 285–288 | year = 2002 | doi = 10.1021/ol017068j | pmc = 1557836 | pmid=11796071}} 5. ^Enzymatic Browning in Fruits, Vegetables and Seafoods{{Dead link|date=November 2018 |bot=InternetArchiveBot |fix-attempted=yes }} Section 2.3.2 6. ^Chanda Parulekar and Suneela Mavinkurve (2006), Formation of ortho-benzoquinone from sodium benzoate by Pseudomonas mendocina | P=2 d. Indian Journal of Experimental Biology, volume 44, pages 157--162. 1 : 1,2-Benzoquinones |
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