| 词条 | Acetonedicarboxylic acid |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477239490 | Reference = [1] | ImageFile = Acetonedicarboxylic acid.png | ImageSize = 180px | ImageName = Skeletal formula | ImageFile1 = Acetonedicarboxylic-acid-3D-balls.png | ImageSize1 = 210px | ImageName1 = Ball-and-stick model | PIN = 3-Oxopentanedioic acid | OtherNames = {{unbulleted list|1,3-Acetonedicarboxylic acid| 3-oxoglutaric acid| 3-ketoglutaric acid| β-ketoglutaric acid}} |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 61623 | InChI1 = 1/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10) | InChIKey1 = OXTNCQMOKLOUAM-UHFFFAOYAR | SMILES1 = O=C(O)CC(=O)CC(=O)O | CASNo_Ref = {{cascite|changed|??}} | CASNo =542-05-2 | PubChem =68328 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C5H6O5/c6-3(1-4(7)8)2-5(9)10/h1-2H2,(H,7,8)(H,9,10) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = OXTNCQMOKLOUAM-UHFFFAOYSA-N | SMILES =C(C(=O)CC(=O)O)C(=O)O | EINECS = 208-797-9 |Section2={{Chembox Properties | C=5 | H=6 | O=5 | MolarMass =146.09814 g/mol | Appearance = | Density =1.499 g/cm3 | MeltingPtC = 122 | MeltingPt_notes = (decomposes) | MeltingPt_ref = | BoilingPtC = 408.4 | BoilingPt_notes =(760mm Hg) | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPtC = 214.9 | AutoignitionPtC = }} Acetonedicarboxylic acid, 3-oxoglutaric acid or β-ketoglutaric acid is a simple dicarboxylic acid. PreparationIt is commercially available but may also be prepared by decarboxylation of citric acid in fuming sulfuric acid:[2] ApplicationsAcetonedicarboxylic acid and its derivatives are primarily used as building blocks in organic chemistry, particularly in the synthesis of heterocyclic rings[3] and in the Weiss–Cook reaction. Acetonedicarboxylic acid is well-known to be used in the Robinson tropinone synthesis. Acetonedicarboxylic acid also finds use in the synthesis of Timcodar & dezaguanine (3-deazaguanine, 3-DG). Diethyl 1,3-acetonedicarboxylate saw use in the synthesis of Zomepirac. The presence of β-ketoglutaric acid in human urine can be used as a diagnostic test for the overgrowth of harmful gut flora such as Candida albicans.[4] See also
References1. ^1,3-Acetonedicarboxylic acid{{dead link|date=October 2016 |bot=InternetArchiveBot |fix-attempted=yes }} at Sigma-Aldrich (safety data sheet) 2. ^{{OrgSynth | author = Roger Adams |author2=H. M. Chiles |author3=C. F. Rassweiler | title = Acetonedicarboxylic Acid | collvol = 1 | collvolpages = 10 | year = 1941 | prep = cv1p0010}} 3. ^{{Cite journal | last1 = Stanovnik | first1 = Branko | last2 = Grošelj | first2 = Uroš| year = 2010 | title = CHAPTER 5 – Dialkyl Acetone-1,3-Dicarboxylates and their Mono- and bis(Dimethylamino)methylidene Derivatives in the Synthesis of Heterocyclic Systems | journal = Advances in Heterocyclic Chemistry | volume = 100 | pages = 145–174 | doi = 10.1016/S0065-2725(10)10005-1| series = Advances in Heterocyclic Chemistry | isbn = 9780123809360 }} 4. ^Schmidt, Michael A, Tired of Being Tired: Overcoming Chronic Fatigue and Low Energy 3 : Ketones|Dicarboxylic acids|Keto acids |
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