| 词条 | 2-Acetylfuran |
| 释义 |
| ImageFile = 2-Acetylfuran.svg | ImageSize = 150px | PIN = 1-(Furan-2-yl)ethan-1-one | OtherNames = 1-(Furan-2-yl)ethanone 1-(2-Furanyl)-ethanone 2-Acetylfuran Acetyl furan 2-Furyl methyl ketone |Section1={{Chembox Identifiers | CASNo = 1192-62-7 | PubChem = 14505 | ChemSpiderID = 13849 | ChEBI = 59983 | SMILES = CC(=O)C1=CC=CO1 | InChI = 1/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3 | InChIKey = IEMMBWWQXVXBEU-UHFFFAOYAG | StdInChI = 1S/C6H6O2/c1-5(7)6-3-2-4-8-6/h2-4H,1H3 | StdInChIKey = IEMMBWWQXVXBEU-UHFFFAOYSA-N |Section2={{Chembox Properties | C=6 | H=6 | O=2 | Appearance = Low melting solid | Density = 1.0975 at 20 °C | MeltingPtC = 30 | BoilingPtC = 168 to 169 | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}2-Acetylfuran is a low melting solid or high boiling liquid, depending on temperature.[1][2] The solid melts at 30 °C and has a density of 1.0975 g/ml at 20 °C, while the normal boiling point of the liquid is 168–169 °C.[3] 2-Acetylfuran is a useful intermediate in the synthesis of fine chemicals and pharmaceuticals, and is used in the production of the generic cephalophosphorin antibiotic cefuroxime.[4] Synthesis2-Acetylfuran was prepared by Ashina in 1914 via the reaction of the methyl Grignard reagent on 2-furonitrile.[5] Modern industrial synthesis generally involves the Friedel–Crafts acylation of furan with acetic anhydride. ApplicationsPharmaceuticalsA one-pot synthesis of an intermediate to the HIV integrase inhibitor S-1360 was based on the Friedel-Crafts alkylation of 2-acetylfuran with 4-fluorobenzyl chloride using zinc chloride catalyst.[6] Reaction of 2-acetylfuran with aqueous sodium nitrite gave 2-furanyloxoacetic acid, an intermediate to Cefuroxime, a second-generation cephalosporin antibiotic.[7] See also
References1. ^{{cite journal | author = Howard D. Hartough| title = Acylation of thiophene and furan by means of boron trifluoride. VII| journal = Journal of the American Chemical Society| volume = 70 | pages = 867| year = 1948| last2 = Kosak| first2 = Alvin I.|doi=10.1021/ja01182a510 }} {{DEFAULTSORT:Acetylfuran, 2-}}2. ^{{cite journal | author = Walther Borsche| title = Cleavage of the furan ring by primary aromatic amines and hydrochloric acid| journal = Berichte der Deutschen Chemischen Gesellschaft B| volume = 71| pages = 957–66| year = 1938| last2 = Leditschke| first2 = Heinrich| last3 = Lange| first3 = Karl}} 3. ^{{cite journal | author = Y. Asahina| title = Ethereal oil of Elsholtzia cristata Willdenow (Lablatae)| journal = Archiv der Pharmazie| volume = 252| pages =435–48| year = 1914| last2 = Murayama| first2 = Y.| doi=10.1002/ardp.19142520609}} 4. ^{{cite journal | author = Rong-geng Wang| title = Side chain of cefuroxime: (Z)-2-methoxyimino-2-(fury-2-yl)acetic acid ammonium salt| journal = Jingxi Yu Zhuanyong Huaxuepin| volume = 12 | issue = 17| pages = 10–11| year = 2004| last2 = Liu| first2 = Cheng-ping| last3 = Zhu| first3 = Kun-peng| last4 = Du| first4 = Hai-lin | last5 = Liu| first5 = Lie-yi }} 5. ^{{cite journal | first1 = Y. |last1 = Asahina| title = Ethereal oil of Elsholtzia cristata Willdenow (Lablatae)| journal = Archiv der Pharmazie| volume = 252| pages =435–48| year = 1914| last2 = Murayama| first2 = Y.| doi=10.1002/ardp.19142520609}} 6. ^{{cite journal | author = Kenji Izumi| title = One-Step Synthesis of 5-(4-Fluorobenzyl)-2-furyl Methyl Ketone: A Key Intermediate of HIV-Integrase Inhibitor S-1360| journal = Organic Process Research & Development| volume = 11 | issue = 6| pages = 1059–1061| year = 2007| last2 = Kabaki| first2 = Mikio| last3 = Uenaka| first3 = Masaaki| last4 = Shimizu| first4 = Sumio| doi=10.1021/op700117q}} 7. ^{{cite journal | author = Rui-min Lv| title = The research for the synthesis of 2-methoxyimino-2-furylacetic acid| journal = Shandong Huagong| volume = 34 | issue = 6| pages = 5–8| year = 2005| last2 = Zhang| first2 = Zhi-de| last3 = Zhang| first3 = Zhi-cheng}} 1 : Furans |
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