| 词条 | 1,2,3-Triazole |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477202367 | ImageFileL1 = 1%2C2%2C3-triazole_numbering.png | ImageSizeL1 = 100px | ImageFileR1 = 1%2C2%2C3-Triazole3d.png | ImageSizeR1 = 100px | IUPACName = 1H-1,2,3-triazole | OtherNames = 1,2,3-triazole |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 35566 | ChemSpiderID = 60839 | InChI = 1/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5) | SMILES1 = c1cnn[nH]1 | InChIKey = QWENRTYMTSOGBR-UHFFFAOYAF | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = QWENRTYMTSOGBR-UHFFFAOYSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 288-36-8 | PubChem = | SMILES = C1=CN=NN1 }} |Section2={{Chembox Properties | Formula = C2H3N3 | MolarMass = 69.0654 | Appearance = colorless liquid | Density = 1.192 | MeltingPtC = 23 to 25 | MeltingPt_notes = | BoilingPtC = 203 | Solubility = very soluble | pKa = 9.4 | pKb = 1.2 }} |Section7={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} |Section8={{Chembox Related | OtherCompounds = 1,2,4-triazole imidazole }} }}1,2,3-Triazole is one of a pair of isomeric chemical compounds with molecular formula C2H3N3, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,3-Triazole is a basic aromatic heterocycle.[1] Substituted 1,2,3-triazoles can be produced using the azide alkyne Huisgen cycloaddition in which an azide and an alkyne undergo a 1,3-dipolar cycloaddition reaction. It is a surprisingly stable structure compared to other organic compounds with three adjacent nitrogen atoms. However, flash vacuum pyrolysis at 500 °C leads to loss of molecular nitrogen (N2) leaving a three-member aziridine ring. Certain triazoles are relatively easy to cleave due to ring-chain tautomerism. One manifestation is found in the Dimroth rearrangement. 1,2,3-Triazole finds use in research as a bioisostere in medicinal chemistry[2] building block for more complex chemical compounds, including pharmaceutical drugs such as mubritinib and tazobactam. The 2H-1,2,3-triazole tautomer is the major form in aqueous solution.[3] References1. ^{{cite book | title=Heterocyclic chemistry | first1= T.L. | last1=Gilchrist | publisher=Prentice Hall Press | year=1987 |isbn=0-582-01421-2}} {{DEFAULTSORT:Triazole, 1, 2, 3-}}2. ^{{cite journal|authors=Bonandi, E.; Christodoulou, M. S.; Fumagalli, G.; Perdicchia, D.; Rastelli, G.; Passarella, D.|title=The 1,2,3-triazole ring as a bioisostere in medicinal chemistry|journal=Drug Discov Today|year=2017|volume=22|issue=10|pages=1572–1581 |pmid=28676407 |doi=10.1016/j.drudis.2017.05.014}} 3. ^{{cite journal | first1= Adrien | last1=Albert | first2= Peter J. | last2=Taylor | title=The tautomerism of 1,2,3-triazole in aqueous solution | journal=Journal of the Chemical Society, Perkin Transactions 2 | issue=11 | pages=1903-1905 | year=1989 | doi=10.1039/P29890001903}} 1 : Triazoles |
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