| 词条 | Norbornene |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 450599059 | Reference = [1] | ImageFileL1 = Norbornene.png | ImageFileR1 = Norbornene2.png | ImageFile2 = Norbornene3.png | ImageSize2 = 150px | PIN = Bicyclo[2.2.1]hept-2-ene | OtherNames = Norbornylene Norcamphene |Section1={{Chembox Identifiers | Abbreviations = | PubChem = 10352 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 9925 | InChI = 1/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2 | InChIKey = JFNLZVQOOSMTJK-UHFFFAOYAB | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = JFNLZVQOOSMTJK-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 498-66-8 | EINECS = 207-866-0 | SMILES = C1=CC2CCC1C2 | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = }} |Section2={{Chembox Properties | C=7 | H=10 | Appearance = White solid | Density = | MeltingPtC = 42 to 46 | BoilingPtC = 96 | BoilingPt_notes = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = |Section7={{Chembox Hazards | EUClass = | MainHazards = | NFPA-H = 2 | NFPA-F = 3 | NFPA-R = 1 | NFPA-S = | RPhrases = | SPhrases = | RSPhrases = | FlashPtC = −15 | AutoignitionPtC = | ExploLimits = | PEL = }} Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon. It is a white solid with a pungent sour odor. The molecule consists of a cyclohexene ring with a methylene bridge between carbons 1 and 4. The molecule carries a double bond which induces significant ring strain and significant reactivity. ProductionNorbornene is made by a Diels–Alder reaction of cyclopentadiene and ethylene. Many substituted norbornenes can be prepared similarly.[2][3] Related bicyclic compounds are norbornadiene, which has the same carbon skeleton but with two double bonds, and norbornane which is prepared by hydrogenation of norbornene. ReactionsNorbornene undergoes an acid-catalyzed hydration reaction to form norborneol. This reaction was of great interest in the elucidation of the non-classical carbonion controversy. Norbornene is used in the Catellani reaction and in norbornene-mediated meta-C−H activation.[4] Certain substituted norbornenes undergo unusual substitution reactions owing to the generation of the 2-norbornyl cation. PolynorbornenesNorbornenes are important monomers in ring-opening metathesis polymerizations (ROMP). Typically these conversions are effected with ill-defined catalysts. Polynorbornenes exhibit high glass transition temperatures and high optical clarity.[5] In addition to ROMP, norbornene monomers also undergo vinyl-addition polymerization. Polynorbornene is used mainly in the rubber industry for anti-vibration (rail, building, industry), anti-impact (personal protective equipment, shoe parts, bumpers) and grip improvement (toy tires, racing tires, transmission systems, transports systems for copiers, feeders, etc.) Ethylidene norbornene is a related monomer derived from cyclopentadiene and butadiene. References1. ^[https://fscimage.fishersci.com/msds/66955.htm Norbornene MSDS] 2. ^{{OrgSynth | first1= Paul |last1=Binger |first2=Petra |last2=Wedemann |first3=Udo H. |last3=Brinker| title = Cyclopropene: A New Simple Synthesis and its Diels-Alder Reaction with Cyclopentadiene | collvol = 10 | collvolpages = 231 | prep=v77p0254}} 3. ^{{OrgSynth | first1=Masaji |last1=Oda |first2=Takeshi |last2=Kawase |first3=Tomoaki |last3=Okada |first4=Tetsuya |last4=Enomoto | title = 2-Cyclohexene-1,4-dione | collvol = 9 | collvolpages = 186 | prep = cv9p0186}} 4. ^{{cite journal|last=Thansandote|first=Praew|date=21 May 2010|title=Palladium-Catalyzed Domino C−C/C−N Coupling Using a Norbornene Template: Synthesis of Substituted Benzomorpholines, Phenoxazines, and Dihydrodibenzoxazepines|journal=The Journal of Organic Chemistry|volume=75|issue=10|pages=3495–3498|doi=10.1021/jo100408p|pmid=20423091|last2=Chong|first2=Eugene|last3=Feldmann|first3=Kai-Oliver|last4=Lautens|first4=Mark}} 5. ^{{cite encyclopedia|encyclopedia=Kirk-Othmer Encyclopedia of Chemical Technology|first1=Lionel |last1=Delaude |first2=Alfred F. |last2=Noels|year=2005| doi=10.1002/0471238961.metanoel.a01|place=Weinheim|publisher=Wiley-VCH|isbn = 978-0471238966|chapter = Metathesis}} 3 : Monomers|Cyclopentenes|Cyclopentanes |
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