查看“︁烯丙基苯基醚”︁的源代码

{{Chembox
|ImageFile=Allyl phenyl ether.svg|ImageSize=200px|PIN=[(Prop-2-en-1-yl)oxy]benzene|OtherNames=3-苯氧基丙烯<br>烯丙氧基苯
|Section1={{Chembox Identifiers
| CASNo = 1746-13-0
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 74458
| ChemSpiderID = 21159535
| EC_number = 217-125-3
| UNII = 26S07OSX4O
| SMILES = C=CCOc1ccccc1
| StdInChI=1S/C9H10O/c1-2-8-10-9-6-4-3-5-7-9/h2-7H,1,8H2 COPY
| StdInChIKey = POSICDHOUBKJKP-UHFFFAOYSA-N
 }}|Section2={{Chembox Properties
| C=9|H=10|O=1
| Appearance = 無色固體
| Density = 
| MeltingPt = {{convert|90|C|K}}<ref>Derivative of p-aminophenol applicable therapeutically. 1918. CH 76619. CAN12: 8271.</ref>
| BoilingPt = {{convert|191.7|C|K}}<ref>"PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2021-07-15].</ref>
| Solubility = }}|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = 警告
| HPhrases = {{H-phrases|302|312|332}}
| PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+312|304+340|312|322|330|363|501}}
 }}|IUPAC中=[(丙-2-烯-1-基)氧]苯}}
'''烯丙基苯基醚'''是一种[[有机化合物]]，化學式为C<sub>6</sub>H<sub>5</sub>OCH<sub>2</sub>CH=CH<sub>2</sub>。它在常溫常壓下是一种无色固体。

== 製備 ==
烯丙基苯基醚是由[[苯酚钠]]与[[烯丙基溴]]反应製備得來： <ref>{{Cite journal|title=Heterogeneity as a Factor in the Alkylation of Ambident Anions: Phenoxide Ions1,2|last=Kornblum|first=Nathan|last2=Lurie|first2=Arnold P.|journal=Journal of the American Chemical Society|issue=11|doi=10.1021/ja01520a030|year=1959|volume=81|pages=2705–2715}}</ref>

: <chem>C6H5ONa + BrCH2CH=CH2 ->C6H5OCH2CH=CH2 + NaBr</chem>

當此反應在均匀[[乙二醇二甲醚]]溶液中进行时，产率几乎是固定的。然而，當反应在的[[乙醚]]浆液形式进行时，主要产物則是酸处理后的[[2-烯丙基苯酚]]。

也有文献报道以[[苯酚]]为原料，[[碳酸钾]]为碱，在[[碘化钾]]的催化下和[[烯丙基氯]]在[[丙酮]]中回流反应制得。<ref>{{cite journal|last1=Hoang|first1=Giang T.|last2=Walsh|first2=Dylan J.|last3=McGarry|first3=Kathryn A.|last4=Anderson|first4=Constance B.|last5=Douglas|first5=Christopher J.|title=Development and Mechanistic Study of Quinoline-Directed Acyl C–O Bond Activation and Alkene Oxyacylation Reactions|journal=The Journal of Organic Chemistry|volume=82|issue=6|year=2017|pages=2972–2983|issn=0022-3263|doi=10.1021/acs.joc.6b03011}}</ref>
== 反应 ==
烯丙基苯基醚在酸催化剂存在下转化为[[2-烯丙基苯酚]]。这种转换是[[克莱森重排反应|克莱森重排]]的一个例子。 <ref>{{Cite journal|title=Claisen Rearrangement over the Past Nine Decades|last=Martín Castro|first=Ana M.|journal=Chemical Reviews|issue=6|doi=10.1021/cr020703u|year=2004|volume=104|pages=2939–3002|pmid=15186185}}</ref> <ref>Yadav, G. D.; Lande, S. V., UDCaT-5: A Novel and Efficient Solid Superacid Catalyst for Claisen Rearrangement of Substituted Allyl Phenyl Ethers. Synthetic Communications 2007, 37 (6), 941-946</ref>
[[File:Aromatic Claisen 1.svg|居中|300px|克莱森重排]]
在[[氯化镍]]的催化下，使用[[硼氢化钠]]对其加氢，可以得到正丙基苯基醚<!-- CAS：622-85-5 -->。<ref>{{cite journal|journal=RSC Advances|volume=8|issue=14|language=en|issn=2046-2069|date=2018|pages=7761–7764|doi=10.1039/C8RA00905H|url=http://xlink.rsc.org/?DOI=C8RA00905H|title=Sodium borohydride-nickel chloride hexahydrate in EtOH/PEG-400 as an efficient and recyclable catalytic system for the reduction of alkenes|accessdate=2021-07-15|author=Kaoxue Li, Chuanchao Liu, Kang Wang, Yang Ren, Fahui Li}}</ref>它可以和[[三苯基硅烷]]（(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>SiH）发生硅氢化反应，生成三苯基硅丙基苯基醚（(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>Si(CH<sub>2</sub>)<sub>3</sub>OC<sub>6</sub>H<sub>5</sub>）。<ref>{{cite journal|last1=Żak|first1=P.|last2=Bołt|first2=M.|last3=Kubicki|first3=M.|last4=Pietraszuk|first4=C.|title=Highly selective hydrosilylation of olefins and acetylenes by platinum(0) complexes bearing bulky N-heterocyclic carbene ligands|journal=Dalton Transactions|volume=47|issue=6|year=2018|pages=1903–1910|issn=1477-9226|doi=10.1039/C7DT04392A}}</ref>

== 参考資料 ==
{{Reflist}}

[[Category:烯丙基化合物]]
[[Category:苯醚]]