烯丙基苯基醚

烯丙基苯基醚
	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	C=CCOc1ccccc1;
性质
化学式	C9H10O
摩尔质量	134.18 g·mol−1
外观	无色固体
熔点	90 °C（363 K）
沸点	191.7 °C（464.8 K）
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，化学式为C₆H₅OCH₂CH=CH₂。它在常温常压下是一种无色固体。

制备

烯丙基苯基醚是由苯酚钠与烯丙基溴反应制备得来： ^[3]

{\ce {C6H5ONa + BrCH2CH=CH2 ->C6H5OCH2CH=CH2 + NaBr}}

当此反应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，当反应在的乙醚浆液形式进行时，主要产物则是酸处理后的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

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

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]

参考资料

^ 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.

[1] Derivative of p-aminophenol applicable therapeutically. 1918. CH 76619. CAN12: 8271.

[2] "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2021-07-15].

[3] 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.

[4] 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.

[5] Martín Castro, Ana M. Claisen Rearrangement over the Past Nine Decades. Chemical Reviews. 2004, 104 (6): 2939–3002. PMID 15186185. doi:10.1021/cr020703u.

[6] 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

[7] 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）.

[8] 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.

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烯丙基苯基醚

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 ^Y
PubChem	74458
ChemSpider	21159535
SMILES	C=CCOc1ccccc1
性质
化学式	C₉H₁₀O
摩尔质量	134.18 g·mol⁻¹
外观	无色固体
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。