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
別名	3-苯氧基丙烯; 烯丙氧基苯
識別
CAS號	1746-13-0
PubChem	74458
ChemSpider	21159535
SMILES	C=CCOc1ccccc1;
性質
化學式	C9H10O
摩爾質量	134.18 g·mol−1
外觀	無色固體
熔點	90 °C（363 K）
沸點	191.7 °C（464.8 K）
危險性
	GHS危險性符號;
GHS提示詞	警告
H-術語	H302, H312, H332
P-術語	P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P312, P322, P330, P363, P501
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

烯丙基苯基醚是一種有機化合物，化學式為C₆H₅OCH₂CH=CH₂。它在常溫常壓下是一種無色固體。

製備

烯丙基苯基醚是由苯酚鈉與烯丙基溴反應製備得來： ^[3]

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

當此反應在均勻乙二醇二甲醚溶液中進行時，產率幾乎是固定的。然而，當反應在的乙醚漿液形式進行時，主要產物則是酸處理後的2-烯丙基苯酚。

也有文獻報道以苯酚為原料，碳酸鉀為鹼，在碘化鉀的催化下和烯丙基氯在丙酮中回流反應製得。^[4]

反應

烯丙基苯基醚在酸催化劑存在下轉化為2-烯丙基苯酚。這種轉換是克萊森重排的一個例子。 ^[5] ^[6]

克萊森重排

在氯化鎳的催化下，使用硼氫化鈉對其加氫，可以得到正丙基苯基醚。^[7]它可以和三苯基矽烷（(C₆H₅)₃SiH）發生矽氫化反應，生成三苯基矽丙基苯基醚（(C₆H₅)₃Si(CH₂)₃OC₆H₅）。^[8]

參考資料

^ 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 （英語）.
^ 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 （英語）.

[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
別名	3-苯氧基丙烯烯丙氧基苯
識別
CAS號	1746-13-0 ^Y
PubChem	74458
ChemSpider	21159535
SMILES	C=CCOc1ccccc1
性質
化學式	C₉H₁₀O
摩爾質量	134.18 g·mol⁻¹
外觀	無色固體
熔點	90 °C（363 K）^[1]
沸點	191.7 °C（464.8 K）^[2]
危險性
GHS危險性符號
GHS提示詞	警告
H-術語	H302, H312, H332
P-術語	P261, P264, P270, P271, P280, P301+312, P302+352, P304+312, P304+340, P312, P322, P330, P363, P501
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。