肉桂腈

肉桂腈
	IUPAC名; 3-Phenylprop-2-enenitrile
識別
CAS號	1885-38-7（反式） ; 24840-05-9（順氏） ; 4360-47-8
PubChem	1550846
ChemSpider	1267328
SMILES	C(=C/C#N)\C1=CC=CC=C1;
InChI	1S/C9H7N/c10-8-4-7-9-5-2-1-3-6-9/h1-7H/b7-4+;
InChIKey	ZWKNLRXFUTWSOY-QPJJXVBHSA-N
EINECS	217-552-5
性質
化學式	C9H7N
摩爾質量	129.16 g·mol−1
密度	1.0374 g·cm−3 （15.2 °C，反式）
熔點	22 °C（295 K）（反式）; −10 °C（263 K）（順式）
沸點	263.8 °C（537.0 K）（反式）
危險性
	GHS危險性符號;
GHS提示詞	危險
H-術語	H301, H312, H317
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

肉桂腈是一種有機化合物，化學式為C₉H₇N。反式肉桂腈可由碘苯和丙烯腈在碳酸鉀存在下、乙酸鈀催化下反應得到，^[4]或由反式-β-溴苯乙烯和亞鐵氰酸鉀在鹼存在下、鈀配合物催化下反應得到；^[5]順式異構體則可由順式-β-溴苯乙烯在相同反應條件下反應得到。^[5]反式異構體在(–)-核黃素存在下於乙腈中光照（402 nm），也能轉化為順式異構體。^[6]

Quick Facts 肉桂腈, 識別 ...

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反應

肉桂腈在鈀催化下加氫，可以得到苯丙腈。^[7]它和NMO在四氧化鋨催化下反應，可以得到α,β-二羥基苯丙腈。^[8]

參考文獻

[1]
Houben, J.; Pfankuch, E. Imidolactones and salts of unsaturated nitriles. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen, 1926. 59B: 1594-1605.
[2]
"PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2022-06-25].
[3]
William H. Brown, George F. Wright. The Methoxymercurials from cis and trans Styryl Cyanide 1. Journal of the American Chemical Society. 1940-08, 62 (8): 1991–1994 [2022-06-25]. ISSN 0002-7863. doi:10.1021/ja01865a023. （原始內容存檔於2022-06-25）（英語）.
[4]
Vivek Srivastava. Carbene Based Palladium-catalyzed Mizoroki-Heck Reaction. Oriental Journal Of Chemistry. 2012-12-22, 28 (4): 1859–1863 [2022-06-25]. ISSN 0970-020X. doi:10.13005/ojc/280444. （原始內容存檔於2018-06-02）（英語）.
[5]
Oleg M. Nikitin, Olga V. Polyakova, Petr K. Sazonov, Alexander V. Yakimansky, Mikhail Ya. Goikhman, Irina V. Podeshvo, Tatiana V. Magdesieva. Polymer biquinolyl-containing complexes of Pd(II) as efficient catalysts for cyanation of aryl and vinyl halides with K₄Fe(CN)₆. New Journal of Chemistry. 2016, 40 (12): 10465–10473 [2022-06-25]. ISSN 1144-0546. doi:10.1039/C6NJ02345B （英語）.
[6]
Jan B. Metternich, Denis G. Artiukhin, Mareike C. Holland, Maximilian von Bremen-Kühne, Johannes Neugebauer, Ryan Gilmour. Photocatalytic E → Z Isomerization of Polarized Alkenes Inspired by the Visual Cycle: Mechanistic Dichotomy and Origin of Selectivity. The Journal of Organic Chemistry. 2017-10-06, 82 (19): 9955–9977 [2022-06-25]. ISSN 0022-3263. doi:10.1021/acs.joc.7b01281. （原始內容存檔於2022-06-25）（英語）.
[7]
Anuja Nagendiran, Henrik Sörensen, Magnus J. Johansson, Cheuk-Wai Tai, Jan-E. Bäckvall. Nanopalladium-catalyzed conjugate reduction of Michael acceptors – application in flow. Green Chemistry. 2016, 18 (9): 2632–2637 [2022-06-25]. ISSN 1463-9262. doi:10.1039/C5GC02920A （英語）.
[8]
Philippe Dupau, Robert Epple, Allen??A. Thomas, Valery??V. Fokin, K.??Barry Sharpless. Osmium-Catalyzed Dihydroxylation of Olefins in Acidic Media: Old Process, New Tricks. Advanced Synthesis & Catalyis. 2002-06, 344 (3-4): 421–433 [2022-06-25]. doi:10.1002/1615-4169(200206)344:3/43.0.CO;2-F.

參見

肉桂酸

[1] [1]
Houben, J.; Pfankuch, E. Imidolactones and salts of unsaturated nitriles. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen, 1926. 59B: 1594-1605.

[SRC-2] [2]
"PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2022-06-25].

[3] [3]
William H. Brown, George F. Wright. The Methoxymercurials from cis and trans Styryl Cyanide 1. Journal of the American Chemical Society. 1940-08, 62 (8): 1991–1994 [2022-06-25]. ISSN 0002-7863. doi:10.1021/ja01865a023. （原始內容存檔於2022-06-25）（英語）.

[4] [4]
Vivek Srivastava. Carbene Based Palladium-catalyzed Mizoroki-Heck Reaction. Oriental Journal Of Chemistry. 2012-12-22, 28 (4): 1859–1863 [2022-06-25]. ISSN 0970-020X. doi:10.13005/ojc/280444. （原始內容存檔於2018-06-02）（英語）.

[Oleg-5] [5]
Oleg M. Nikitin, Olga V. Polyakova, Petr K. Sazonov, Alexander V. Yakimansky, Mikhail Ya. Goikhman, Irina V. Podeshvo, Tatiana V. Magdesieva. Polymer biquinolyl-containing complexes of Pd(II) as efficient catalysts for cyanation of aryl and vinyl halides with K₄Fe(CN)₆. New Journal of Chemistry. 2016, 40 (12): 10465–10473 [2022-06-25]. ISSN 1144-0546. doi:10.1039/C6NJ02345B （英語）.

[6] [6]
Jan B. Metternich, Denis G. Artiukhin, Mareike C. Holland, Maximilian von Bremen-Kühne, Johannes Neugebauer, Ryan Gilmour. Photocatalytic E → Z Isomerization of Polarized Alkenes Inspired by the Visual Cycle: Mechanistic Dichotomy and Origin of Selectivity. The Journal of Organic Chemistry. 2017-10-06, 82 (19): 9955–9977 [2022-06-25]. ISSN 0022-3263. doi:10.1021/acs.joc.7b01281. （原始內容存檔於2022-06-25）（英語）.

[7] [7]
Anuja Nagendiran, Henrik Sörensen, Magnus J. Johansson, Cheuk-Wai Tai, Jan-E. Bäckvall. Nanopalladium-catalyzed conjugate reduction of Michael acceptors – application in flow. Green Chemistry. 2016, 18 (9): 2632–2637 [2022-06-25]. ISSN 1463-9262. doi:10.1039/C5GC02920A （英語）.

[8] [8]
Philippe Dupau, Robert Epple, Allen??A. Thomas, Valery??V. Fokin, K.??Barry Sharpless. Osmium-Catalyzed Dihydroxylation of Olefins in Acidic Media: Old Process, New Tricks. Advanced Synthesis & Catalyis. 2002-06, 344 (3-4): 421–433 [2022-06-25]. doi:10.1002/1615-4169(200206)344:3/43.0.CO;2-F.

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