肉桂腈

肉桂腈
	IUPAC名; 3-Phenylprop-2-enenitrile
识别
CAS号	1885-38-7（反式） ; 24840-05-9（顺氏） ; 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
性质
化学式	C9H7N
摩尔质量	129.16 g·mol−1
密度	1.0374 g·cm−3 （15.2 °C，反式）
熔点	22 °C（295 K）（反式）; −10 °C（263 K）（顺式）
沸点	263.8 °C（537.0 K）（反式）
危险性
	GHS危险性符号;
GHS提示词	危险
H-术语	H301, H312, H317
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

肉桂腈是一种有机化合物，化学式为C₉H₇N。反式肉桂腈可由碘苯和丙烯腈在碳酸钾存在下、乙酸钯催化下反应得到，^[4]或由反式-β-溴苯乙烯和亚铁氰酸钾在碱存在下、钯配合物催化下反应得到；^[5]顺式异构体则可由顺式-β-溴苯乙烯在相同反应条件下反应得到。^[5]反式异构体在(–)-核黄素存在下于乙腈中光照（402 nm），也能转化为顺式异构体。^[6]

反应

肉桂腈在钯催化下加氢，可以得到苯丙腈。^[7]它和NMO在四氧化锇催化下反应，可以得到α,β-二羟基苯丙腈。^[8]

参考文献

^ Houben, J.; Pfankuch, E. Imidolactones and salts of unsaturated nitriles. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen, 1926. 59B: 1594-1605.
^ ^2.0 ^2.1 "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US). Retrieved from SciFinder. [2022-06-25].
^ 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. （原始内容存档于2022-06-25）（英语）.
^ 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. （原始内容存档于2018-06-02）（英语）.
^ ^5.0 ^5.1 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 （英语）.
^ 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. （原始内容存档于2022-06-25）（英语）.
^ 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 （英语）.
^ 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.

参见

肉桂酸

[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] 2.0 ^2.1 "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. （原始内容存档于2022-06-25）（英语）.

[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. （原始内容存档于2018-06-02）（英语）.

[Oleg-5] 5.0 ^5.1 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 （英语）.

[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. （原始内容存档于2022-06-25）（英语）.

[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 （英语）.

[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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