肉桂腈
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]
| 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 |
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| InChI |
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| 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）[1] |
| 熔点 | 22 °C（295 K）（反式）[2] −10 °C（263 K）（顺式）[3] |
| 沸点 | 263.8 °C（537.0 K）（反式）[2] |
| 危险性 | |
GHS危险性符号 
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| 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。 | |
反应 编辑
参考文献 编辑
- ^ 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.