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肉桂腈

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肉桂腈
IUPAC名
3-Phenylprop-2-enenitrile
识别
CAS号 1885-38-7(反式)  checkY
24840-05-9(顺氏)  checkY
4360-47-8  checkY
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)[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
《全球化学品统一分类和标签制度》(简称“GHS”)中有毒物质的标签图案《全球化学品统一分类和标签制度》(简称“GHS”)中有害物质的标签图案
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丙烯腈碳酸钾存在下、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

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肉桂腈在催化下加氢,可以得到苯丙腈。[7]它和NMO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

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

参见

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