2-氰基-3-苯基丙烯酸乙酯

化合物

2-氰基-3-苯基丙烯酸乙酯是一种有机化合物,化学式为C12H11NO2

2-氰基-3-苯基丙烯酸乙酯
识别
CAS号 2025-40-3  checkY
2169-69-9E checkY
14533-87-0Z checkY
性质
化学式 C12H11NO2
摩尔质量 201.22 g·mol−1
熔点 50—51 °C(323—324 K)[1][2]
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

合成与反应

2-氰基-3-苯基丙烯酸乙酯可由苯甲醛氰乙酸乙酯乙醇反应得到,该反应的动力学研究表明,在氨丙基功能化二氧化硅(APS)催化时,苯甲醛零级,氰乙酸乙酯为一级[3]

它和次氯酸钠反应,可以得到环氧化物(2-氰基-3-苯基环氧丙酸乙酯)。[4]它在催化下加氢,可以得到α-氰基苯丙酸乙酯[5];在氯化钴催化下,它可以被硼氢化钠还原为α-羟甲基苯丙腈。[6]

参考文献

  1. ^ Ming Zhang, Ai-Qin Zhang, Zhi-Hong Deng. Two mild methods for synthesis of α,β–unsaturated cyanoesters. Journal of Chemical Research. 2005-01, 2005 (1): 69–70 [2023-02-22]. ISSN 1747-5198. doi:10.3184/0308234053431185. (原始内容存档于2023-02-22) (英语). 
  2. ^ Majid M. Heravi, Maryam H. Tehrani, Khadijeh Bakhtiari, Hossein A. Oskooie. A Practical Knoevenagel Condensation Catalysed by Imidazole. Journal of Chemical Research. 2006-09, 2006 (9): 561–562 [2023-02-22]. ISSN 1747-5198. doi:10.3184/030823406778521329. (原始内容存档于2023-02-22) (英语). 
  3. ^ Christian P. Haas, Tibor Müllner, Richard Kohns, Dirk Enke, Ulrich Tallarek. High-performance monoliths in heterogeneous catalysis with single-phase liquid flow. Reaction Chemistry & Engineering. 2017, 2 (4): 498–511 [2023-02-22]. ISSN 2058-9883. doi:10.1039/C7RE00042A (英语). 
  4. ^ Sara Meninno, Luca Zullo, Jacob Overgaard, Alessandra Lattanzi. Tunable Cinchona -Based Thioureas-Catalysed Asymmetric Epoxidation to Synthetically Important Glycidic Ester Derivatives. Advanced Synthesis & Catalysis. 2017-03-20, 359 (6): 913–918 [2023-02-22]. doi:10.1002/adsc.201700146. (原始内容存档于2023-02-21) (英语). 
  5. ^ Ken Motokura, Noriaki Fujita, Kohsuke Mori, Tomoo Mizugaki, Kohki Ebitani, Koichiro Jitsukawa, Kiyotomi Kaneda. Environmentally Friendly One-Pot Synthesis of α-Alkylated Nitriles Using Hydrotalcite-Supported Metal Species as Multifunctional Solid Catalysts. Chemistry - A European Journal. 2006-11-06, 12 (32): 8228–8239 [2023-02-22]. doi:10.1002/chem.200600317 (英语). 
  6. ^ Arun Jagdale, Abhimanyu Paraskar, Arumugam Sudalai. Cobalt(II) Chloride Hexahydrate-Diisopropylamine Catalyzed Mild and Chemoselective Reduction of Carboxylic Esters with Sodium Borohydride. Synthesis. 2009-02, 2009 (04): 660–664 [2023-02-22]. ISSN 0039-7881. doi:10.1055/s-0028-1083353. (原始内容存档于2018-06-03) (英语).