ethyl 2-cyano-5-oxo-3-phenyl-5-p-tolylpentanoate | 135885-87-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: ethyl 2-cyano-5-oxo-3-phenyl-5-p-tolylpentanoate
• 英文别名: Ethyl 2-cyano-5-(4-methylphenyl)-5-oxo-3-phenylpentanoate；ethyl 2-cyano-5-(4-methylphenyl)-5-oxo-3-phenylpentanoate
• CAS: 135885-87-9
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: VMBQILNYWJKUJA-UHFFFAOYSA-N

物化性质

• 沸点：
  523.9±50.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyano-5-oxo-3-phenyl-5-p-tolylpentanoate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 1-(4-甲基苯基)-3-苯基丙-2-烯-1-酮
  参考文献：
  名称：

  Darwish, A. I., Egyptian Journal of Chemistry, 2002, vol. 45, # 4, p. 695 - 711

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(4-甲基苯基)-3-苯基丙-2-烯-1-酮 、 氰乙酸乙酯 在 Thermomyces lanuginosus lipase immobilized on the surface of Fe₃O₄/ZnO core/shell magnetic nanoparticles 作用下， 以 异辛烷 为溶剂， 反应 1.0h， 以79%的产率得到ethyl 2-cyano-5-oxo-3-phenyl-5-p-tolylpentanoate
  参考文献：
  名称：

  Immobilization of lipase on Fe3O4/ZnO core/shell magnetic nanoparticles and catalysis of Michael-type addition to chalcone derivatives

  摘要：

  Fe3O4/ZnO core/shell magnetic nanoparticles in 1:1 and 1:2 molar ratios were prepared and characterized by using X-ray powder diffraction, scanning electron microscopy, thermogravimetric analysis, FT-IR spectra, and flame atomic absorption spectrophotometry. Thermomyces lanuginosa lipase (TLL) was then covalently immobilized on the surface of both supports. An immobilization efficiency and yield of 94 +/- 2.5% and 86 +/- 3.5%, respectively, were measured for nanoparticles in 1:1 molar ratio of Fe3O4/ZnO and immobilization efficiency and yield were 89 +/- 2.2% and 81 +/- 3.1%, respectively, when lipase was bound to the functionalized nanoparticles in 1:2 molar ratio. The obtained result indicated that the immobilization considerably improved thermal, pH, and operational stability of TLL compared to the soluble enzyme. Moreover, the immobilized enzyme and seven other commercially lipases were examined for Micheal addition of active methylene compounds to chalcones. TLL resulted in the highest yield of the related reaction product compared to other enzymes. For further optimization of Micheal reaction conditions, the effect of some organic solvents was also examined and the obtained results revealed that hydrophobic solvents were more suitable than others. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.12.006

文献信息

• A mild, chemoselective, one-pot synthesis of δ-keto α-cyano esters by organocatalysis
  作者：Gang Liu、Yingcai Wang

  DOI：10.1016/j.tetlet.2013.10.145

  日期：2014.1

  A sequential condensation of α-cyano esters, aldehydes, and ketones with catalytic amount of pyrrolidine/HOAc at room temperature has been developed. This method offers a chemoselective, one-pot cascade access to δ-keto α-cyano esters with moderate to good yields under mild conditions.

  已经开发出在室温下α-氰基酯，醛和酮与催化量的吡咯烷/ HOAc的顺序缩合。该方法可在温和条件下以中等到良好的产率对δ-酮基α-氰基酯进行化学选择性的一锅级联反应。
• El-Sadany, S K; Sharaf, S M; Darwish, A I, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 6, p. 567 - 573
  作者：El-Sadany, S K、Sharaf, S M、Darwish, A I、Youssef, A A

  DOI：——

  日期：——
• Darwish, A. I., Egyptian Journal of Chemistry, 2002, vol. 45, # 4, p. 695 - 711
  作者：Darwish, A. I.

  DOI：——

  日期：——
• Immobilization of lipase on Fe3O4/ZnO core/shell magnetic nanoparticles and catalysis of Michael-type addition to chalcone derivatives
  作者：Sabrieh Ghasemi、Marjan Heidary、Mohammad Ali Faramarzi、Zohreh Habibi

  DOI：10.1016/j.molcatb.2013.12.006

  日期：2014.2

  Fe3O4/ZnO core/shell magnetic nanoparticles in 1:1 and 1:2 molar ratios were prepared and characterized by using X-ray powder diffraction, scanning electron microscopy, thermogravimetric analysis, FT-IR spectra, and flame atomic absorption spectrophotometry. Thermomyces lanuginosa lipase (TLL) was then covalently immobilized on the surface of both supports. An immobilization efficiency and yield of 94 +/- 2.5% and 86 +/- 3.5%, respectively, were measured for nanoparticles in 1:1 molar ratio of Fe3O4/ZnO and immobilization efficiency and yield were 89 +/- 2.2% and 81 +/- 3.1%, respectively, when lipase was bound to the functionalized nanoparticles in 1:2 molar ratio. The obtained result indicated that the immobilization considerably improved thermal, pH, and operational stability of TLL compared to the soluble enzyme. Moreover, the immobilized enzyme and seven other commercially lipases were examined for Micheal addition of active methylene compounds to chalcones. TLL resulted in the highest yield of the related reaction product compared to other enzymes. For further optimization of Micheal reaction conditions, the effect of some organic solvents was also examined and the obtained results revealed that hydrophobic solvents were more suitable than others. (C) 2013 Elsevier B.V. All rights reserved.