2-(N-phthalimido)ethyl cinnamate | 463353-77-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-(N-phthalimido)ethyl cinnamate
• 英文别名: 2-phthalimidoethyl cinnamate；2-(1,3-Dioxoisoindol-2-yl)ethyl 3-phenylprop-2-enoate
• CAS: 463353-77-7
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: XEDBYYXKMTYTDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-羟乙基酞酰亚胺 、 肉桂酸 在 silica gel-supported Preyssler acid 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以83%的产率得到2-(N-phthalimido)ethyl cinnamate
  参考文献：
  名称：

  Preyssler catalyst: An efficient catalyst for esterification of cinnamic acids with phenols and imidoalcohols

  摘要：

  In the present work a series of eco-friendly Preyssler solid acids and their salts H(14)[NaP(5)W(29)MoO(110)] (M), H(14)[NaP(5)W(30)O(110)] (PWMo). K(12.5)Na(1.5)[NaP(5)W(30)O(110)]center dot 15H(2)O (PWK), K(12.5)Na(1.5)[NaP(5)W(29-)MoO(110)]center dot 15H(2)O (PWMoK) and 10% silica-supported H(14)[NaP(5)W(29)MoO(110)] (PWSiO(2)), and H(14)[NaP(5)W(30)O(110)] (PWMoSiO(2)) have been used as catalysts for the direct esterification of cinnamic acids with phenols or 2-(N-phthalimidoethanol). Effects of the reaction conditions were studied, including temperature, reaction time, and type and amount of catalyst. These solids were characterized by several techniques, such as diffuse reflectance spectroscopy, Fourier transformed infrared spectroscopy, optical and scanning electron microcopies, and X-ray diffraction, among others.The most adequate catalyst for performing the title reaction was H(14)[NaP(5)W(30)O(110)] (PWMo). The catalyst was applied for the synthesis of various substituted cinnamates, giving very good yields. (c) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2009.11.037

文献信息

• Preyssler catalyst: An efficient catalyst for esterification of cinnamic acids with phenols and imidoalcohols
  作者：Diego M. Ruiz、Gustavo P. Romanelli、Patricia G. Vázquez、Juan C. Autino

  DOI：10.1016/j.apcata.2009.11.037

  日期：2010.2

  In the present work a series of eco-friendly Preyssler solid acids and their salts H(14)[NaP(5)W(29)MoO(110)] (M), H(14)[NaP(5)W(30)O(110)] (PWMo). K(12.5)Na(1.5)[NaP(5)W(30)O(110)]center dot 15H(2)O (PWK), K(12.5)Na(1.5)[NaP(5)W(29-)MoO(110)]center dot 15H(2)O (PWMoK) and 10% silica-supported H(14)[NaP(5)W(29)MoO(110)] (PWSiO(2)), and H(14)[NaP(5)W(30)O(110)] (PWMoSiO(2)) have been used as catalysts for the direct esterification of cinnamic acids with phenols or 2-(N-phthalimidoethanol). Effects of the reaction conditions were studied, including temperature, reaction time, and type and amount of catalyst. These solids were characterized by several techniques, such as diffuse reflectance spectroscopy, Fourier transformed infrared spectroscopy, optical and scanning electron microcopies, and X-ray diffraction, among others.The most adequate catalyst for performing the title reaction was H(14)[NaP(5)W(30)O(110)] (PWMo). The catalyst was applied for the synthesis of various substituted cinnamates, giving very good yields. (c) 2009 Elsevier B.V. All rights reserved.