1-naphthyl cinnamate | 101936-99-6

• 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: 1-naphthyl cinnamate
• 英文别名: cinnamic acid-[1]naphthyl ester；Zimtsaeure-α-naphthylester；Zimtsaeure-[1]naphthylester；2-Propenoic acid, 3-phenyl-, 1-naphthalenyl ester；naphthalen-1-yl 3-phenylprop-2-enoate
• CAS: 101936-99-6
• 化学式: C₁₉H₁₄O₂
• 分子量: 274.319
• InChiKey: ILDQBAOOYYSRDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  109.5-110.5 °C
• 沸点：
  463.2±15.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  萘酚 、 肉桂酸 在 silica gel-supported Preyssler acid 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以95%的产率得到1-naphthyl 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

• Boron trichloride catalyzed ortho carbonylation of phenols:
  作者：Oreste Piccolo、Lucio Filippini、Laura Tinucci、Ermanno Valoti、Attilio Citterio

  DOI：10.1016/s0040-4020(01)87495-0

  日期：1986.1

  In the presence of equimolar quantity of BCl3, phenols 1 react with isocyanates and acyl chlorides to give, usually with good-excellent yields, 2-hydroxy-aryl-carboxy-amides 2 and 2-hydroxy-aryl-ketones 3 respectively. A distinctive behaviour of BCl3 in comparison with other Lewis acids is observed.

  在等摩尔量的BCl 3的存在下，酚1与异氰酸酯和酰氯反应，通常以优异的产率分别得到2-羟基-芳基-羧基酰胺2和2-羟基-芳基酮3。与其他路易斯酸相比，观察到BCl 3的独特行为。
• Edeleanu; Zaharia, vol. 3, p. 86
  作者：Edeleanu、Zaharia

  DOI：——

  日期：——