香草基扁桃酸乙酯 | 52058-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 香草基扁桃酸乙酯
• 中文别名: 香草醛酸乙酯
• 英文名称: ethyl 4-hydroxy-3-methoxymandelate
• 英文别名: Vanillylmandelic Acid Ethyl Ester；ethyl 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetate
• CAS: 52058-11-4
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: JANQOURSKMXOPR-UHFFFAOYSA-N

物化性质

• 熔点：
  70 - 73°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  香草基扁桃酸乙酯 在 sodium hydroxide 作用下， 生成 3-甲氧基-4-羟基扁桃酸
  参考文献：
  名称：

  Studies on Lignin and Related Compounds. LXXXII. Synthesis and Properties of 1,3-Diacetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-propanone and 1-Acetoxy-3-chloro-1-(4-acetoxy-3-methoxyphenyl)-2-propanone and their Relation to Lignin Structure¹

  摘要：

  DOI：

  10.1021/ja01232a029
• 作为产物：
  描述：

  溴乙烷 、 3-甲氧基-4-羟基扁桃酸 在 caesium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以77%的产率得到香草基扁桃酸乙酯
  参考文献：
  名称：

  铃木-Miyaura偶联反应制备2,3,3-三芳基丙烯酸酯

  摘要：

  摘要 我们在这里报告了一种生产2,3,3-三芳基丙烯酸酯的新策略，该酯是一类具有α，β-不饱和酯官能度的1,2,2-三芳基乙烯化合物。我们的方法要求由α-酮基酯制备宝石-二溴烯烃前体，然后通过Suzuki-Miyaura偶联反应在两个C-Br键上安装两个芳基。在大多数情况下，获得了具有1、2或3个不同芳基的许多2,3,3-三芳基丙烯酸酯。 我们在这里报告了一种生产2,3,3-三芳基丙烯酸酯的新策略，该酯是一类具有α，β-不饱和酯官能度的1,2,2-三芳基乙烯化合物。我们的方法要求由α-酮基酯制备宝石-二溴烯烃前体，然后通过Suzuki-Miyaura偶联反应在两个C-Br键上安装两个芳基。在大多数情况下，获得了具有1、2或3个不同芳基的许多2,3,3-三芳基丙烯酸酯。

  DOI：

  10.1055/s-0035-1560419

文献信息

• Synthesis and anti-inflammatory activity of isoquebecol
  作者：Sébastien Cardinal、Pierre-Alexandre Paquet-Côté、Jabrane Azelmat、Corinne Bouchard、Daniel Grenier、Normand Voyer

  DOI：10.1016/j.bmc.2017.01.050

  日期：2017.4

  We report here the synthesis of isoquebecol, an unprecedented constitutional isomer of quebecol, a polyphenolic compound discovered in maple syrup. The methodology used to prepare isoquebecol involves, as key steps, the formation of a dibromoalkene from an α-ketoester precursor, followed by a double Suzuki-Miyaura reaction. The anti-inflammatory activity of isoquebecol was studied on macrophage cells

  我们在这里报告了异方苯酚的合成，异方苯酚是枫糖浆中发现的多酚化合物quebecol的前所未有的结构异构体。制备异白酚的方法学涉及关键步骤，即由α-酮酸酯前体形成二溴代烯烃，然后进行Suzuki-Miyaura双反应。通过监测其抑制LPS诱导的IL-6分泌的能力，研究了异黄柏对巨噬细胞的抗炎活性。结果表明，这种新化合物具有比其天然异构体更高的生物活性。这项研究中还制备了quebecol，异quebecol和模型类似物2,3,3-三苯丙醇的前体和衍生物。
• Reaction of vanilmandelic acid and 4-hydroxybenzyl alcohol derivatives with L-ascorbic acid
  作者：M.N. Preobrazhenskaya、I.I. Rozhkov、E.I. Lazhko、L.N. Yudina、A.M. Korolev

  DOI：10.1016/s0040-4020(97)00396-7

  日期：1997.5

  The interaction between vanilmandelic and L-ascorbic acids led to a cyclopent-2-en-one derivative, whereas the reaction of methyl vanilmandelate with L-ascorbic acid yielded 2-furancarboxylic acid as the major product. The model 3-substituted 4-hydroxybenzyl alcohols and L-ascorbic acid produced ascorbigen-type structures, which easily decarboxylated to give mixtures of the corresponding l-aryl-l-deoxyketoses

  香草醛扁桃酸酯和L-抗坏血酸之间的相互作用产生了环戊-2-烯一衍生物，而香草醛扁桃酸甲酯与L-抗坏血酸的反应产生了2-呋喃羧酸作为主要产物。模型3-取代的4-羟基苄醇和L-抗坏血酸产生抗坏血酸型结构，其易于脱羧而得到相应的1-芳基-1-脱氧酮糖的混合物。
• Discovery of rapid spectral variability in the Ap star χ Psc
  作者：S. G. Aliev、N. Z. Ismailov

  DOI：10.1134/1.1320499

  日期：2000.11

  Analysis of spectrograms with high spectral and temporal resolution taken during four nights in 1998 has revealed spectral-line variability of the peculiar star HD 220825 with a quasi-period of $$0\mathop d\limits_. 0.12 \pm 0\mathop d\limits_. 0005$$ . The observed variations have the form of wavelike oscillations whose amplitude decreases or increases during the observations. The CrII, SiII, and TiII lines exhibit the strongest variability. The scale lengths of peculiar regions are estimated to be from 5000 to 15000 km based on data for different lines. The results provide evidence for the presence of real wavelike dynamical processes at the stellar surface that change the physical conditions in the stellar atmosphere.

  对1998年四个晚上拍摄的高光谱和时间分辨率的光谱图进行分析，发现了奇特恒星HD 220825的光谱线变率，其准周期为$0\mathop d\limits_.0.12 \pm 0\mathop d\limits_.0005$$ .观测到的变化是波状振荡，振幅在观测过程中时大时小。CrII、SiII 和 TiII 线的变化最强。根据不同谱线的数据，奇特区域的尺度长度估计在 5000 至 15000 公里之间。这些结果为恒星表面存在真正的波状动力学过程，从而改变恒星大气中的物理条件提供了证据。
• Anti-inflammatory properties of quebecol and its derivatives
  作者：Sébastien Cardinal、Jabrane Azelmat、Daniel Grenier、Normand Voyer

  DOI：10.1016/j.bmcl.2015.11.096

  日期：2016.1

  Herein we report our results on the anti-inflammatory activity of quebecol, a polyphenolic compound discovered in maple syrup. Bioassays demonstrated that quebecol has an anti-inflammatory effect on LPS-induced NF-kappa B activation and inhibits the secretion of two pro-inflammatory cytokines, IL-6 and TNF-alpha. We also prepared and tested precursors of quebecol and its derivatives corresponding to its substructures of interest, with the aim to study the structure-activity relationships. Comparing the results obtained for all tested compounds allowed the identification of the main moiety responsible for the anti-inflammatory activity of quebecol. (C) 2015 Elsevier Ltd. All rights reserved.
• Total synthesis of quebecol
  作者：Sébastien Cardinal、Normand Voyer

  DOI：10.1016/j.tetlet.2013.07.048

  日期：2013.9

  We report here the total synthesis of quebecol, a new polyphenolic compound with potential applications recently isolated from maple syrup and produced during the condensation of the tree acer saccharum's sap. The synthetic approach we developed involves, as key steps, the formation of a dibromoalkene from an alpha-ketoester precursor followed by a double Suzuki-Miyaura reaction to unite the three aromatic rings of the target compound on a tetrasubstituted olefin precursor. Our methodology is an efficient pathway to the target compound and leads the way for future analogs. (C) 2013 Elsevier Ltd. All rights reserved.