(E)-octyl 3-(4-hydroxyphenyl)acrylate | 1206615-65-7

• 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: (E)-octyl 3-(4-hydroxyphenyl)acrylate
• 英文别名: trans-octyl 3-(4-hydroxyphenyl)propenoate；octyl trans-3-(4-hydroxyphenyl) propanoate；octyl p-coumarate；Octyl 3-(4-hydroxyphenyl)prop-2-enoate；octyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• CAS: 1206615-65-7
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: JSLXRMDKYVPFAJ-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-香豆酸 在 碘 、 zinc trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 4.17h， 生成 (E)-octyl 3-(4-hydroxyphenyl)acrylate
  参考文献：
  名称：

  Zn(OTf)₂-Promoted Chemoselective Esterification of Hydroxyl Group Bearing Carboxylic Acids

  摘要：

  Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I-2, and a catalytic amount of Zn(OTf)(2). Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from trans-esterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.

  DOI：

  10.1021/jo302502r

文献信息

• Effects of Surfactant Volume Fraction on the Antioxidant Efficiency and on The Interfacial Concentrations of Octyl and Tetradecyl p-Coumarates in Corn Oil-in-Water Emulsions
  作者：Marlene Costa、Sonia Losada-Barreiro、Fátima Paiva-Martins、Carlos Bravo-Díaz

  DOI：10.3390/molecules26196058

  日期：——

  coalescence by forming steric barriers. However, addition of surfactants to binary oil-water mixtures also brings up the formation of three-dimensional interfacial layers, surrounding each emulsion droplet, that significantly alter chemical reactivity. This is the case, for instance, in the inhibition reaction between antioxidants and the lipid radicals formed in the course of the spontaneous oxidation

  几十年来，表面活性剂已在食品工业中用于制备基于脂质的乳化食品。它们在乳化过程中起两个主要作用：首先，它们降低油水之间的界面张力，促进液滴变形和破裂；其次，它们通过形成空间势垒来减少液滴聚结。然而，在二元油水混合物中添加表面活性剂也会形成三维界面层，围绕每个乳液液滴，这显着改变了化学反应性。例如，抗氧化剂与不饱和脂质自发氧化反应过程中形成的脂质自由基之间的抑制反应就是这种情况，通常用于制备食品级乳液。抑制反应的速率取决于抗氧化剂的有效浓度，而抗氧化剂的有效浓度主要受制备乳液时所用表面活性剂的量控制。在这项工作中，我们分析了表面活性剂吐温 20 对氧化稳定性和肉桂酸衍生的两种模型抗氧化剂有效浓度的影响，确定它们在完整乳液中的界面浓度，以避免破坏现有的平衡和偏差结果。为此，采用了最近开发的方法，并在假相动力学模型的基础上解释了实验结果。我们分析了表面活性剂吐温 20 对氧化稳定性和肉桂酸衍生的两
• 一种对香豆酸酯及其合成方法与应用
  申请人：华南理工大学

  公开号：CN113402392B

  公开（公告）日：2023-04-28
• Discovery of neurotrophic agents based on hydroxycinnamic acid scaffold
  作者：Razieh Hosseini、Fatemeh Moosavi、Hamid Rajaian、Tiago Silva、Diogo Magalhães e Silva、Pedro Soares、Luciano Saso、Najmeh Edraki、Ramin Miri、Fernanda Borges、Omidreza Firuzi

  DOI：10.1111/cbdd.12829

  日期：2016.12

  The number of people affected by neurodegenerative disorders such as Alzheimer's disease and Parkinson's disease is rapidly increasing owing to the global increase in life expectancy. Small molecules with neurotrophic effects have great potential for management of these neurological disorders. In this study, different (C1–C12) alkyl ester derivatives of hydroxycinnamic acids (HCAs) were synthesized (a total of 30 compounds). The neurotrophic capacity of the test compounds was examined by measuring promotion of survival in serum‐deprived conditions and enhancement of nerve growth factor (NGF)‐induced neurite outgrowth in PC12 neuronal cells. p‐Coumaric, ferulic, and sinapic acids and their esters did not alter cell survival, while caffeic acid and all its alkyl esters, especially decyl and dodecyl caffeate, significantly promoted neuronal survival at 25 μm. Methyl, ethyl, propyl, and butyl caffeate esters also significantly enhanced NGF‐induced neurite outgrowth, among which the most effective ones were propyl and butyl esters, which at 5 μm led to 25‐ and 22‐fold increases in the number of neurites, respectively. The findings of the docking study suggested phosphatidylinositol 3‐kinase (PI3K) as the potential molecular target. In conclusion, our findings demonstrate that alkyl esters of caffeic acid can be useful as scaffolds for the discovery of therapeutic agents for neurodegenerative diseases.
• Zn(OTf)₂-Promoted Chemoselective Esterification of Hydroxyl Group Bearing Carboxylic Acids
  作者：Narsimha Mamidi、Debasis Manna

  DOI：10.1021/jo302502r

  日期：2013.3.15

  Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I-2, and a catalytic amount of Zn(OTf)(2). Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from trans-esterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.