ethyl ester of trans-4-hydroxy-3,5-di-tert-butylcinnamic acid | 147167-96-2

• 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: ethyl ester of trans-4-hydroxy-3,5-di-tert-butylcinnamic acid
• 英文别名: ethyl 4-hydroxy-3,5-di-tert-butylcinnamate；Cinnamic acid, 3,5-di-tert-butyl-4-hydroxy-, ethyl ester；ethyl (E)-3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoate
• CAS: 147167-96-2
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: ALUDCPPKWVUVDT-MDZDMXLPSA-N

物化性质

• 沸点：
  378.4±37.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl ester of trans-4-hydroxy-3,5-di-tert-butylcinnamic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、800.01 kPa 条件下， 生成 3-(3,5-二-叔丁基-4-羟基苯基)丙酸乙酯
  参考文献：
  名称：

  High Yield Synthesis of Spirocyclic Dienones from Phenols Employing Tribromide Catalysed Dearomatization

  摘要：

  A catalytic strategy towards the tribromide‐catalyzed dearomative spirocyclization reaction is described employing tetrabutylammonium bromide (TBAB) and oxone as an oxidising agent. This methodology leads to the exclusive formation of spirofurano dienones without rearomatization or halogenation. Our group has been on trails of tribromide‐catalyzed dearomative transformation during the last decade, and now this exhibits the first report which delivers high functional group tolerance and broad substrate scope with excellent yield (up to 99%) and good diastereoselectivity (dr up to 14:1). The oxidation of naphthols as well as phenols is achieved under this mild conditions.

  DOI：

  10.1002/ejoc.202400267
• 作为产物：
  描述：

  2,6-二叔丁基苯酚 在 sodium hydroxide 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 生成 ethyl ester of trans-4-hydroxy-3,5-di-tert-butylcinnamic acid
  参考文献：
  名称：

  High Yield Synthesis of Spirocyclic Dienones from Phenols Employing Tribromide Catalysed Dearomatization

  摘要：

  A catalytic strategy towards the tribromide‐catalyzed dearomative spirocyclization reaction is described employing tetrabutylammonium bromide (TBAB) and oxone as an oxidising agent. This methodology leads to the exclusive formation of spirofurano dienones without rearomatization or halogenation. Our group has been on trails of tribromide‐catalyzed dearomative transformation during the last decade, and now this exhibits the first report which delivers high functional group tolerance and broad substrate scope with excellent yield (up to 99%) and good diastereoselectivity (dr up to 14:1). The oxidation of naphthols as well as phenols is achieved under this mild conditions.

  DOI：

  10.1002/ejoc.202400267

文献信息

• Electrochemical Oxidative Coupling of 4-Hydroxycinnamic Ester Derivatives: A Convenient Methodology for the Biomimetic Synthesis of Lignin Precursors
  作者：Anne Neudorffer、Brigitte Deguin、Céline Hamel、Maurice-Bernard Fleury、Martine Largeron

  DOI：10.1135/cccc20031515

  日期：——

  Based on the electrochemical oxidative coupling of 4-hydroxycinnamic ester derivatives, a straightforward biomimetic synthesis of lignin precursors is reported. This one-pot procedure leads to various naturally occurring coupling products whose distribution depends on aromatic substituents.

  基于4-羟基肉桂酸酯衍生物的电化学氧化偶联反应，报道了一种简单的仿生合成木质素前体的方法。这种一锅法过程可以产生多种天然的偶联产物，其分布取决于芳香基取代基。
• Dual Inhibition of Human Leukocyte Elastase and Lipid Peroxidation:  <i>In Vitro</i> and <i>in Vivo</i> Activities of Azabicyclo[2.2.2]octane and Perhydroindole Derivatives
  作者：Bernard Portevin、Michel Lonchampt、Emmanuel Canet、Guillaume De Nanteuil

  DOI：10.1021/jm960772z

  日期：1997.6.1

  A series of potent and selective human leukocyte elastase (HLE) inhibitors of the Val-Pro-Val type has been developed. Initially, the central proline residue was replaced by nonnatural amino acids Phi ((2S,3aS,7aS)-perhydroindole-2-carboxy acid) and Abo ((3S)-2-azabicyclo[2.2.2]octane-3-carboxylic acid), and secondly several groups able to confer antioxidant properties to the molecule were introduced at the lipophilic N-terminal side chain. When compared to reference inhibitors, in vitro HLE inhibitory potency was maintained (10-100 nM) both with compounds containing the antioxidant moiety at the end of the N-terminal side chain and with compounds in which the N-terminal valine of the tripeptidic sequence had been replaced by a epsilon-substituted lysine. The lipidic peroxidation inhibitory potency of this series of inhibitors was found to be similar to that of the reference antioxidant compounds (around 1 mu M). Moreover, HLE-induced hemorrhage in the hamster lung was effectively prevented (40-60% at 15 mu g/ kg) by most of the inhibitors tested when administered intratracheally 3 h before instillation of elastase. Among the most active analogs, compounds 11a,c,g were still active when administered 18 h before elastase. Interestingly, compound 14a was able to prevent HLE-mediated lung damage when administered 72 h prior to enzymatic challenge, indicating exceptional stability and retention in the lung. Finally, in a 14-day chronic model of emphysema in the hamster, 14a significantly conserved alveolar spaces, a marker of lung tissue destruction, send was more potent; than reference inhibitor ICI 200 880. This indicates that addition of peroxidation inhibitory properties to an HLE inhibitor can provide a powerful in vivo inhibitor of pulmonary tissue destruction.
• Reaction of 6, 8-di-tert-butylspiro[4,5]deca-1-oxa-5,8-diene-2,7-dione with acid agents
  作者：A. A. Volod'kin、R. D. Malysheva、V. V. Ershov

  DOI：10.1007/bf00954174

  日期：1982.7
• Protective Effects of 4-Hydroxycinnamic Ethyl Ester Derivatives and Related Dehydrodimers against Oxidation of LDL:  Radical Scavengers or Metal Chelators?
  作者：Anne Neudörffer、Jean-Pierre Desvergne、Dominique Bonnefont-Rousselot、Alain Legrand、Maurice-Bernard Fleury、Martine Largeron

  DOI：10.1021/jf052923p

  日期：2006.3.1

  4-Hydroxycinnamate derivatives are known to be potent protectors against oxidation of low-density lipoproteins (LDL), via a combination of free radical scavenging and transition metal chelation. Through a series of 4-hydroxycinnamic ethyl ester derivatives and related 8-8 dehydrodimers, we have tried to bring out the structural requirements for radical scavenging and cupric ion chelation. We found that the monomeric compounds, except for highly lipophilic tert-butyl derivative 3, exhibited rather low radical scavenging properties. Furthermore, they did not chelate copper but, in contrast, reduced cupric ion to cuprous ion, affording the related 8-8 dehydrodimers, for which they could be considered as precursors in vitro. In the copper-dependent human LDL oxidation in vitro, the cyclic 8-8 dehydrodimer forms behaved essentially as efficient copper chelators, while related noncyclic 8-8 forms, which were found to be the best protectors, mainly acted as radical scavengers.
• VOLODKIN, A. A.;MALYSHEVA, R. D.;ERSHOV, V. V., IZV. AN CCCP. CEP. XIM., 1982, N 7, 1633-1635
  作者：VOLODKIN, A. A.、MALYSHEVA, R. D.、ERSHOV, V. V.

  DOI：——

  日期：——