4-羟基-3-甲氧基苯甲酰胺 | 19072-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-羟基-3-甲氧基苯甲酰胺
• 英文名称: 4-hydroxy-3-methoxybenzamide
• 英文别名: vanillamide
• CAS: 19072-58-3
• 化学式: C₈H₉NO₃
• mdl: MFCD16998710
• 分子量: 167.164
• InChiKey: TZZAKSLHHIJRLL-UHFFFAOYSA-N

物化性质

• 熔点：
  153-154 °C
• 沸点：
  312.7±32.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-羟基-3-甲氧基苯甲酰胺 、 1,3-二溴丙烷 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 4-(3-bromopropoxy)-3-methoxybenzamide
  参考文献：
  名称：

  3-[[(Aryloxy)alkyl]piperidinyl]-1,2-Benzisoxazoles as D2/5-HT2 Antagonists with Potential Atypical Antipsychotic Activity: Antipsychotic Profile of Iloperidone (HP 873)

  摘要：

  A series of 3-[[(aryloxy)alkyl]piperidinyl]-1,2-benzisoxazoles was synthesized and evaluated as potential antipsychotic D-2/5-HT2 antagonists. Most of these compounds showed potent antipsychotic-like activity in an apomorphine-induced climbing mouse paradigm, with many also showing preferential mesolimbic activity, as indicated by their weaker effects in an apomorphine-induced stereotypy model. In receptor binding assays, many displayed a moderate affinity for the D-2 receptor coupled with a significantly greater affinity for the 5-HT2 receptor. a property that has been suggested as necessary for atypicality. From this series, compound 45, 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone (iloperidone, HP 873), was further evaluated in a battery of in vivo and in vitro assays. This compound showed a 300-fold greater potency in inhibition of climbing than in inhibition of stereotypy or induction of catalepsy, and when evaluated chronically in an electrophysiological model, 45 caused a depolarization blockade of dopamine neurons in the A10 area of the rat brain but not in the A9 area. Additionally, it showed positive activity in a social interaction paradigm, suggesting potential efficacy;against asociality, a component of the negative symptoms of schizophrenia. In chronic ex vivo studies, 45, similar to clozapine, caused a down regulation of 5-HT2 receptors but had no effect on the number of D-2 receptors. Compound 45 is currently undergoing clinical evaluation.

  DOI：

  10.1021/jm00007a009
• 作为产物：
  描述：

  香草醛 在 copper(ll) sulfate pentahydrate 、 盐酸羟胺 、 sodium acetate 作用下， 反应 6.0h， 以70%的产率得到4-羟基-3-甲氧基苯甲酰胺
  参考文献：
  名称：

  在纯净条件下，一种有效的铜（II）催化醛直接从伯酰胺中获取伯酰胺的方法

  摘要：

  使用盐酸羟胺（1摩尔当量），乙酸钠（1.1摩尔当量）和五水硫酸铜（5摩尔％），可以快速简便地一锅式将各种醛转化为相应的伯酰胺，并且收率良好至优异。 ）在110°C的纯净条件下。基于无配体铜（II）催化的方案避免了使用相对昂贵的后期过渡金属基催化剂，并且在操作简单的条件下进行，而无需任何要求分离和纯化产物的程序。

  DOI：

  10.1016/j.tetlet.2012.01.029

文献信息

• Highly efficient synthesis of primary amides <i>via</i> aldoximes rearrangement in water under air atmosphere catalyzed by an ionic ruthenium pincer complex
  作者：Fa-Liu Yang、Xinju Zhu、Dun-Kang Rao、Xiao-Niu Cao、Ke Li、Yan Xu、Xin-Qi Hao、Mao-Ping Song

  DOI：10.1039/c6ra07515k

  日期：——

  aldoximes to primary amides has been evaluated using pincer ruthenium complexes a–c, among which the ionic Ru catalyst a proved to be the most efficient in water under air atmosphere. A variety of (hetero)arene aldoximes proceeded smoothly to afford amides in high yields with good functional group compatibilities. Furthermore, a direct synthetic route of amides from aldehydes, hydroxylamine hydrochloride

  使用夹钳式钌络合物a–c评估了醛肟肟向伯酰胺的转化，其中离子Ru催化剂a被证明在空气中在水中是最有效的。各种（杂）芳烃醛肟可顺利进行，以高收率提供具有良好官能团相容性的酰胺。此外，还描述了由醛，盐酸羟胺和碳酸钠直接合成酰胺的途径，其底物包括共轭醛和脂族醛。该方案操作简单，并以低催化剂负载量（0.5摩尔％）进行。
• Iron-catalyzed arene C−H hydroxylation
  作者：Lu Cheng、Huihui Wang、Hengrui Cai、Jie Zhang、Xu Gong、Wei Han

  DOI：10.1126/science.abj0731

  日期：2021.10

  selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired l-cystine–derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation

  由于芳基碳氢键的相对惰性、酚类产物的较高反应性导致过度氧化的副产物以及经常不足的区域选择性，芳烃的可持续、非定向和选择性催化羟基化仍然是一项持续的研究挑战。我们报告说，铁由受生物启发的l-胱氨酸衍生的配体可以催化非定向芳烃碳氢羟基化，过氧化氢作为末端氧化剂。该反应以其广泛的底物范围、出色的选择性和良好的产率而著称，并且表现出与氧化敏感官能团的相容性，如醇、多酚、醛，甚至硼酸。该方法非常适合通过多重碳氢羟基化合成多酚，以及天然产物和药物分子的后期功能化。
• Enzymatic nitrile hydrolysis catalyzed by nitrilase ZmNIT2 from maize. An unprecedented β-hydroxy functionality enhanced amide formation
  作者：Chandrani Mukherjee、Dunming Zhu、Edward R. Biehl、Rajiv R. Parmar、Ling Hua

  DOI：10.1016/j.tet.2006.04.069

  日期：2006.6

  To explore the synthetic potential of nitrilase ZmNIT2 from maize, the substrate specificity of this nitrilase was studied with a diverse collection of nitriles. The nitrilase ZmNIT2 showed high activity for all the tested nitriles except benzonitrile, producing both acids and amides. For the hydrolysis of aliphatic, aromatic nitriles, phenylacetonitrile derivatives and dinitriles, carboxylic acids

  为了探索玉米中腈水解酶ZmNIT2的合成潜力，研究了该腈水解酶的底物特异性，并收集了多种腈。腈水解酶ZmNIT2对除苄腈以外的所有测试腈均显示高活性，同时生成酸和酰胺。对于脂族，芳族腈，苯乙腈衍生物和二腈的水解，羧酸是主要产物。出乎意料的是，发现酰胺是腈水解酶ZmNIT2催化的β-羟基腈水解的主要产物。酶-底物复杂中间体中羟基和氮之间的氢键不利于氨的损失和酰基-酶中间体的形成，后者进一步水解为酸，
• Cysteine derivatives
  申请人：AJINOMOTO CO., INC.

  公开号：US20020115723A1

  公开（公告）日：2002-08-22

  Objects of the present invention are to provide an oxidative stress inhibitor which is capable of suppressing the expression of a cytotoxic protein and the activation of a gene transcriptional regulatory factor taking part such expression of a cytotoxic protein and exhibits good feeling upon use and safety; to provide a method for preventing, retarding, alleviating or treating a skin change due to aging or an undesirable aesthetic skin change, both caused or promoted by an oxidative stress; and to provide a cosmetic composition or dermatologic preparation for external use comprising the oxidative stress inhibitor as an effective ingredient, and for those purposes are employed an oxidative stress inhibiting agent which comprises, as an effective ingredient, at least one selected from cysteine or cystine derivatives and the salts thereof.

  本发明的目的是提供一种能够抑制细胞毒蛋白表达和基因转录调节因子激活的氧化应激抑制剂，该抑制剂在使用时具有良好的感觉和安全性；提供一种预防、延缓、缓解或治疗由氧化应激引起或促进的皮肤老化或不良美容皮肤变化的方法；提供一种含有氧化应激抑制剂作为有效成分的用于外用的化妆品组合物或皮肤科制剂。为了实现这些目的，使用一种氧化应激抑制剂，其有效成分包括至少一种来自半胱氨酸或半胱氨酸衍生物及其盐的物质。
• [DE] VERWENDUNG VON ALKYLOXYALKANSÄUREAMIDEN INSBESONDERE ALS AROMASTOFFE SOWIE NEUE ALKYLOXYALKANSÄUREAMIDE<br/>[EN] USE OF ALKYLOXYALCANIC ACID AMIDES, IN PARTICULAR IN THE FORM OF AROMATIC SUBSTANCES AND A NOVEL ALKYLOXYALCANIC ACID AMIDE<br/>[FR] UTILISATION D'AMIDES DE L'ACIDE ALKYLOXYALCANIQUE, NOTAMMENT COMME AROMATISANTS, ET NOUVEL AMIDE DE L'ACIDE ALKYLOXYALCANIQUE
  申请人：SYMRISE GMBH & CO KG

  公开号：WO2006003210A1

  公开（公告）日：2006-01-12

  Beschrieben wird die Verwendung bestimmter Alkyloxyalkansäureamide als (i) Aromastoff und/oder (ii) zur Erzeugung eines Gefühls von Kribbeln und/oder (iii) zur Erzeugung eines Gefühls von Schärfe und/oder (iv) zur Anregung des Speichelfusses im Mund und/oder (v) zur Verstärkung des Geschmacks von Ethanol und/oder (vi) zur Imitierung des Geschmacks von Ethanol.

  描述了特定的烷氧基烷基酰胺的用途，作为（i）香料和/或（ii）产生刺痛感和/或（iii）产生辛辣感和/或（iv）刺激口腔中的唾液分泌和/或（v）增强乙醇的味道和/或（vi）模拟乙醇的味道。