N-(3,4-dimethoxybenzyl)nonanamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3,4-dimethoxybenzyl)nonanamide
• 英文别名: N-[(3,4-dimethoxyphenyl)methyl]nonanamide
• 化学式: C₁₈H₂₉NO₃
• 分子量: 307.433
• InChiKey: KULLVDQTQMNXKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethoxybenzyl)nonanamide 在 三溴化硼 、 柠檬酸 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 以80%的产率得到N-(3,4-dihydroxybenzyl)nonanamide
  参考文献：
  名称：

  一种苄胺酰类衍生物及其在制备抗炎药物中的用途

  摘要：

  本发明提供了式A所示的化合物、或其药学上可接受的盐、或其溶剂合物，及其在在制备抗炎药物中的用途。实验证明本发明制备的式A所示的化合物能够显著抑制LPS诱导的NO产生，具有较强的抗炎能力，并且细胞毒性小，可以应用于临床上抗炎药物的制备。

  公开号：

  CN109879772B
• 作为产物：
  描述：

  4-(氨基甲基)-2-甲氧基苯酚盐酸盐 在 potassium carbonate 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 N-(3,4-dimethoxybenzyl)nonanamide
  参考文献：
  名称：

  Analogs of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 1. The aromatic "A-region"

  摘要：

  A series of analogues of capsaicin, the pungent principle of chilli peppers, was synthesized and tested in assays for capsaicin-like agonism in vitro. The results of these assays were compared with activities in an acute nociceptive model and a correlation was observed which established that the results of these in vitro assays were predictive of analgesia. Using a modular approach the structure-activity profile of specific regions of capsaicin congeners was established using an in vitro assay measuring Ca-45(2+) uptake into neonatal rat dorsal root ganglia neurones. Substituted benzylnonanamides 2a-z and N-octyl-substituted phenylacetamides 4a-v were made to test the requirements for activity in the aromatic ''A-region'' of the molecule. Compounds with the natural substitution pattern (2b and 4c) and the corresponding catechols (2i and 4g) were the most potent, although the catechols were less potent in vivo. Other substitution patterns have reduced activity. These results have established stringent structural requirements for capsaicin-like activity in this part of the molecule.

  DOI：

  10.1021/jm00068a014

文献信息

• Studies on the synthesis, pungency and anti-biofouling performance of capsaicin analogues
  作者：BiXian Peng、JunLian Wang、ZhengHong Peng、ShengZe Zhou、FengQi Wang、YongLiang Ji、ZhangJi Ye、XiangFeng Zhou、Tong Lin、XiaoBin Zhang

  DOI：10.1007/s11426-011-4307-x

  日期：2012.3

  Ten capsaicin analogues were synthesized and their pungency degrees were determined through Scoville Organoleptic Test. The relationship between the structure and pungency degree of these capsaicin analogues was discussed. Then four of these capsaicin analogues with higher pungency degree were picked out and added to anti-biofouling paints as repellents to study their anti-biofouling performance by shallow sea buoyant raft hung-plate experimentation. The results showed that capsaicin and dihydrocapsaicin exhibited equally good anti-biofouling performance while nordihydrocapsaicin and N-vanillylnonanamide had poor anti-biofouling performance. Experimental results also showed that the paints with only 0.1% capsaicin or dihydrocapsaicin as repellent without any other biocides had also exhibited good anti-biofouling performance, which provided a new idea for developing novel, more environment-friendly and Cu2O-free antifouling paints.

  合成了十种辣椒素类似物并测定了其辛烈程度，通过史高维尔感官测试法确定了这些辣椒素类似物的结构与辛烈程度之间的关系。从中选出四种辛烈程度较高的辣椒素类似物加入防污涂料中作为驱避剂，通过浅海漂浮木排挂板实验来研究其防污性能。研究结果表明：高辛烈性的辣椒碱和二氢辣椒碱表现出良好的防污性能，而高辛烈性的降二氢辣椒碱和非对称二氢辣椒酰胺表现出较差的防污性能。实验结果还表明，单纯添加了 0.1%高辛烈性辣椒酰胺或二氢辣椒酰胺的涂料表现出良好的防污性能，这为今后无铜环保型防污涂料的开发提供了一条新思路。
• [EN] PRODRUGS OF PHENOLIC TRPV1 AGONISTS<br/>[FR] PROMÉDICAMENTS D'AGONISTES DU TRPV1 PHÉNOLIQUE
  申请人：CONCENTRIC ANALGESICS INC

  公开号：WO2017147146A1

  公开（公告）日：2017-08-31

  Described herein are compounds, pharmaceutical compositions and medicaments that include such compounds, and methods of using such compounds to modulate transient receptor potential vanilloid 1 receptor (TRPV1) activity.

  本文描述了包括这些化合物的化合物、药物组合物和药物，以及使用这些化合物调节瞬时受体电位香草醛1受体（TRPV1）活性的方法。
• Integrated Heterogeneous Metal/Enzymatic Multiple Relay Catalysis for Eco-Friendly and Asymmetric Synthesis
  作者：Carlos Palo-Nieto、Samson Afewerki、Mattias Anderson、Cheuk-Wai Tai、Per Berglund、Armando Córdova

  DOI：10.1021/acscatal.6b01031

  日期：2016.6.3

  sequences (reductive amination/amidation, aerobic oxidation/reductive amination/amidation, reductive amination/kinetic resolution and reductive amination/dynamic kinetic resolution) were developed. They were next applied to the direct synthesis of various biologically and optically active amines or amides in one-pot from simple aldehydes, ketones, or alcohols, respectively.

  通常使用逐步转化来进行有机合成，其中通常需要在进一步反应之前分离和纯化关键中间体。本文中，我们公开了使用非均相金属和酶催化剂的组合，在一个锅中以生态友好和不对称方式合成有价值分子（例如胺和酰胺）的非均相金属/酶多重中继集成催化的概念。在此，可以在涉及多步催化串联操作的一锅法中引入试剂，催化剂和不同条件。开发了几种新颖的共催化中继序列（还原胺化/酰胺化，有氧氧化/还原胺化/酰胺化，还原胺化/动力学拆分和还原胺化/动态动力学拆分）。
• [EN] PEGYLATED PRODRUGS OF PHENOLIC TRPV1 AGONISTS<br/>[FR] PROMÉDICAMENTS PEGYLÉS D'AGONISTES DU TRPV1 PHÉNOLIQUE
  申请人：CONCENTRIC ANALGESICS INC

  公开号：WO2020023793A1

  公开（公告）日：2020-01-30

  Described herein are compounds, pharmaceutical compositions and medicaments that include such compounds, and methods of using such compounds to modulate transient receptor potential vanilloid 1 receptor (TRPV1) activity.

  本文描述了包括这些化合物的化合物、药物组合物和药物，以及使用这些化合物调节瞬时受体电位香草醛1受体（TRPV1）活性的方法。
• PEGYLATED PRODRUGS OF PHENOLIC TRPV1 AGONISTS
  申请人：CONCENTRIC ANALGESICS, INC.

  公开号：US20200031780A1

  公开（公告）日：2020-01-30

  Described herein are compounds, pharmaceutical compositions and medicaments that include such compounds, and methods of using such compounds to modulate transient receptor potential vanilloid 1 receptor (TRPV1) activity.

  本文描述了包括这些化合物的化合物、药物组合物和药物，以及使用这些化合物调节瞬时受体电位香草醛1受体（TRPV1）活性的方法。