4-((diethylamino)methyl)phenol | 24619-86-1

• 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: 4-((diethylamino)methyl)phenol
• 英文别名: 4-[(Diethylamino)methyl]phenol；4-(diethylaminomethyl)phenol
• CAS: 24619-86-1
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: MAFHOFLRHFJFSE-UHFFFAOYSA-N

物化性质

• 熔点：
  79 °C
• 沸点：
  265.7±15.0 °C(Predicted)
• 密度：
  1.010±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((diethylamino)methyl)phenol 在 四丁基溴化铵 、 sodium hydride 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2,3-diamino-N2-(2-(4-((diethylamino)methyl)phenoxy)ethyl)quinoxaline
  参考文献：
  名称：

  Searching for the Multi-Target-Directed Ligands against Alzheimer’s disease: Discovery of quinoxaline-based hybrid compounds with AChE, H3R and BACE 1 inhibitory activities

  摘要：

  A novel series of quinoxaline derivatives, as Multi-Target-Directed Ligands (MTDLs) for AD treatment, were designed by lending the core structural elements required for H3R antagonists and hybridizing BACE 1 inhibitor 1 with AChE inhibitor BYYT-25. A virtual database consisting of quinoxaline derivatives was first screened on a pharmacophore model of BACE 1 inhibitors, and then filtered by a molecular docking model of AChE. Seventeen quinoxaline derivatives with high score values were picked out, synthesized and evaluated for their biological activities. Compound 11a, the most effective MTDL, showed the potent activity to H3R/AChE/BACE 1 (H3R antagonism, IC50 = 280.0 +/- 98.0 nM; H3R inverse agonism, IC50 = 189.3 +/- 95.7 nM; AChE, IC50 = 483 +/- 5 nM; BACE 1, 46.64 +/- 2.55% inhibitory rate at 20 mu M) and high selectivity over H1R/H2R/H4R. Furthermore, the protein binding patterns between 11a and AChE/BACE 1 showed that it makes several essential interactions with the enzymes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.061
• 作为产物：
  描述：

  N-乙基-N-[(4-甲氧基苯基)甲基]乙胺 在 氢溴酸 作用下， 生成 4-((diethylamino)methyl)phenol
  参考文献：
  名称：

  US2783277

  摘要：

  公开号：

文献信息

• Reactivity of new precursors of quinone methides
  作者：Bernard Loubinoux、Joseph Miazimbakana、Philippe Gerardin

  DOI：10.1016/s0040-4039(00)99619-9

  日期：1989.1

  The azidomethylene protecting group allows the synthesis of unstable phenolic compounds which are used as quinone methide precursors in the alkylations of alcohols, phenols, azide, thiophenol, amines, enols and enolates.

  叠氮基亚甲基保护基团允许合成不稳定的酚类化合物，在醇，酚，叠氮化物，硫酚，胺，烯醇和烯醇化物的烷基化中用作醌甲基化物前体。
• Simplified preparation of a graphene-co-shelled Ni/NiO@C nano-catalyst and its application in the <i>N</i>-dimethylation synthesis of amines under mild conditions
  作者：Jianguo Liu、Yanpei Song、Xiuzheng Zhuang、Mingyue Zhang、Longlong Ma

  DOI：10.1039/d1gc00981h

  日期：——

  selective synthesis of N-methylated compounds using various functional amines and aldehydes under easy to handle, and industrially applicable conditions. A large number of primary and secondary amines (more than 70 examples) could be converted to the corresponding N,N-dimethylamines with the participation of different functional aldehydes, with an average yield of over 95%. A gram-scale synthesis also demonstrated

  开发地球上资源丰富、可重复使用和无毒的多相催化剂，用于制药行业的生物活性相关化合物合成仍然是一般化学研究的重要目标。N-甲基化化合物作为最重要的生物活性化合物之一，已广泛应用于精细化工和大宗化工行业，用于生产高价值化学品。在此，首次开发了一种环保且简化的石墨烯包覆 Ni/NiO 纳米合金催化剂（Ni/NiO@C）的制备方法，用于高选择性合成N-在易于处理和工业适用条件下使用各种功能性胺和醛的甲基化化合物。大量的伯胺和仲胺（70多个例子）在不同官能醛的参与下可以转化为相应的N，N-二甲胺，平均收率超过95%。与基准测试相比，克级合成也显示出类似的产量。此外，进一步证明该催化剂由于其固有的磁性而易于回收，并可重复使用多达 10 次而不会失去其活性和选择性。此外，首次串联合成了N , N-二甲胺产品在一锅法中，仅使用一种地球丰富的金属催化剂，其活性和选择性分别超过 99% 和 94%，对于所有测
• Synthesis and antimalarial activity of new analogues of amodiaquine
  作者：Sandrine Delarue-Cochin、Emilia Paunescu、Louis Maes、Elisabeth Mouray、Christian Sergheraert、Philippe Grellier、Patricia Melnyk

  DOI：10.1016/j.ejmech.2007.03.008

  日期：2008.2

  In order to determine the real significance of the 4'-phenolic group in the antimalarial activity and/or cytotoxicity of amodiaquine (AQ), analogues for which this functionality was shifted or modified were synthesized. Good in vitro antimalarial activity was obtained for compounds unable to form intramolecular hydrogen bond. Among the compounds synthesized, new amino derivative 5 displayed the greatest

  为了确定4'-酚基在氨二喹（AQ）的抗疟活性和/或细胞毒性中的真正意义，合成了对其功能进行了转移或修饰的类似物。对于无法形成分子内氢键的化合物，其体外抗疟活性良好。在合成的化合物中，新的氨基衍生物5对测试的对CQ耐药性最高的菌株表现出最大的选择性指数，并且在感染了伯氏疟原虫的小鼠中具有活性。
• Design, synthesis, and biological evaluation of acetophenone derivatives as dual binding acetylcholinesterase inhibitors
  作者：Shen, Yanhong、Li, Baoli、Xu, Hu、Zhang, Guoqiang

  DOI：10.1691/ph.2013.2839

  日期：——

  As part of a project aimed at developing new agents for potential application in Alzheimer's disease, a new series of acetophenone derivatives which possess alkylamine side chains were designed, synthesized and assayed as acetylcholinesterase (AChE) inhibitors that could simultaneously bind to the peripheral and catalytic sites of the enzyme. The compounds were synthesized, and the inhibitory activities toward AChE and butyrylcholinesterase (BuChE) in vitro were determined using a modified Ellman method. Of the compounds tested, 6 derivatives were found to inhibit AChE in the micromolar range. The best compound, 2e, had an IC50 of 0.13 μM. A detailed molecular modeling study was performed to explore the interaction of 2e with AChE.

  作为一个旨在开发阿尔茨海默病潜在应用新药的项目，设计、合成并评估了一系列具有烷基胺侧链的乙酰苯酮衍生物，作为能同时结合酶的外周位点和催化位点的乙酰胆碱酯酶（AChE）抑制剂。这些化合物被合成，并使用改良的埃尔曼法确定其对AChE和丁酰胆碱酯酶（BuChE）的抑制活性。在测试的化合物中，发现有6种衍生物在微摩尔范围内抑制了AChE。最佳化合物2e的IC50为0.13 μM。进行了详细的分子建模研究，以探讨2e与AChE的相互作用。
• 二芳醚类化合物及其制备方法和应用
  申请人：北京大学深圳研究生院

  公开号：CN109134336B

  公开（公告）日：2021-08-03

  本发明涉及一种二芳醚类化合物及其制备方法和应用，该二芳醚类化合物具有如下结构式：其中，‑X‑为‑CH‑或‑N‑；‑R1、‑R2、‑R3分别独立选自‑H、‑F、‑Cl、‑Br、烷氧基、芳基、芳氧基、N,N‑二烷基氨基、N‑烷基‑N‑酰基氨基、吡啶基、咪唑基、吡唑基、呋喃基、吡咯基、吗啉基、N‑烷基哌嗪基、哌啶基和四氢吡咯基中的一种。上述二芳醚类化合物能够抑制肿瘤细胞中PFKFB3的活性，有效阻断的糖酵解过程中关键酶的激活，从而从肿瘤细胞的能量源头阻断其能量供给，为肿瘤疾病的有效治疗提供了一个新的药物。