4-乙基-3,5-二甲氧基-苯胺 | 78025-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-乙基-3,5-二甲氧基-苯胺
• 英文名称: 4-ethyl-3,5-dimethoxy-aniline
• 英文别名: 4-Aethyl-3,5-dimethoxy-anilin；4-Ethyl-3,5-dimethoxyaniline
• CAS: 78025-97-5
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: UMGYOVPTMJBRJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-乙基-3,5-二甲氧基-苯胺 在 镍 甲酸 、 Cu₂(CN)2 、 氰化钠 、 potassium tert-butylate 、 亚硝酸 作用下， 以 水 、 二甲基亚砜 、 叔丁醇 为溶剂， 反应 9.0h， 生成 3-anilino-2-(4-ethyl-3,5-dimethoxybenzyl)acrylonitrile
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 5. 3',5'-Dimethoxy-4'-substituted-benzyl analogs of trimethoprim

  摘要：

  Forty trimethoprim analogues in which the para substituent in the benzene ring was varied were prepared for antibacterial evaluation. All were very potent inhibitors of Escherichia coli dihydrofolate reductase. The similarity of their inhibitory activities strongly suggested that the side chains beyond the first two atoms were not in contact with the enzyme. However, among 38 ether derivatives which varied widely in their bulk and lipophilicity, very few approached trimethoprim in their broad-spectrum in vitro antibacterial activity. The 4'-methyl and 4'-ethyl analogues and the allyloxy and gamma-chloropropoxy ethers had activities fairly close to that of trimethoprim. The two ethers were chosen for further evaluation in vivo. Neither compound quite matched trimethoprim in efficacy in mice, and their half-lives, as well as that of the beta-methoxyethoxy analogue, were found to be shorter in dogs.

  DOI：

  10.1021/jm00140a005
• 作为产物：
  描述：

  2,6-二甲氧基苯乙酮 在 palladium on activated charcoal 1,4-二氧六环 、 氨 、 氢气 、 溴 、 ferric nitrate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 3.5h， 生成 4-乙基-3,5-二甲氧基-苯胺
  参考文献：
  名称：

  2,4-Diamino-5-benzylpyrimidines and analogs as antibacterial agents. 5. 3',5'-Dimethoxy-4'-substituted-benzyl analogs of trimethoprim

  摘要：

  Forty trimethoprim analogues in which the para substituent in the benzene ring was varied were prepared for antibacterial evaluation. All were very potent inhibitors of Escherichia coli dihydrofolate reductase. The similarity of their inhibitory activities strongly suggested that the side chains beyond the first two atoms were not in contact with the enzyme. However, among 38 ether derivatives which varied widely in their bulk and lipophilicity, very few approached trimethoprim in their broad-spectrum in vitro antibacterial activity. The 4'-methyl and 4'-ethyl analogues and the allyloxy and gamma-chloropropoxy ethers had activities fairly close to that of trimethoprim. The two ethers were chosen for further evaluation in vivo. Neither compound quite matched trimethoprim in efficacy in mice, and their half-lives, as well as that of the beta-methoxyethoxy analogue, were found to be shorter in dogs.

  DOI：

  10.1021/jm00140a005

文献信息

• Novel and Highly Regioselective Friedel-Crafts Alkylation of 3,5-Dimethoxy­aniline Using an Aldehyde and Triethylsilane as Reducing Agent
  作者：John Augustine、Yanjerappa Naik、Ashis Mandal、Padma Alagarsamy、Vani Akabote

  DOI：10.1055/s-2008-1078207

  日期：——

  regioselective Friedel-Crafts alkyl- ation, producing p-alkyl 3,5-dimethoxyanilines by the reaction of aldehydes with 3,5-dimethoxyaniline in the presence of trifluoro- acetic acid and triethylsilane as reducing agent is reported. This pro- cedure is lauded by its high regioselectivity, simplicity, and adaptability to aromatic, heteroaromatic, and aliphatic aldehydes. This reaction represents a useful

  报道了一种新型且高度区域选择性的 Friedel-Crafts 烷基化反应，通过醛与 3,5-二甲氧基苯胺在三氟乙酸和三乙基硅烷作为还原剂的存在下反应生成对烷基 3,5-二甲氧基苯胺。该方法因其高区域选择性、简单性以及对芳香族、杂芳香族和脂肪族醛的适应性而受到称赞。该反应代表了一种有用的方法来制备各种具有潜在药理学意义的 4-取代的 3,5-二甲氧基苯胺。
• A Dynamic Kinetic Resolution Approach to Axially Chiral Diaryl Ethers by Catalytic Atroposelective Transfer Hydrogenation
  作者：Linlong Dai、Yuheng Liu、Qing Xu、Meifang Wang、Qiaohong Zhu、Peiyuan Yu、Guofu Zhong、Xiaofei Zeng

  DOI：10.1002/anie.202216534

  日期：2023.2.6

  A dynamic kinetic resolution approach was developed for the synthesis of axially chiral diaryl ethers via a Brønsted acid catalyzed atroposelective transfer hydrogenation (ATH) reaction of dicarbaldehydes with anilines. The chiral phosphoric acid catalyzed dynamic kinetic resolution strategy has provided a modular platform for the synthesis of axially chiral diaryl ethers.

  开发了一种动态动力学拆分方法，用于通过 Brønsted 酸催化二甲醛与苯胺的逆向选择性转移氢化 (ATH) 反应合成轴向手性二芳基醚。手性磷酸催化的动态动力学拆分策略为轴向手性二芳基醚的合成提供了模块化平台。
• Richtzenhain; Nippus, Chemische Berichte, 1949, vol. 82, p. 408,414
  作者：Richtzenhain、Nippus

  DOI：——

  日期：——
• ROTH, B.;AIG, E.;RAUCKMAN, B. S.;STRELITZ, J. Z.;PHILLIPS, A. P.;FERONE, +, J. MED. CHEM., 1981, 24, N 8, 933-941
  作者：ROTH, B.、AIG, E.、RAUCKMAN, B. S.、STRELITZ, J. Z.、PHILLIPS, A. P.、FERONE, +

  DOI：——

  日期：——
• AZOARYLS AS REVERSIBLY MODULATABLE TUBULIN INHIBITORS
  申请人：ECOLE NORMALE SUPERIEURE DE LYON

  公开号：US20170051149A1

  公开（公告）日：2017-02-23

  The invention concerns a new class of tubulin polymerisation inhibitors and their applications in research and medicine, notably in chemotherapy. The invention proposes new azoaryl derivatives of formula (I): as defined in Claim 1 , which may be fully reversibly interconverted between non-tubulin-binding trans and tubulin-binding as isomeric forms, either by irradiation or spontaneously. The invention also concerns compounds with a azoaryl structure for use in studying the cytoskeleton and/or its associated processes, or in the treatment of a disease for which a tubulin polymerisation inhibition activity has a beneficial effect, wherein the compound is administered to the cell, organism or patient in need of such treatment in the trans form of the diazenyl bond, and where this trans form is inactive as regards a tubulin polymerisation inhibition effect, and where after photoisomerisation in vitro, in cellulo or in vivo to an azoaryl compound in its cis isomeric form of the diazenyl bond by the application of light, optionally with modification in vitro, in cellulo or in vivo of one or more substituents, the resultant cis form is active as regards a tubulin polymerisation inhibition effect.