2-甲氧基-4-[(甲基亚胺)甲基]苯酚 | 84145-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-甲氧基-4-[(甲基亚胺)甲基]苯酚
• 英文名称: 2-Methoxy-4-[(methylimino)methyl]phenol
• 英文别名: 2-methoxy-4-(methyliminomethyl)phenol
• CAS: 84145-54-0
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: OKYNVMRFOLPHBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2925290090

反应信息

• 作为产物：
  描述：

  香草醛 在 硫酸羟胺 、 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 生成 2-甲氧基-4-[(甲基亚胺)甲基]苯酚
  参考文献：
  名称：

  10.1134/s003602442403035x

  摘要：

  DOI：

  10.1134/s003602442403035x

文献信息

• Simple and efficient one-pot solvent-free synthesis of N-methyl imines of aromatic aldehydes
  作者：Niko S. Radulović、Ana B. Miltojević、Rastko D. Vukićević

  DOI：10.1016/j.crci.2013.01.010

  日期：2013.3

  Résumé A one-pot solvent-free synthesis of N-methyl imines in good to excellent yields was performed by grinding together aromatic aldehydes and methylamine hydrochloride in the presence of a base. The best yields were achieved when an excess of methylamine hydrochloride and inexpensive sodium hydrogen carbonate was used (usually in a molar ratio ArCHO/CH3NH2·HCl/NaHCO3 = 1:5:5), allowing the reaction to proceed for 1 h (in the case of aromatic aldehydes containing electron-withdrawing substituents) or overnight (in the case of electron-rich aldehydes). After a simple work-up (extraction with diethyl ether) the obtained products were mostly pure enough for spectral characterization. In this way, 31 N-methyl imines were prepared, among which eight were synthesized for the first time. Their structures were elucidated by spectral means (1H- and 13C-NMR, IR, MS) whenever it was possible. In the case of salicylaldehyde and 4-chlorobenzaldehyde, the synthesis of the corresponding imines was also conducted on a gram-scale with a 72% and 84% isolated yield, respectively. The present approach not only provides good to high yields, but also eliminates the disadvantages of the traditional synthesis of N-methyl imines, such as the use of hazardous solvents and more or less expensive catalysts and the necessity of work/handling with an anhydrous gas in pressurized containers.

  简述 在碱存在下，通过将芳香醛和盐酸甲胺研磨在一起，实现了 N-甲基亚胺的单锅无溶剂合成，收率从良好到极佳。当使用过量的盐酸甲胺和廉价的碳酸氢钠时（通常摩尔比 ArCHO/CH3NH2-HCl/NaHCO3 = 1:5:5），让反应进行 1 小时（如果是含有抽电子取代基的芳香醛）或过夜（如果是电子丰富的醛），可获得最佳收率。经过简单的处理（用二乙醚萃取）后，得到的产物大多纯度很高，足以进行光谱鉴定。通过这种方法，共制备出 31 种 N-甲基亚胺，其中 8 种是首次合成。在可能的情况下，通过光谱手段（1H-和 13C-NMR、IR、MS）阐明了它们的结构。对于水杨醛和 4-氯苯甲醛，也在克级规模上合成了相应的亚胺，分离收率分别为 72% 和 84%。本方法不仅产量高，而且消除了传统合成 N-甲基亚胺的缺点，如使用有害溶剂和或多或少昂贵的催化剂，以及必须在加压容器中使用无水气体工作/处理。
• Mechanosynthesis of
  作者：Nader Ghaffari Khaligh、Ong Chiu Ling、Taraneh Mihankhah、Mohd Rafie Johan、Juan Joon Ching

  DOI：10.1071/ch18408

  日期：——

  modified method and its application as an efficient promoter was demonstrated for the mechanosynthesis of N-methyl imines using ball milling as a non-conventional process under solvent-free conditions. In this new protocol design, the bis-imidazole acted as a recyclable acid-scavenging agent. This efficient approach to the N-methyl imines displays a combination of the synthetic virtues of a non-conventional

  通过改进的方法制备了1,1'-（1,4-丁二基）双（咪唑），并证明了其作为有效促进剂在溶剂中采用球磨作为非常规方法机械合成N-甲基亚胺的应用。无条件。在这种新的方案设计中，双咪唑用作可回收的除酸剂。这种高效的方法来Ñ-甲基亚胺显示出非常规缩合反应的合成优点与生态效益和简便的机械合成过程的便利性的组合。当前的方法具有以下优点：通过避免溶剂来减少浪费，在反应过程中排除有害物质，消除了在真空容器中处理无水气体或甲胺在乙醇中的溶液，相对无反应的含有给电子取代基的苯甲醛的产率高的优点。 ，反应时间短以及无金属和无酸条件。此外，该启动子易于再生并重复使用几次，而活性没有明显损失。
• Synthesis of N-methyl imines in the presence of poly(N-vinylpyridine) as a reusable solid base catalyst by a mechanochemical process
  作者：Nader Ghaffari Khaligh、Hanna S. Abbo、Salam J. J. Titinchi

  DOI：10.1007/s11164-016-2672-y

  日期：2017.2

  catalytic amounts of poly(4-vinylpyridine) in high yields and rapidly at room temperature by a ball milling process. This new method has some advantages including good yields for relatively unreactive carbonyl compounds and short reaction times as well as being green in terms of avoiding the use of toxic reagents and solvents. The major advantage of this process is that the catalyst can be easily regenerated

  N- 甲基亚胺的合成 在催化量的聚（4-乙烯基吡啶）的存在下以高收率和通过球磨法在室温下快速进行。该新方法具有一些优点，包括相对不活泼的羰基化合物的高收率和较短的反应时间，并且在避免使用有毒试剂和溶剂方面是绿色的。该方法的主要优点是催化剂可以容易地再生和重复使用几次，而没有任何明显的活性损失。
• 4,4′-Trimethylenedipiperidine, a safe and greener alternative for piperidine, catalyzed the synthesis of N-methyl imines
  作者：Hayedeh Gorjian、Nader Ghaffari Khaligh

  DOI：10.1007/s11164-022-04680-2

  日期：2022.5

  A practical and facile synthesis of various N-methyl imines, versatile scaffolds, was conducted at 85 °C using 4,4′-trimethylenedipiperidine as a safe and green catalyst. This reagent is a commercially available solid and can be handled easily. It has high thermal stability, low toxicity, and good solubility in green solvents such as water and ethanol. The regenerated catalyst demonstrated stable activity

  使用 4,4'-三亚甲基二哌啶作为安全和绿色的催化剂，在 85 °C 下进行了各种N-甲基亚胺、多功能支架的实用且简便的合成。该试剂是一​​种市售固体，易于处理。热稳定性高、毒性低，在水、乙醇等绿色溶剂中溶解性好。再生后的催化剂在多次循环运行后表现出稳定的活性，其化学结构发生任何变化1H 核磁共振监测。目前工作的新颖之处在于，4,4'-三亚甲基二哌啶由于其广泛的液体温度范围、热稳定性、受体/供体氢键性质和其他独特的特性，可以作为哌啶在较高温度下有机反应中的有希望的替代品。优点。此外，目前的协议避免了在处理过程中产生废物，这是大多数以前报告的程序中的一个缺点。
• TOPICAL FORMULATIONS COMPRISING A 1-N-ARYLPYRAZOLE DERIVATIVE AND A FORMAMIDINE
  申请人：Merial, Inc.

  公开号：EP1694123B1

  公开（公告）日：2017-09-06