N-(3,4-dimethoxybenzylidene)methanamine | 17972-14-4

• 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-dimethoxybenzylidene)methanamine
• 英文别名: 3,4-dimethoxybenzylidene-N-methylamine；3,4-dimethoxybenzylidenemethylamine；methyl-veratryliden-amine；Methyl-veratryliden-amin；N-<3,4-Dimethoxy-benzyliden>-methylamin；3,4-Dimethoxybenzaldehyd-methylimin；Methanamine, N-[(3,4-dimethoxyphenyl)methylene]-；1-(3,4-dimethoxyphenyl)-N-methylmethanimine
• CAS: 17972-14-4
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: KEXUHJWIXIKGOS-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57 °C
• 沸点：
  145 °C(Press: 11 Torr)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethoxybenzylidene)methanamine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 苯,1,2-二甲氧基-4-[2-(4-甲氧苯基)乙烯基]-,(E)-
  参考文献：
  名称：

  1,2-二氢异喹啉—XX：重排—VI

  摘要：

  DOI：

  10.1016/0040-4020(75)80059-7
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 硫酸羟胺 、 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 生成 N-(3,4-dimethoxybenzylidene)methanamine
  参考文献：
  名称：

  10.1134/s003602442403035x

  摘要：

  DOI：

  10.1134/s003602442403035x

文献信息

• A telescopic one-pot synthesis of β-lactam rings using amines as a convenient source of imines
  作者：Suvi H. M. Rajamäki、Lidia De Luca、Francesca Capitta、Andrea Porcheddu

  DOI：10.1039/c6ra02744j

  日期：——

  A facile synthetic approach to substituted β-lactams was designed, using secondary benzylic amines and acid chlorides as starting materials. The reactions proceeded smoothly and all the products were obtained in good yields.

  以仲苄胺和酰氯为起始原料，设计了一种简便的合成取代β-内酰胺的方法。反应进行顺利，所有产物均以高收率获得。
• A Novel Construction of 2-Benzazepine Scaffold Based on TiCl4-Mediated Tandem Mannich Reaction–Aromatic Electrophilic Substitution
  作者：Liangxi Li、Zhiming Li、Quanrui Wang

  DOI：10.1002/hlca.200900107

  日期：2009.12

  A novel construction of 2‐benzazepine derivatives based on TiCl4‐mediated tandem Mannich reaction of electron‐rich benzyl iminium ions with alkenyl ethers and Friedel–Crafts‐type alkylation is described. The protocol is amenable to provide the tricyclic furo[3,2‐d][2]benzazepine and pyrano[3,2‐d][2]benzazepine derivatives, respectively, with 2,3‐dihydrofuran or 3,4‐dihydro‐2H‐pyran as the substrates

  描述了一种基于TiCl 4介导的富电子苄基亚胺离子与链烯基醚和Friedel – Crafts型烷基化的串联曼尼希反应的新型2-苯并ze庚因衍生物的结构。该协议适用于分别为三环呋喃[3,2- d ] [2]苯并and庚因和吡喃并[3,2- d ] [2]苯并ze庚因衍生物提供2,3-二氢呋喃或3,4-二氢呋喃。 2 H-吡喃为底物。
• 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。
• A New Synthetic Approach to Dioxoaporphines − Application to the Synthesis of N-Methylouregidione
  作者：Christophe Hoarau、Axel Couture、Eric Deniau、Pierre Grandclaudon

  DOI：10.1002/1099-0690(200107)2001:13<2559::aid-ejoc2559>3.0.co;2-3

  日期：2001.7

  A convenient and versatile short-step synthesis of dioxoaporphines, illustrated by the first total synthesis of the alkaloid N-methylouregidione (1c), is described.

  描述了二氧杂卟啉的一种方便且通用的短步合成方法，以生物碱N-甲基尿嘧啶酮（1c）的第一次全合成为例。
• 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。