N-(4-methoxybenzyl)-N-methylcyclohexanamine | 92725-40-1

• 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: N-(4-methoxybenzyl)-N-methylcyclohexanamine
• 英文别名: N-(4-methoxybenzyl)-N-methylcyclohexylamine；N-Methyl-N-(4-methoxy-benzyl)-cyclohexylamin；Cambridge id 5420853；N-[(4-methoxyphenyl)methyl]-N-methylcyclohexanamine
• CAS: 92725-40-1
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: WSLKNVRSFWMKGL-UHFFFAOYSA-N

物化性质

• 沸点：
  328.1±17.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-methoxybenzyl)-N-methylcyclohexanamine 在 1,1,2-三氯乙烷 、 10% palladium on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以98%的产率得到N-甲基环己胺盐酸盐
  参考文献：
  名称：

  Highly Chemoselective Pd−C Catalytic Hydrodechlorination Leading to the Highly Efficient N-Debenzylation of Benzylamines

  摘要：

  In the presence of 1,1,2-trichloroethane, a novel procedure for the Pd-C catalytic N-debenzylation of benzylamines was established. The method proceeded in a synergistic catalytic system and directly gave the products as crystal amine hydrochlorides in practically quantitative yields.

  DOI：

  10.1021/jo9007282
• 作为产物：
  描述：

  N-甲基环己胺 在 palladium diacetate 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 69.0h， 生成 N-(4-methoxybenzyl)-N-methylcyclohexanamine
  参考文献：
  名称：

  Reinvestigation of Aminomethyltrifluoroborates and Their Application in Suzuki−Miyaura Cross-Coupling Reactions

  摘要：

  A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.

  DOI：

  10.1021/jo2001066

文献信息

• Scope of Aminomethylations via Suzuki−Miyaura Cross-Coupling of Organotrifluoroborates
  作者：Gary A. Molander、Paul E. Gormisky、Deidre L. Sandrock

  DOI：10.1021/jo800183q

  日期：2008.3.1

  previously reported the Suzuki−Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to excellent yields to give N,N-dialkylbenzylic amines. The aminomethylation of alkenyl bromides was also examined.

  我们先前报道了N，N-二烷基氨基甲基三氟硼酸酯与芳基溴化物的Suzuki-Miyaura反应。本文中，我们报告了对该钯催化的氨基甲基化反应的范围和局限性的进一步研究。芳基氯化物，碘化物和三氟甲磺酸酯以良好至优异的收率偶联，得到N，N-二烷基苄基胺。还检查了烯基溴化物的氨基甲基化。
• Simplified Version of the Eschweiler–Clarke Reaction
  作者：Klim O. Biriukov、Evgeniya Podyacheva、Ignatii Tarabrin、Oleg I. Afanasyev、Denis Chusov

  DOI：10.1021/acs.joc.3c02476

  日期：2024.3.1

  The traditional Eschweiler–Clarke reaction is a three-component process involving formaldehyde, amine, and formic acid. In this work, we showed that the reductive potential of formaldehyde was sufficient to provide methylation of secondary amines in the absence of acidic additives. Various acid-sensitive moieties remain intact under developed conditions. The scalability of the elaborated approach was

  传统的埃施韦勒-克拉克反应是一个三组分过程，涉及甲醛、胺和甲酸。在这项工作中，我们表明，在没有酸性添加剂的情况下，甲醛的还原电位足以提供仲胺的甲基化。各种酸敏感部分在发达条件下保持完整。多种产品都展示了精心设计的方法的可扩展性。抗真菌剂布替萘芬的合成证明了所开发方法的制备效用。
• SUBSTITUTED BENZENE COMPOUNDS
  申请人：Epizyme, Inc.

  公开号：EP3022184B1

  公开（公告）日：2017-09-27