1-(4-methylphenyl)-N-(2,4,4-trimethylpentan-2-yl)methanimine | 1351379-05-9

• 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: 1-(4-methylphenyl)-N-(2,4,4-trimethylpentan-2-yl)methanimine
• CAS: 1351379-05-9
• 化学式: C₁₆H₂₅N
• 分子量: 231.381
• InChiKey: VDFLSBUTVHCBFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  叔辛胺 、 (4-甲基苯基)甲醇 在 三乙烯二胺 、 [RuCl₂(IiPr)(p-cymene)] 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以77%的产率得到1-(4-methylphenyl)-N-(2,4,4-trimethylpentan-2-yl)methanimine
  参考文献：
  名称：

  Dehydrogenative Synthesis of Imines from Alcohols and Amines Catalyzed by a Ruthenium N-Heterocyclic Carbene Complex

  摘要：

  A new method for the direct synthesis of imines from alcohols and amines is described where hydrogen gas is liberated. The reaction is catalyzed by the ruthenium N-heterocyclic carbene complex [RuCl2(IiPr)(p-cymene)] in the presence of the ligand DABCO and molecular sieves. The imination can be applied to a variety of primary alcohols and amines and can be combined with a subsequent addition reaction. A deuterium labeling experiment indicates that the catalytically active species is a ruthenium dihydride. The reaction is believed to proceed by initial dehydrogenation of the alcohol to the aldehyde, which stays coordinated to ruthenium. Nucleophilic attack of the amine affords the hemiaminal, which is released from ruthenium and converted into the imine.

  DOI：

  10.1021/om201095m

文献信息

• A Metalloenzyme-Like Catalytic System for the Chemoselective Oxidative Cross-Coupling of Primary Amines to Imines under Ambient Conditions
  作者：Martine Largeron、Maurice-Bernard Fleury

  DOI：10.1002/chem.201405843

  日期：2015.2.23

  This homogeneous cooperative catalytic system has been inspired by the reaction of copper amine oxidases, a family of metalloenzymes with quinone organic cofactors that mediate the selective oxidation of primary amines to aldehydes. After optimization, the desired cross‐coupled imines are obtained in high yields with broad substrate scope through a transamination process that leads to the homocoupled

  伯胺的直接氧化交叉偶联是一项具有挑战性的转化，因为通常首选均相偶联。通过铜的低负荷的协同组合，我们在此报告交叉耦合亚胺的化学选择性制备II金属催化剂和ö亚氨基醌有机催化剂在环境条件下。这种均相的协同催化体系的灵感来自铜胺氧化酶的反应，铜胺氧化酶是金属酶家族与介导伯胺选择性氧化为醛基的醌有机辅因子的反应。经过优化后，通过转氨过程可实现所需的交叉偶联亚胺，从而获得高收率，具有广泛的底物范围，该过程导致均偶联亚胺中间体，然后进行动态氨基转移。从环境的观点来看，在室温下并且在环境空气而不是分子氧作为氧化剂的情况下进行反应的能力以及等摩尔量的每种偶联配偶体是特别有吸引力的。
• Dehydrogenative Synthesis of Imines from Alcohols and Amines Catalyzed by a Ruthenium N-Heterocyclic Carbene Complex
  作者：Agnese Maggi、Robert Madsen

  DOI：10.1021/om201095m

  日期：2012.1.9

  A new method for the direct synthesis of imines from alcohols and amines is described where hydrogen gas is liberated. The reaction is catalyzed by the ruthenium N-heterocyclic carbene complex [RuCl2(IiPr)(p-cymene)] in the presence of the ligand DABCO and molecular sieves. The imination can be applied to a variety of primary alcohols and amines and can be combined with a subsequent addition reaction. A deuterium labeling experiment indicates that the catalytically active species is a ruthenium dihydride. The reaction is believed to proceed by initial dehydrogenation of the alcohol to the aldehyde, which stays coordinated to ruthenium. Nucleophilic attack of the amine affords the hemiaminal, which is released from ruthenium and converted into the imine.