2,4-二甲基-6-(哌啶-1-基甲基)苯酚 | 55136-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 2,4-二甲基-6-(哌啶-1-基甲基)苯酚
• 英文名称: 2,4-dimethyl-6-(piperidine-1-yl-methyl)phenol
• 英文别名: 2,4-dimethyl-6-(piperidin-1-ylmethyl)phenol；2-(N-piperidinylmethyl)-4,6-dimethylphenol；2,4-Dimethyl-6-piperidinomethyl-phenol；2-(piperidinomethyl)-4,6-dimethylphenol
• CAS: 55136-97-5
• 化学式: C₁₄H₂₁NO
• mdl: MFCD24388171
• 分子量: 219.327
• InChiKey: FOIAJFYKIVQLFT-UHFFFAOYSA-N

物化性质

• 沸点：
  322.7±37.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-二甲基-6-(哌啶-1-基甲基)苯酚 在 三正丁基氢锡 作用下， 反应 0.5h， 以90%的产率得到2,4,6-三甲酚
  参考文献：
  名称：

  Chao, Herbert S.-I., Synthetic Communications, 1988, vol. 18, # 11, p. 1207 - 1212

  摘要：

  DOI：
• 作为产物：
  描述：

  二哌啶甲烷 、 2,4-二甲基苯酚 在 二氧化硫 作用下， 以 乙腈 为溶剂， 反应 42.0h， 以68%的产率得到2,4-二甲基-6-(哌啶-1-基甲基)苯酚
  参考文献：
  名称：

  The activation of aminals and aminol ethers by sulfur dioxide and their reactions with electron rich aromatic compounds

  摘要：

  Reactions of bis(dialkylamino)methanes and ethoxydialkylaminomethanes with nucleophilic aromatic heterocycles in the presence of sulfur dioxide result in the formation of the expected Mannich bases in good yields. Reactions of phenols are similarly activated by sulfur dioxide which lead to improved regioselectivity: in particular the reactions of 2,5-dimethylphenol result in the formation of 2-dialkylaminomethyl-3,6-dimethylphenol whereas reaction occurs at the 4-position using the classical procedures. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00848-x

文献信息

• Rhenium-Catalyzed Dehydrogenative Coupling of Alcohols and Amines to Afford Nitrogen-Containing Aromatics and More
  作者：Matthias Mastalir、Mathias Glatz、Ernst Pittenauer、Günter Allmaier、Karl Kirchner

  DOI：10.1021/acs.orglett.9b00034

  日期：2019.2.15

  An efficient synthesis of quinolines, pyrimidines, quinoxalines, pyrroles, and aminomethylated aromatic compounds catalyzed by a well-defined Re(I) PNP pincer complex is described. All reactions proceed with liberation of dihydrogen and elimination of water. Under optimized reaction conditions a wide range of organic functional groups are tolerated. This study demonstrates that rhenium catalysts are

  描述了由明确定义的Re（I）PNP钳形配合物催化的喹啉，嘧啶，喹喔啉，吡咯和氨基甲基化芳族化合物的有效合成。所有反应均以释放二氢和除去水进行。在优化的反应条件下，可以耐受各种有机官能团。这项研究表明，与类似的Mn（I）配合物相比，rh催化剂在脱氢过程中的表现非常好，催化剂的负载量更低，反应时间更短。
• Manganese-Catalyzed Aminomethylation of Aromatic Compounds with Methanol as a Sustainable C1 Building Block
  作者：Matthias Mastalir、Ernst Pittenauer、Günter Allmaier、Karl Kirchner

  DOI：10.1021/jacs.7b05253

  日期：2017.7.5

  well-defined hydride Mn(I) PNP pincer complex, recently developed in our laboratory, catalyzes this process in a very efficient way, and a total of 28 different aminomethylated products were synthesized and isolated yields of up to 91%. In a preliminary study, a related Fe(II) PNP pincer complex was shown to catalyze the methylation of 2-naphtol rather than its aminomethylation displaying again the divergent

  该研究代表了锰催化的环境良性、实用的三组分氨甲基化活化芳香化合物的第一个例子，包括萘酚、苯酚、吡啶、吲哚、咔唑和噻吩，结合胺和甲醇作为 C1 源。这些反应通过一系列脱氢和缩合步骤以高原子效率进行，从而产生选择性的 CC 和 CN 键形成，从而释放氢和水。我们实验室最近开发了一种明确定义的氢化物 Mn(I) PNP 钳形复合物，以非常有效的方式催化了这一过程，总共合成了 28 种不同的氨甲基化产物，分离产率高达 91%。在初步研究中，
• New Mannich base ligands
  作者：JH Hodgkin

  DOI：10.1071/ch9842371

  日期：——

  A series of low-molecular-weight aminomethylphenol compounds have been synthesized as model analogues of new Cu2+ and Fe3+ chelating polymers. Preliminary colour tests with these two ions were used to indicate the structural features essential for polymer chelate formation.

  一系列 一系列低分子量的氨基甲基苯酚化合物 作为新型 Cu2+ 和 Fe3+ 螯合聚合物的模型类似物被合成出来。 螯合聚合物。用这两种离子进行初步颜色测试 用这两种离子进行的初步颜色测试表明了形成聚合物螯合物所必需的结构特征。 聚合物螯合物形成所必需的结构特征。
• Syntheses of Mononuclear and Dinuclear Aluminum Complexes Stabilized by Phenolato Ligands and Their Applications in the Polymerization of ε-Caprolactone: A Comparative Study
  作者：Lijuan Chen、Wenyi Li、Dan Yuan、Yong Zhang、Qi Shen、Yingming Yao

  DOI：10.1021/acs.inorgchem.5b00022

  日期：2015.5.18

  5 equiv of AlEt3 led to the isolation of mononuclear monoalkyl complexes AlEt[NO]22 (12) and AlEt[NO]32 (13), respectively. All complexes have been characterized by elemental analysis and NMR spectroscopy, and the solid state structures of 5 complexes have been determined by X-ray diffraction analysis. The activities of both binuclear and mononuclear aluminum complexes in initiating the ring-opening

  已经通过烷烃消除反应制备了一系列由酚基配体稳定的单核和双核烷基铝配合物。哌嗪桥双（酚）C 4 H 8 N 2 [1,4-（2-OH-3,5-Me 2 -C 6 H 2 CH 2）2 ]（H 2 [ONNO] 1）的处理，C 4 H 8 N 2 [1,4-（2-OH-3- t Bu-5-Me-C 6 H 2 CH 2）2 ]（H 2 [ONNO] 2）和C 4 H8 N 2 [1,4-（2-OH-3,5- t Bu 2 -C 6 H 2 CH 2）2 ]（H 2 [ONNO] 3）和2.5-3当量的AlR 3（R = Me等）得到双核铝络合物（AlMe 2）2 [ONNO] 1（1），（AlMe 2）2 [ONNO] 2（2），（AlMe 2）2 [ONNO] 3（3），（AlEt 2）2 [ONNO]1（4），（AlEt 2）2 [ONNO] 2（5）和（AlEt 2）2 [ONNO] 3
• A Comparative Study on Dinuclear and Mononuclear Aluminum Methyl Complexes Bearing Piperidyl–Phenolato Ligands in ROP of Epoxides
  作者：Wenyi Li、Hao Ouyang、Lijuan Chen、Dan Yuan、Yong Zhang、Yingming Yao

  DOI：10.1021/acs.inorgchem.6b00639

  日期：2016.7.5

  Dinuclear aluminum methyl complexes stabilized by piperidyl–phenolato ligands were prepared and characterized. The ring-opening polymerizations of cyclohexene oxide (CHO) and propylene oxide (PO) initiated by dinuclear complexes and mononuclear analogues were investigated and compared. Enhanced activity of dinuclear complexes compared to that of mononuclear analogues in both the ring-opening polymerization

  制备并表征了由哌啶基-苯酚基配体稳定的双核甲基铝配合物。研究并比较了由双核配合物和单核类似物引发的环己烯氧化物（CHO）和环氧丙烷（PO）的开环聚合反应。在CHO和PO的开环聚合中，与单核类似物相比，双核复合物的活性增强，证明了前者中两个Al中心的协同相互作用。通过MALDI-TOF质谱对低聚物进行的端基分析证实了甲基作为引发基团的作用。提出了一种双金属机理，其中两个铝中心的合作参与了聚合过程。