2-(N,N-dimethylaminomethyl)-6-tert-butylphenol | 64325-12-8

• 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: 2-(N,N-dimethylaminomethyl)-6-tert-butylphenol
• 英文别名: HOC6H3(CH2NNe2)-2-t-Bu-6；2-CH2NMe2-6-tBu-C6H3OH；Phenol, 2-[(dimethylamino)methyl]-6-(1,1-dimethylethyl)-；2-tert-butyl-6-[(dimethylamino)methyl]phenol
• CAS: 64325-12-8
• 化学式: C₁₃H₂₁NO
• 分子量: 207.316
• InChiKey: KYSKKDIVJXOZGP-UHFFFAOYSA-N

物化性质

• 沸点：
  60 °C(Press: 0.005 Torr)
• 密度：
  0.981±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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-(N,N-dimethylaminomethyl)-6-tert-butylphenol 在 palladium (4%) on activated charcoal 、 氢气 作用下， 130.0 ℃ 、5.0 MPa 条件下， 反应 11.0h， 以95%的产率得到2-叔丁基-6-甲基苯酚
  参考文献：
  名称：

  About selective methods of synthesis of 6-tert-butyl-2-methylphenol and 6-tert-butyl-2,4-dimethylphenol

  摘要：

  Vapor phase catalytic methylation with methanol of 2-tert-butylphenol at the temperature 280-300A degrees C proceeds selectively with formation of 6-tert-butyl-2-methylphenol. Elevating reaction temperature above 300A degrees C leads to formation of 2,6-dimethylphenol. Reaction of 2-tert-butylphenol with methanol in alkaline medium in the presence of zinc oxide is shown to lead initially to formation of a mixture of calixarenes and methylenebisphenols that at elevated temperature exert splitting leading in future to 6-tert-butyl-2,4-dimethylphenol. Obtaining it in this reaction from 2,2'-methylenebis-(6-tert-butyl-4-methylphenol) proceeds selectively. Pathways of the reductive methylation of methylenebisphenols with methanol in alkaline medium is considered.

  DOI：

  10.1134/s1070363209060218
• 作为产物：
  描述：

  2-叔丁基苯酚 、 n,n-二甲基亚甲基碘化胺 在 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以80%的产率得到2-(N,N-dimethylaminomethyl)-6-tert-butylphenol
  参考文献：
  名称：

  Selective Synthesis of Phenolic Mannich Bases under Solid-Liquid Phase Transfer Conditions

  摘要：

  DOI：

  10.1055/s-1983-30560

文献信息

• Synthesis and Structure of Neutral and Cationic Aluminum Complexes Supported by Bidentate <i>O</i>,<i>P</i>-Phosphinophenolate Ligands and Their Reactivity with Propylene Oxide and ε-Caprolactone
  作者：Mansour Haddad、Mohamed Laghzaoui、Richard Welter、Samuel Dagorne

  DOI：10.1021/om9003362

  日期：2009.8.10

  The O,P-type phosphinophenol ligands 1a−c were found to readily react with 1 equiv of AlMe3 to afford in high yields the corresponding Al chelate complexes η2-O,P-(2-PPh2-4-R′-6-R-C6H2O)}AlMe2, 2a−c (R = Me, R′ = H, 2a; R = Ph, R′ = H, 2b; R = tBu, R′ = Me, 2c). The bis-adduct Al methyl complexes η2-O,P-(2-PPh2-4-R′-6-R-C6H2O)}2AlMe (R = Ph, R′ = H, 3b; R = tBu, R′ = Me, 3c) also formed quantitatively

  发现O，P型膦基苯酚配体1a - c容易与1当量的AlMe 3反应，以高收率提供相应的Al螯合物[ 2 -O，P-（2-PPh 2 -4-R' -6-RC 6 H ^ 2 O）}阿尔梅2，图2a - ç（R = Me中，R'= H，2a中; R =苯基，R'= H，2b中; R =吨卜，R'= Me中，图2c）。的双加合物的Al甲基络合物η 2 -O，P-（2-PPH 2 -4-R'-6-RC 6 H ^ 2 O）} 2AlMe（R = Ph，R'= H，3b ; R = t Bu，R'= Me，3c）在膦基酚1b，c与0.5当量的AlMe 3反应时也定量形成。单加成和双加成Al甲基物质2a - c和3b，c都是稳定的单体形式，无论是在溶液中还是在固态，并且在配位溶剂如thf中均保持稳定。与此相反，双-加合物的Al甲基络合物3c中经历在醇源的存在下进行配位体交换反应（我异丙醇，BnOH）以产生均配型三-加合物的Al复合η
• O,N-Chelated Vanadium(IV) Oxo Aminophenolate Complexes: the Effect of Steric Bulk on the Vanadium Coordination Geometry. Can this Influence be detected Spectroscopically?
  作者：Henk Hagen、Santiago Reinoso、Ed J. Reijerse、Ernst E. van Faassen、Martin Lutz、Anthony L. Spek、Gerard van Koten

  DOI：10.1002/zaac.200400337

  日期：2004.10

  In order to study the effect of steric bulk on the vanadium coordination geometry in O,N-chelated vanadium oxo (bis)phenol- ates, six different ortho-aminophenolate ligands have been used. The ortho-aminophenolate system was changed at three different places, i.e. 1) the second ortho position (C 6 ) of the arene ring (R), 2) the substituents at the amino nitrogen (R and R), and 3) the benzylic carbon

  为了研究空间体积对 O,N 螯合的氧代（双）酚酸钒中钒配位几何结构的影响，使用了六种不同的邻氨基酚盐配体。邻氨基苯酚盐体系在三个不同的位置发生了变化，即 1) 芳烃环 (R) 的第二个邻位 (C 6 )，2) 氨基氮上的取代基 (R 和 R)，以及 3) 苄基碳原子 (R * )。酚类用于制备氧代（双）酚钒络合物。为了研究是否可以预测几何特征
• Synthesis and Structural Characterization of Neutral and Cationic Alkylaluminum Complexes Based on Bidentate Aminophenolate Ligands
  作者：Samuel Dagorne、Laurent Lavanant、Richard Welter、Christophe Chassenieux、Pierre Haquette、Gérard Jaouen

  DOI：10.1021/om0302185

  日期：2003.9.1

  cation 3a+, as determined by X-ray crystallography analysis for 3b‘+ and 2D NMR studies for 3a+ and 3c,d+/3c‘,d‘+. All the formed dinuclear cations are quite stable and robust in solution, and no fluxional behavior for any of them was observed up to 80 °C in C6D5Br. Cations 3b−d+/3b‘−d‘+ react with a Lewis base such as THF to afford the corresponding THF adduct cation 4b−d+ along with 1 equiv of the corresponding

  氨基苯酚2-（CH的反应2 L）-6-RC 6 H ^ 3 OH（R =苯基，L = NME 2，1A ; R =吨卜，L = NME 2，1B ; R =吨卜，L = NC 4 ħ 8，1C ; R =吨卜，L = NC 5 H ^ 10，1D）与1个当量的阿尔梅3分得到相应的二甲基铝络合物2-（CH 2 L）-6-RC 6 H ^ 3 ö}阿尔梅2（R =苯基，L = NME 2，图2a ; R =吨卜，L = NME 2，2B ; R =吨卜，L = NC 4 ħ 8，图2c ; R =吨卜，L = NC 5 H ^ 10，2D）以高产率。基于对2b，d的X射线分析和对于2a - d的NMR数据，化合物2a - d似乎是单体的，并且在THF的存在下是稳定的。2-（CH 2 NMe 2）-6-Ph-C 6 H 3 O} AlMe 2（2a）与B（C 6 F 5）3干净反应，生成双核阳离子Al
• Modular synthesis of spirocyclic carbonates: unravelling the synergistic interplay of electronic and electrostatic sites on phenolic catalyst
  作者：Shilpa Dabas、Brijesh Patel、Sanjay Mehra、Manas Barik、Prabhahar Murugan、Arvind Kumar、Saravanan Subramanian

  DOI：10.1039/d3gc03989g

  日期：——

  Spirocyclic carbonates: A simple and efficient organocatalytic approach for the chemical fixation of CO₂ with spiroepoxy oxindoles has been demonstrated. The catalytic protocol may provide additional possibilities to new applications.

  螺环碳酸盐：研究证明了一种简单高效的有机催化方法，可将二氧化碳与螺环氧吲哚进行化学固定。该催化方案可为新应用提供更多可能性。
• Salakhutdinov, N. F.; Krysin, A. P.; Koptyug, V. A., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 4, p. 664 - 665
  作者：Salakhutdinov, N. F.、Krysin, A. P.、Koptyug, V. A.

  DOI：——

  日期：——