2-Methoxy-6-{(E)-[(4-methylphenyl)imino]methyl}phenol | 20772-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-Methoxy-6-{(E)-[(4-methylphenyl)imino]methyl}phenol
• 英文别名: 2-methoxy-6-((E)-[(4-methylphenyl)imino]methyl)phenol；(2-hydroxy-3-methoxy-benzylidene)-p-tolyl-amine；2-((E)-(p-tolylimino)methyl)-6-methoxyphenol；2-Methoxy-6-(p-tolylimino-methyl)-phenol；(2-Oxy-3-methoxy-benzal)-p-toluidin
• CAS: 20772-64-9
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: OYEREWRJWMPHMA-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,3-二氢呋喃 、 2-Methoxy-6-{(E)-[(4-methylphenyl)imino]methyl}phenol 在 lithium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以90%的产率得到(3aS,4R,9aR)-8-methoxy-N-(4-methylphenyl)-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromen-4-amine
  参考文献：
  名称：

  LiBF4-catalyzed formation of fused pyrano- and furanobenzopyrans

  摘要：

  Lithium tetrafluoroborate efficiently catalyzes an unusual cyclization of o-hydroxybenzaldimines with 2,3-dihydrofuran and 3,4-dihydro-2H-pyran at ambient temperature to afford a class of new pyrano- and furanobenzopyran derivatives in excellent yields with high diastereo selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01257-6
• 作为产物：
  描述：

  乙烷,三氯氟- 、 邻香草醛 以 乙醇 为溶剂， 反应 1.0h， 以87%的产率得到2-Methoxy-6-{(E)-[(4-methylphenyl)imino]methyl}phenol
  参考文献：
  名称：

  过渡金属配合物的合成与表征：它们的醇氧化和电化学性质

  摘要：

  五个席夫碱配体HA 1，HA 2，H 2 L 1 -H 2 L 3，以及它们的Co（II），Mn（III）和Ru（III）配合物，已经通过分析，光谱，电导，磁矩和电化学研究进行了合成和表征。描述了苄醇氧化为相应的羰基化合物。在某些伯苄醇的情况下，获得了高转化率。仲苄醇（2-羟基-1，2-二苯乙酮衍生物）以令人满意的转化率选择性地转化为相应的酮。在不同的扫描速率和溶剂下都记录了所有配合物的电化学性质。配合物的电化学性质随扫描速率而变化。

  DOI：

  10.1080/15533174.2010.538288

文献信息

• Catalytic investigation of Pd(II) complexes over Heck-Mizoroki reaction: Tailored synthesis, characterization and density functional theory
  作者：Satyendra Shukla、Pratiksha Gaur、Sanjay Bagri、Ripul Mehrotra、Bhaskar Chaurasia

  DOI：10.2298/jsc200902075s

  日期：——

  Tailored reaction of Schiff base ligands with palladium(II) chloride and imidazole afford three complexes of formula [Pd(II)(L)(imdz)2]Cl, which are L = 2-((E)-(p-lylimino)methyl)-6-methoxyphenol (complex 1), 2-methoxy- -6-((E)-(phenylimine)methyl)phenol (complex 2) and 2-((E)-(4-chlorophenylimino) methyl)-6-methoxyphenol (complex 3). Compounds were characterized with elemental analysis, molar conductance, electronic spectroscopy, ESI-MS, FT-IR, TGA, 1H-NMR and 13C-NMR. Molecular structure and different quantum chemical parameters were calculated using the B3LYP basis set of density functional theory with the standard 6-311+G (d, 2p) level. The catalytic potential of 1-3 was examined over Heck-Mizoroki reaction and found in order of 1 > 2 > 3.

  希夫碱配体与氯化钯(II)和咪唑的定制反应产生了三种[Pd(II)(L)(imdz)2]Cl、其中 L = 2-((E)-(对-亚氨基)甲基)-6-甲氧基苯酚（复合物 1）、2-甲氧基-6-((E)-(苯基亚氨基)甲基)苯酚（复合物 2）和 2-((E)-(4-氯苯基亚氨基)甲基)-6-甲氧基苯酚（复合物 3）。化合物的表征包括元素分析、摩尔电导、电子能谱、ESI-MS、傅立叶变换红外光谱、热重分析、1H-NMR 和 13C-NMR 等。采用密度泛函理论的 B3LYP 基集和标准 6-311+G (d, 2p) 水平计算了分子结构和不同的量子化学参数。研究发现，1-3 在 Heck-Mizoroki 反应中的催化潜能依次为 1 > 2 > 3。
• Indium(III) chloride catalyzed in situ generation of enamines and cyclization with imines: a novel route for synthesis of hexahydroxanthene-9-N-arylamines
  作者：Marimuthu Anniyappan、D Muralidharan、Paramasivan T Perumal、Jagadese J Vittal

  DOI：10.1016/j.tet.2004.02.009

  日期：2004.3

  A simple, efficient, and novel method has been developed for the synthesis of hexahydroxanthene-9-N-arylamine derivatives through a one-pot reaction of cyclohexanone and morpholine with salicylaldehyde imines in the presence of indium(III) chloride as a catalyst. 1-(4-Morpholino)-cyclohexene enamine prepared in situ from cyclohexanone and morpholine in presence of 20 mol% InCl3 in acetonitrile under

  已经开发了一种简单，有效和新颖的方法，用于在氯化铟（III）催化剂存在下，通过环己酮和吗啉与水杨醛亚胺的一锅反应，合成六氢氧杂蒽-9 - N-芳基胺衍生物。在回流条件下，由环己酮和吗啉在乙腈中存在20 mol％InCl 3的条件下，由环己酮和吗啉原位制备的1-（4-Morpholino）-环己烯烯胺无需进一步纯化即可用于与水杨醛席夫碱的环化反应。
• Understanding Solid/Solid Organic Reactions
  作者：Gadi Rothenberg、Andrew P. Downie、Colin L. Raston、Janet L. Scott

  DOI：10.1021/ja0034388

  日期：2001.9.1

  The concept of an organic reaction between two macroscopic solid particles is investigated. Thus, we study several reactions that have been recently reported to proceed "in the solid phase" and clearly show that, in most cases, grinding the two solid reactants together results in the formation of a liquid phase. This is true both for catalytic transformations (e.g., aldol condensations and oligomerization of benzylic compounds) and for noncatalytic reactions (Baeyer-Villiger oxidations, oxidative coupling of naphthols using iron chloride, condensation of amines and aldehydes to form azomethines, homo-etherification of benzylic alcohols using p-toluenesulfonic acid, and nuclear aromatic bromination with NBS). This liquefaction implies the existence of a eutectic mixture with T-fusion below ambient temperature (although both reagents have higher than ambient melting points). In cases where heating is required, it is again clear that a phase change (from solid to liquid) occurs, explaining the observed reaction kinetics. On the basis of 19 experimental examples, we discuss the possibility of solid-phase organic reactions and the implications of these findings to the reaction between two solid reagents. A general description of such reactive systems is proposed. based on a consideration of the potential for eutectic (or peritectic) formation between the constituents of the liquid phases that arise during the process of mechanical mixing of the solid reagents and products.
• Sc(OTf)3-catalyzed diastereoselective synthesis of 3,4-dihydro-4-amino-2H-1-benzopyrans
  作者：J.S Yadav、B.V.Subba Reddy、K.Chandra Sekhar、V Geetha

  DOI：10.1016/s0040-4039(01)00736-5

  日期：2001.6

  2,2-Dimethoxypropane reacts with a variety of o-hydroxybenzaldimines in the presence of a catalytic amount of scandium triflate at ambient temperature to afford a series of new compounds, 3,4-dihydro-4-amino-2-methoxy-2-methyl-2H-1-benzopyrans, in high yields, with good diastereoselectivity. BF3. OE2, is also found to mediate this transformation under mild reaction conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
• LiBF4-catalyzed formation of fused pyrano- and furanobenzopyrans
  作者：J.S Yadav、B.V.Subba Reddy、Ch Madhuri、G Sabitha、B Jagannadh、S.Kiran Kumar、A.C Kunwar

  DOI：10.1016/s0040-4039(01)01257-6

  日期：2001.9

  Lithium tetrafluoroborate efficiently catalyzes an unusual cyclization of o-hydroxybenzaldimines with 2,3-dihydrofuran and 3,4-dihydro-2H-pyran at ambient temperature to afford a class of new pyrano- and furanobenzopyran derivatives in excellent yields with high diastereo selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.