4,5-dimethyl-2-hydroxybenzyl alcohol | 10496-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4,5-dimethyl-2-hydroxybenzyl alcohol
• 英文别名: 2-hydroxy-4,5-dimethyl-benzyl alcohol；6-Hydroxy-3.4-dimethyl-1-hydroxymethyl-benzol；(6-Hydroxy-3.4-dimethyl-phenyl)-methanol；2-Hydroxy-4,5-dimethyl-benzylalkohol；4.5-Dimethyl-2-hydroxymethyl-phenol；5.4¹-Dioxy-1.2.4-trimethyl-benzol；2-(Hydroxymethyl)-4,5-dimethylphenol
• CAS: 10496-92-1
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: HCEVEUBXZBBHOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dimethyl-2-hydroxybenzyl alcohol 在 1% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到2,4,5-三甲酚
  参考文献：
  名称：

  芳烃到二喹烷：四甲基双环 [3.3.0] 辛烷内酯骨架的快速合成

  摘要：

  描述了从简单的芳族前体制备 7-氧-1,4,5,8-四甲基双环 (3.3.0) 辛烷-3-羧酸甲酯的快速途径。将 2-羟基-甲基-3,4,6-三甲基苯酚氧化脱芳构化为螺环环氧环己-2,4-二烯酮、其环加成和三线态敏化 1,2-酰基转移和立体化学转化是我们方法的关键特征.

  DOI：

  10.1055/s-0028-1087275
• 作为产物：
  描述：

  3,4-二甲基苯酚 、 聚合甲醛 在 sodium metaborate tetrahydrate 作用下， 以 水 为溶剂， 反应 10.0h， 以95%的产率得到4,5-dimethyl-2-hydroxybenzyl alcohol
  参考文献：
  名称：

  Water-promoted ortho-selective monohydroxymethylation of phenols in the NaBO₂ system

  摘要：

  在NaBO2体系中，水促进了酚的ortho-选择性单羟甲基化反应，产生了优良产率的水杨醇。

  DOI：

  10.1039/c4ob00228h

文献信息

• Ethers and thioethers of kojic acid and preparation thereof
  申请人：RHONE POULENC SA

  公开号：US02865930A1

  公开（公告）日：1958-12-23

  The invention comprises compounds of the formula <;FORM:0781413/IV (a)/1>; where R is alkyl, X is O or NH, Y is O or S, and Ar is aryl, which may have one or more alkyl, alkoxy, hydroxyalkyl, nitro or halogen substituents; the alkyl and alkoxy groups have not more than 4 carbon atoms. The compounds are prepared (1) by the action of H-Y-Ar on the appropriate pyrones or pyridones having a -CH2Z substituent where Z is a reactive ester group such as halide, sulphuric or sulphonic ester, preferably in a solvent at 50-100 DEG C. in the presence of a basic condensing agent, or (2) by the alkylation of the corresponding 5-hydroxy compounds. In addition the pyridones may be made from the pyrones by heating with ammonia. Examples show the preparation by method (1) of 2-aryloxymethyl-5 - methoxy - 4 - pyrones where aryl group is phenyl, b -naphthyl, and the following substituted phenyl groups:-chloro (3 isomers), 2:4-dichloro, 2:4:6-trichloro, pentachloro, methyl (3 isomers), dimethyl (6 isomers), 2:4:6-trimethyl, 2-methyl-4- and -6-chloro, 3-methyl-4-chloro, 4-methyl-2-chloro, 2-methyl-4:6-dichloro, 4 - methyl - 2:6 - dichloro, 2:4 - dimethyl-6-chloro, 3:5-dimethyl-4-chloro, 4-isopropyl, 4-cyclohexyl, 2- and 4-nitro, 2-methylol, 2:4 - dichloro - 6 - methylol, 2 - chloro - 4:6 - dimethylol, 4 - chloro - 2:6 - dimethylol, 4 - methyl - 2 - methylol, 4 - methyl - 2:6 - dimethylol, 2:5 - dimethyl - 4 - methylol, 3:4 - dimethyl - 6 - methylol, 3 - methoxy, and 2 - methoxy-4-, -5- and -6-methyl; also 2-(21-methylolphenoxymethyl) - 5 - ethoxy - 4 - pyrone and 2-(41-chlorophenylthiomethyl) - 5 - methoxy-4-pyrone. I further examples 2-(41 chlorophenoxymethyl) - 5 - methoxy - 4 - pyridone (hydrochloride described) and 2-(21-methyl - 61 - chlorophenoxymethyl) - 5 - methoxy-4-pyridone are made from the corresponding pyrones and ammonia. It is also stated that Ar may also be ethylphenyl, ethoxyphenyl or hydroxy-ethyl-phenyl.ALSO:Compositions for use as plant growth regulants contain as active ingredient a compound of the formula: <;FORM:0781413/I/1>; where R is alkyl, X is O or NH, Y is O or S and Ar is aryl which may have one or more alkyl, alkoxy, hydroxyalkyl, nitro or halogen substituents; the alkyl and alkoxy groups have not more than 4 carbon atoms. The compositions may be in the form of powders, sprays, aerosols, emulsions or solutions in organic or aqueous organic solvents. There may also be present wetting agents, synergists and other plant growth regulants. In an example 2-(21 : 41-dichlorophenoxymethyl)-5-methoxy-4-pyrone is dissolved in dimethylformamide and diluted with water to give a solution which enhances root formation when plant stems are soaked with it. Many other suitable compounds are mentioned.ALSO:Compositions for use as systemic fungicides or herbicides contain as essential ingredient a compound of the formula <;FORM:0781413/VI/1>; where R is alkyl, X is O or NH, Y is O or S and Ar is aryl which may have one or more alkyl, alkoxy, hydroxyalkyl, nitro or halogen substituents; the alkyl and alkoxy groups have not more than 4 carbon atoms. The compositions may be in the form of powders, sprays, aerosols, emulsions or solutions in organic or aqueous organic solvents. There may also be present wetting agents, synergists, and other plant-growth regulants or fungicides. In examples, fungicides are made of (1) 2-(21-methyl - 41 - chlorophenoxymethyl) - 5 - methoxy-4-pyrone dispersed in water with the aid of a wetting agent; and (2) 2-(31:51-dimethylphenoxy - methyl) - 5 - methoxy - 4 - pyrone and talc similarly dispersed; herbicides are made from (3) 2-(2-(21:41-dichlorophenoxymethyl) - 5 - methoxy - 4 - pyrone; and (4) 2-(41 - chlorophenoxymethyl) - 5 - methoxy - 4-pyrone, in each case dissolved in toluene and acetone and dispersed in water with the aid of a wetting agent. Many other suitable compounds are mentioned.

  该发明包括以下公式的化合物：其中R为烷基，X为O或NH，Y为O或S，Ar为芳基，可能具有一个或多个烷基、烷氧基、羟基烷基、硝基或卤素取代基；烷基和烷氧基基团的碳原子数不超过4。这些化合物通过以下方法制备：（1）在适当的吡喃酮或吡啶酮上作用H-Y-Ar，其中吡喃酮或吡啶酮具有一个-CH2Z取代基，其中Z是反应性酯基，如卤化物、硫酸酯或磺酸酯，最好在50-100摄氏度的溶剂中，在碱性缩合剂的存在下进行，或者（2）通过对应的5-羟基化合物的烷基化制备。此外，吡啶酮可以通过与氨加热制备。示例表明，通过方法（1）制备了2-芳氧基甲基-5-甲氧基-4-吡喃，其中芳基为苯基、β-萘基，以及以下取代苯基：氯（3个异构体）、2,4-二氯、2,4,6-三氯、五氯、甲基（3个异构体）、二甲基（6个异构体）、2,4,6-三甲基、2-甲基-4-和-6-氯、3-甲基-4-氯、4-甲基-2-氯、2-甲基-4,6-二氯、4-甲基-2,6-二氯、2,4-二甲基-6-氯、3,5-二甲基-4-氯、4-异丙基、4-环己基、2-和4-硝基、2-甲基醇、2,4-二氯-6-甲基醇、2-氯-4,6-二甲基醇、4-氯-2,6-二甲基醇、4-甲基-2-甲基醇、4-甲基-2,6-二甲基醇、2,5-二甲基-4-甲基醇、3,4-二甲基-6-甲基醇、3-甲氧基、2-甲氧基-4-, -5-和-6-甲基；还有2-(21-甲基醇苯氧基甲基)-5-乙氧基-4-吡喃和2-(41-氯苯硫醚基甲基)-5-甲氧基-4-吡喃。另外还有一些其他化合物的例子。
• Iridium-Catalyzed Asymmetric Hydrogenation of 2<i>H</i>-Chromenes: A Highly Enantioselective Approach to Isoflavan Derivatives
  作者：Jingzhao Xia、Yu Nie、Guoqiang Yang、Yangang Liu、Wanbin Zhang

  DOI：10.1021/acs.orglett.7b02341

  日期：2017.9.15

  A highly efficient (aS)-Ir/In-BiphPHOX-catalyzed asymmetric hydrogenation of substituted 2H-chromenes and substituted benzo[e][1,2]oxathiine 2,2-dioxides is described. A series of 2H-chromenes and benzo[e][1,2]oxathiine 2,2-dioxides were hydrogenated to give the target products in high yields (92–99%) with excellent enantioselectivities (up to 99.7% ee) using our catalytic system. This reaction provides

  描述了一种高效的（S）-Ir / In-BiphPHOX催化的取代2 H-色烯和取代苯并[ e ] [1,2]草嘌呤2,2-二氧化物的不对称氢化反应。一系列2 H-色烯和苯并[ e ] [1,2]草嘌呤2,2-二氧化物被氢化，以高收率（92-99％）得到具有优异对映选择性（高达99.7％ee）的目标产物我们的催化系统。该反应为构建手性苯并六元含氧化合物提供了直接而有效的方法。
• Highly Functionalized Tricyclic Oxazinanones via Pairwise Oxidative Dearomatization and <i>N</i>-Hydroxycarbamate Dehydrogenation: Molecular Diversity Inspired by Tetrodotoxin
  作者：Steffen N. Good、Robert J. Sharpe、Jeffrey S. Johnson

  DOI：10.1021/jacs.7b07745

  日期：2017.9.13

  Benzenoids in principle represent attractive and abundant starting materials for the preparation of substituted cyclohexanes; however, the synthetic tools available for overcoming the considerable aromatic energies inherent to these building blocks limit the available product types. In this paper, we demonstrate access to heretofore unknown heterotricyclic structures by leveraging oxidative dearomatization

  苯类原则上代表了用于制备取代环己烷的有吸引力且丰富的原料；然而，可用于克服这些构件固有的大量芳烃能量的合成工具限制了可用的产品类型。在本文中，我们通过使用普通氧化剂利用 2-羟甲基苯酚的氧化脱芳构化和同时进行的 N-羟基氨基甲酸酯脱氢，证明了获得迄今为止未知的杂三环结构。成对生成的、相互反应的物质然后参与第二阶段的酰基亚硝基 Diels-Alder 环加成反应。衍生的 [2.2.2]-oxazabicycles 具有四个正交官能团和三个立体中心，其反应化学显示下游产品具有相当大的多样性。
• Selective Reactions between Phenols and Formaldehyde. A Superior Synthesis of Salicyl Alcohols
  作者：Giovanni Casiraghi、Giuseppe Casnati、Giuseppe Puglia、Giovanni Sartori

  DOI：10.1055/s-1980-28942

  日期：——
• Quinone dehydrogenation. Oxidation of benzylic alcohols with 2,3-dichloro-5,6-dicyanobenzoquinone
  作者：Hans Dieter Becker、Anders Bjoerk、Erich Adler

  DOI：10.1021/jo01297a010

  日期：1980.4

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