2,6-dimethoxy-4-(methoxymethyl)phenol | 60824-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,6-dimethoxy-4-(methoxymethyl)phenol
• CAS: 60824-64-8
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: LFAJIBQRSUUNSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dimethoxy-4-(methoxymethyl)phenol 在 氨 、 lithium 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 18.0h， 生成 3,3',5,5'-四甲氧基-联苄基
  参考文献：
  名称：

  Deoxygenation of highly hindered phenols

  摘要：

  DOI：

  10.1021/jo00290a033
• 作为产物：
  描述：

  [2,6-dimethoxy-4-(methoxymethyl)phenyl]boronic acid 在 双氧水 作用下， 以 水 为溶剂， 以96%的产率得到2,6-dimethoxy-4-(methoxymethyl)phenol
  参考文献：
  名称：

  Design, synthesis and structure–activity relationships of 5-alkylaminolquinolines as a novel series of CRF1 receptor antagonists

  摘要：

  A series of 5-alkylaminolquinolines was designed and synthesized as potential novel CRF1 receptor antagonists. The structure-activity relationships (SARs) of the substituents on each position (R-2, R-3, R-5 and R-5') were investigated. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.066

文献信息

• Cu(OAc)₂-catalyzed remote benzylic C(sp³)–H oxyfunctionalization for CO formation directed by the hindered para-hydroxyl group with ambient air as the terminal oxidant under ligand- and additive-free conditions
  作者：Jian-An Jiang、Cheng Chen、Jian-Gang Huang、Hong-Wei Liu、Song Cao、Ya-Fei Ji

  DOI：10.1039/c3gc41946k

  日期：——

  A hindered para-hydroxyl group-directed remote benzylic C(sp3)–H oxyfunctionalization has been developed for the straightforward transformation of 2,6-disubstituted 4-cresols, 4-alkylphenols, 4-hydroxybenzyl alcohols and 4-hydroxybenzyl alkyl ethers into various aromatic carbonyl compounds. The ligand- and additive-free Cu(OAc)2-catalyzed atmospheric oxidation mediated by ethylene glycol unlocks a

  已经开发了一种受阻的对羟基定向的远程苄基C（sp 3）–H氧官能团，用于将2,6-二取代的4-甲酚，4-烷基苯酚，4-羟基苄醇和4-羟基苄基烷基醚直接转化为各种芳族羰基化合物。由乙二醇介导的无配体和无添加剂的Cu（OAc）2催化的大气氧化作用，可以使伯苄基和仲苄基官能化，形成简便，原子经济且对环境无害的C O形成。由于4-羟基苯甲醛和4-羟基苯酮的药物重要性，因此该方法对于基础研究和实际应用均具有重要价值。
• Selective Oxidation of Phenols to Hydroxybenzaldehydes and Benzoquinones with Dioxygen Catalyzed by Polymer-Supported Copper
  作者：Ken Takaki、Yohei Shimasaki、Tetsuya Shishido、Katsuomi Takehira

  DOI：10.1246/bcsj.75.311

  日期：2002.2

  Oxidation of 2,6-disubstituted 4-methylphenols with dioxygen by using a CuCl2-poly(4-methyl-4′-vinyl-2,2′-bipyridine) catalyst gave the corresponding 4-hydroxybenzaldehydes in high yields. The activity of the catalyst and the selectivity of the products significantly depended on the reaction conditions and the composition of the catalyst. When the molar ratio of the bipyridine unit of the polymer ligand to Cu was unity, i.e., N/Cu = 2, the best results were obtained. Moreover, the reaction is likely to be promoted by coordination of the products to the catalyst. Similarly, 2,3,6-trimethylphenol and related compounds were converted to p-benzoquinones selectively with a CuCl2-poly(4-vinylpyridine) catalyst. These polymer-supported catalysts were readily recovered and are reusable without noticeable decrease of their activity.

  用CuCl2-聚(4-甲基-4'-乙烯基-2,2'-吡啶)催化剂与氧气氧化2,6-二取代4-甲基苯酚，得到了相应的4-羟基苯甲醛，高收率。催化剂的活性和产物的选择性显著依赖于反应条件和催化剂的组成。当聚合物配体的双吡啶单元与铜的摩尔比为1，即N/Cu = 2时，获得最佳结果。此外，反应可能通过产物与催化剂的配位得到促进。同样，2,3,6-三甲基苯酚及相关化合物在CuCl2-聚(4-乙烯基吡啶)催化剂的作用下选择性转化为对苯醌。这些聚合物支撑的催化剂容易回收，且在不显著降低活性的情况下可重复使用。
• Nickel-catalyzed intelligent reductive transformation of the aldehyde group using hydrogen
  作者：Xinli Tong、Pengfei Guo、Shengyun Liao、Song Xue、Haigang Zhang

  DOI：10.1039/c9gc01116a

  日期：——

  The selective transformation of the aldehyde group (–CHO) in multifunctional oxygenates is a key challenge in the development of sustainable biomass feedstock. Herein, a smart Ni-MFC catalyst was developed from a 2D Ni-based metal–organic framework (MOF), which efficiently promoted the transformation of –CHO in the presence of H2 to a methyl group (–CH3) via the reductive etherification and hydrogenolysis

  多功能含氧化合物中醛基（–CHO）的选择性转化是可持续生物质原料开发中的关键挑战。在此，从2D Ni基金属-有机骨架（MOF）开发了一种智能Ni-MFC催化剂，该催化剂可有效地促进H 2存在下–CHO通过还原性还原为甲基（–CH 3）醚在甲醇中的醚化和氢解。此外，可以控制催化过程以定向产生甲醚（–CH 2OR）使用还原醚化协议。为了催化还原香草醛，Ni-MFC-700催化剂保证了香草醛的完全转化和所需2-甲氧基-4-甲基苯酚（MMP）的96.5％产率，而Ni-MFC-500催化剂提供了约82.7％的纯度。甲醇溶剂中4-（甲氧基甲基）-2-甲氧基苯酚的收率。这是一种新颖和有前途的方法，用于对多功能含氧化合物和生物质衍生的平台化合物进行增值。
• On the metalation of phenolic compounds: Ready access to highly substituted phenols.
  作者：Antonio Costa、José M. Saá

  DOI：10.1016/s0040-4039(00)96778-9

  日期：1987.1

  studied. Those substrates possesing an electron-withdrawing group in a 1,3 relationship with the coordinating (-CH2OMe) group underwent regioselective metalation by the action of n-BuLi/THF. Highly substituted phenols can thus be readly prepared.

  已经研究了几种对羟基苄基甲基醚的直接金属化。那些具有与配位基团（-CH 2 OMe）成1,3关系的吸电子基团的底物在n-BuLi / THF的作用下进行了区域选择性金属化。因此可以容易地制备高度取代的酚。
• Catalyst- and Oxidizing Reagent-Free Electrochemical Benzylic C(sp³)–H Oxidation of Phenol Derivatives
  作者：Zhong-Wei Hou、Ming-Ming Zhang、Wen-Chao Yang、Lei Wang

  DOI：10.1021/acs.joc.2c00455

  日期：2022.6.17

  A site-selective electrochemical approach for the benzylic C(sp3)–H oxidation reaction of phenol derivatives along with hydrogen evolution has been developed. The protocol proceeds in an easily available undivided cell at room temperature under catalyst- and oxidizing reagent-free conditions. The corresponding aryl aldehydes and ketones are obtained in satisfactory yields, and the gram-scale synthesis

  已经开发了一种用于苯酚衍生物的苄基 C(sp 3 )-H 氧化反应以及析氢的位点选择性电化学方法。该协议在无催化剂和无氧化剂条件下在室温下在一个容易获得的未分裂电池中进行。相应的芳基醛和酮均以满意的收率得到，且易于进行克级合成。