CAS: 527-61-7; 2,6-Dimethylcyclohexa-2,5-Diene-1,4-Dione

该化合物是具有五角形结构的有机化合物,其特点是在2和6个位置和1和4位置上有两个甲基组和两个碳基组的六人芳香环,在2和6个位置和2个碳基组,该化合物一般是室内温度下黄色至橙色的固体,以其强烈氧化特性而著称,在丙酮和乙醇等有机溶剂中可溶解,但在水中溶解性有限. 2,6-二甲基-1,4-苯丙酮经常用于有机合成,并在各种化学反应中用作试剂,包括涉及电传的化学反应中,其反应力可归因于五角体功能组的存在,这些组可参与再氧化反应.此外,该化合物在材料科学领域和作为其他有机化合物合成的前体方面也有应用.在处理时应采取安全防范措施,因为它可能会刺激皮肤和眼睛.

结构式图片

欧盟法规

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上下游产品

3,3’5,5’-四甲基-4,4’-联苯醌 3,3',5,5'-Tetramethyldiphenoquinone 4906-22-3

合成工艺路线路线简述

  • 合成目标产物 2,6-Dimethylbenzoquinone 主要起始原料 2,6-Dimethylphenol
  • (文献来源)合成步骤主要原料 2,6-Dimethylphenol
4-氯-2,6-二甲基苯酚置于氧气体系中,用 甲醇 作为反应溶剂,以86%的收率获得产物2,6-二甲基-2,5-环己二烯-1,4-二酮
参考文献:芳基阳离子和卡宾中间体在氯酚的光脱卤中.
标题:芳基阳离子和卡宾中间体在氯酚的光脱卤中.
摘要:通过产物研究和瞬态吸收光谱法研究了2,6-二甲基-4-氯苯酚(6)在甲醇和三氟乙醇(tfe)中的光化学反应.来自三重态6的氯化物损失产生三重态羟苯基阳离子14,其在几十纳秒内与三重态氧代环己二烯基15平衡.但是,阳离子可以被烯丙基三甲基硅烷(k(ad)= 10(8)-10(9)m(-1)s(-1))选择性捕获,从而得到a离子和烯丙基化苯酚.在纯醇中,14和15的还原机理不同,即分别通过自由基阳离子17和苯氧基16进行氢转移.通过对o-甲硅烷基化衍生物的平行研究证实了机械合理性.这项工作表明,高(但选择性)反应性苯基阳离子14的化学不仅可以与同样的高反应性卡宾15区别开来,而且还可以用于合成有用的反应,如在这种情况下与烯烃的反应.给电子取代的卤代苯的光解可能是温和反应生成某些类别的苯基阳离子的一种选择方法.
DOI:10.1002/chem.200400681

海关参考信息

专利信息


专利号:US-10266503-B1
优先权日:2016-05-24
标 题 :Sulfoxide ligand metal catalyzed oxidation of olefins
发明人:WHITE M CHRISTINA; AMMANN STEPHEN E; LIU WEI; MA RULIN
权利人:UNIV ILLINOIS
摘要:The enantioselective synthesis of isochroman motifs has been accomplished via Pd(II)-catalyzed allylic C—H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C—H oxidation reaction proceeds with the broadest scope and highest levels asymmetric induction reported to date (avg. 92% ee, 13 examples ≥90% ee). Additionally, C(sp 3 )-N fragment coupling reaction between abundant terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/sulfoxide (SOX) catalyzed intermolecular allylic C—H amination is disclosed. A range of 52 allylic amines are furnished in good yields (avg. 76%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). For the first time, a variety of singly activated aromatic and aliphatic nitrogen nucleophiles, including ones with stereochemical elements, can be used in fragment coupling stiochiometries for intermolecular C—H amination reactions.

专利号:US-9725392-B2
优先权日:2015-08-27
标 题:Efficient scalable syntheses of abscisic acid, 8′-acetylene abscisic acid and 8′-cyclopropyl abscisic acid
发明人:JHEENGUT Vishal; NELSON KEN M; ABRAMS SUZANNE R
权利人:NAT RES COUNCIL CANADA
摘要:Methods are provided for synthesis of abscisic acid and 8′ analogues thereof (including an enantiopure 8′-acetylene analogue) including methods wherein the previously reported first step of oxidation of 2,6-dimethylphenol (VI) to 2,6-dimethylbenzoquinone, mono ketal (VII) is replaced by a novel two step process comprising (i) oxidation of 2,6-dimethylphenol (VI) using potassium peroxymonosulfate with a catalytic amount of iodobenzene to produce 2,6-dimethylbenzoquinone (XVI) and (ii) ketalization of 2,6-dimethylbenzoquinone (XVI) using ethylene glycol, trimethylorthoformate with a catalytic amount of p-toluenesulfonic acid to produce 2,6-dimethylbenzoquinone, mono ketal (VII).

专利号:WO-2004009574-A1
优先权日:2002-07-22
标 题 :Synthesis of discodermolide
发明人:FLORENCE GORDON; KOCH GUIDO; LOISELEUR OLIVIER; MICKEL STUART JOHN; PATERSON IAN
权利人:NOVARTIS AG; NOVARTIS PHARMA GMBH; UNIV CAMBRIDGE TECH; FLORENCE GORDON; KOCH GUIDO; LOISELEUR OLIVIER; MICKEL STUART JOHN; PATERSON IAN
摘要:The invention relates to a process for preparing discodermolide, for preparing intermediates for the manufacture of discodermolide and discodermolide analogues and to the intermediates obtained during the process. Wherein the process proceeds via a tetraene of formula (IV).

专利号:US-2002185368-A1
优先权日:2001-06-07
标题:Synthesis of organic nanotubes and synthesis of ultrathin nanowires using same as templates

专利号:US-3920748-A
优先权日:1972-06-12
标题:Steroid total synthesis and intermediates
发明人:VALENTA ZDENEK
权利人:HOFFMANN LA ROCHE
摘要:A new steroidal synthesis process is described wherein the steroidal nucleus is provided by a Diels-Alder reaction between a 2,6-lower alkylbenzoquinone and a suitably substituted 1-vinylnaphthalene compound. Depending on the nature of the naphthalene compound it is possible to readily prepare estrones, progesterones, androstanes and cortisones having the natural configuration or if desired having the retro configuration.

专利号:US-6762331-B2
优先权日:2001-06-07
标 题:Synthesis of organic nanotubes and synthesis of ultrathin nanowires using same as templates
发明人:HONG BYUNG HEE; LEE CHI-WAN; KIM KWANG SOO
权利人:POSTECH FOUNDATION
摘要:The present invention discloses a method for synthesizing a calix[4]hydroquinone organic nanotube and a method for synthesizing an ultrathin, stable nanowire using said organic nanotube as a template.
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合成参考文献


摘要:Weibel, J.-M.; Blanc, A.; Pale, P., Science of Synthesis Knowledge Updates, (2018) 1, 33.
摘要:Wang, K.; Wang, J., Science of Synthesis, (2022) , 30.
摘要:Wang, K.; Wang, J., Science of Synthesis, (2022) , 15.
摘要:Molteni, G., Science of Synthesis: Water in Organic Synthesis, (2012) 1, 434.
摘要:Mase, N., Science of Synthesis: Water in Organic Synthesis, (2012) 1, 199.
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