2,6-二乙基-1,4-苯醌 | 50348-20-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,6-二乙基-1,4-苯醌
• 英文名称: 2,6-diethyl-1,4-benzoquinone
• 英文别名: 2,6-diethyl-p-benzoquinone；3,5-diethyl-p-benzoquinone；2,6-diethyl-[1,4]benzoquinone；2,6-Diaethyl-[1,4]benzochinon；1.3-Diaethyl-cyclohexadien-(3.6)-dion-(2.5)；2,5-Cyclohexadiene-1,4-dione, 2,6-diethyl-；2,6-diethylcyclohexa-2,5-diene-1,4-dione
• CAS: 50348-20-4
• 化学式: C₁₀H₁₂O₂
• mdl: MFCD00830720
• 分子量: 164.204
• InChiKey: MLSVZZQOVPGKRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  2,6-二乙基-1,4-苯醌 在 sodium dithionite 、 水 作用下， 生成 2,6-diethylhydroquinone
  参考文献：
  名称：

  d，l -5,7-二炔基生育酚，e-同源物，α-生育酚

  摘要：

  DOI：

  10.1002/hlca.19410240143
• 作为产物：
  描述：

  2,6-二乙基苯胺 在 cerium(IV) chlorate 、 对氨基苯酚 作用下， 以 高氯酸 为溶剂， 以44%的产率得到2,6-二乙基-1,4-苯醌
  参考文献：
  名称：

  Oxidative cross-coupling of some 2,6- and N,N-disubstituted aniline derivatives with 4-aminophenol mediated by cerium(IV) ions in aqueous perchloric acid

  摘要：

  The mechanism of the oxidation of mixtures of 2,6-dimethylaniline (1), N,N-dimethylaniline (2), 2,6-diethylaniline (3), N,N-diethylaniline (4), N-methylaniline (5), 2,6-difluoroaniline (6), and 2,3,5,6-tetrafluoroaniline (7) with 4-aminophenol (8) by cerium(IV) ions in aqueous perchloric acid has been investigated. The indoaniline salts [O=C6H4=N-C6H2(R-1)(2)NH(R-2)(2)]+ClO4- (R-1 = H, R-2 = CH3, C2H5 or vice versa) are formed as intermediates in the cross-coupling reaction; they undergo oxidation to imino-4-benzoquinone (9) and its corresponding derivatives by cerium(IV) ions in high yields. The mechanism of this process is discussed.

  DOI：

  10.1007/bf00807085

文献信息

• The Reaction of Nitrile Oxide-Quinone Cycloadducts. III. Reinvestigation of the Base-Induced Isomerization of the 1 : 1 -C=C-Adducts of Aromatic Nitrile Oxides with 2,5- and 2,6-Dialkyl-Substituted<i>p</i>-Benzoquinones
  作者：Takashi Mukawa、Yukihiko Inoue、Shinsaku Shiraishi

  DOI：10.1246/bcsj.72.2549

  日期：1999.11

  The structure of the product obtained by the base-induced isomerization of the 1,3-dipolar cycloadduct of 2,5-di-t-butyl-p-benzoquinone with 2,6-dichlorobenzonitrile oxide was determined by X-ray analysis. The t-butyl group at the bridgehead position of the 1,3-dipolar cycloadduct migrated to the neighboring carbonyl carbon atom. This base-induced rearrangement took place with a bulky group, i. e., Et, i-Pr, t-Bu, and Bn at the bridgehead position of nitrile oxide-quinone cycloadducts in an alcoholic media. The driving force of this reaction is considered to be due to stabilization by aromatization from isoxazoline derivatives to isoxazole-fused p-quinol derivatives.

  通过X射线分析确定了2,5-二-叔丁基-p-苯醌与2,6-二氯苯腈氧化物的1,3-极性环加成物在碱引发异构化后的产物结构。1,3-极性环加成物中桥头位置的叔丁基团迁移至相邻的羰基碳原子。这种碱引发的重排在含有庞大取代基（即乙基、异丙基、叔丁基和苄基）的腈氧化物-醌环加成物在醇介质中发生。这一反应的驱动力被认为是由于从异噁唑啉衍生物到异噁唑融合p-喹啉衍生物的芳构化稳定作用。
• Exploiting Alkylquinone Tautomerization: Amine Benzylation
  作者：Luis M. Mori-Quiroz、Michael D. Clift

  DOI：10.1021/acs.orglett.6b01629

  日期：2016.7.15

  A general protocol for the synthesis of benzylic amines via side-chain amination of alkylquinones is reported. The reactions are initiated by the tautomerization of an alkylquinone to the corresponding quinone methide, which is subsequently trapped in situ by an amine nucleophile. This process is promoted by tertiary amines in protic solvents under mild conditions and is compatible with many functional

  据报道，通过烷基醌的侧链胺化合成苄基胺的一般方案。通过将烷基醌互变异构化为相应的醌甲基化物来引发反应，随后将其甲基化地被胺亲核试剂捕获。在温和条件下，质子溶剂中的叔胺促进了该过程，并且与许多官能团相容。1,2-和1,4-苯醌，以及萘醌，使用各种各样的伯胺和仲胺/苯胺参与该反应。还探讨了这种转化的综合效用。
• Aumueller, Alexander; Huenig, Siegfried, Liebigs Annalen der Chemie, 1986, # 1, p. 142 - 164
  作者：Aumueller, Alexander、Huenig, Siegfried

  DOI：——

  日期：——
• The Effect of Alkyl Groups on 4-Nitro- and 4-Nitroso-phenols
  作者：WYMAN R. VAUGHAN、G. KIRKWOOD FINCH

  DOI：10.1021/jo01117a001

  日期：1956.11
• Henderson; Boyd, Journal of the Chemical Society, 1910, vol. 97, p. 1661
  作者：Henderson、Boyd

  DOI：——

  日期：——