3,3’5,5’-四甲基-4,4’-联苯醌 | 4906-22-3

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3,3’5,5’-四甲基-4,4’-联苯醌
• 中文别名: 4-(3,5-二甲基-4-氧代-2,5-环己二烯-1-基)-2,6-二甲基-2,5-环己二烯-1-酮；3,3'5,5'-四甲基-4,4'-联苯醌；3,5,3,5-四甲基-4,4-二苯醌；3,3"5,5"-四甲基-4,4"-联苯醌
• 英文名称: 3,3',5,5'-tetramethyldiphenoquinone
• 英文别名: 3,3',5,5'-tetramethyl-4,4'-diphenoquinone；3,5,3',5'-tetramethyl-4,4'-diphenoquinone；4-(3,5-dimethyl-4-oxo-2,5-cyclohexadienylidene)-2,6-dimethyl-2,5-cyclohexadienone；3,3',5,5'-tetramethyl-[1,1'-bi(cyclohexylidene)]-2,2',5,5'-tetraene-4,4'-dione；3,3′,5,5′-tetramethyl-4,4′-diphenoquinone；4-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-2,6-dimethylcyclohexa-2,5-dien-1-one
• CAS: 4906-22-3
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: QDRFIDSUGRGGAY-UHFFFAOYSA-N

物化性质

• 熔点：
  205-207 ºC
• 沸点：
  375.1±42.0 °C(Predicted)
• 密度：
  1.123

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  3,3’5,5’-四甲基-4,4’-联苯醌 在 高氯酸 、 lead dioxide 作用下， 以 丙酮 为溶剂， 反应 0.25h， 以29%的产率得到2,6-二甲基-2,5-环己二烯-1,4-二酮
  参考文献：
  名称：

  Oxidation of 4,4′-diphenoquinones giving p-benzoquinones

  摘要：

  4,4'-Diphenoquinone 1a can be oxygenated to give p-benzoquinone 2a when treated with PbO2 in a solvent containing an aqueous acid. The conversion of la is facilitated when the acid is strong and the solvent is of low basicity. The concentration of H2O in the medium also has a profound effect on the rate of conversion of 1a. These facts may indicate that protonation of la is the first step in the conversion into 2a. 4,4'-Diphenoquinones 1b and 1c can be analogously converted into p-benzoquinones 2a and 2b, respectively. Benzoquinones 2 can thus be the ultimate products of both oxygenation and dehydrogenative dimerization of phenols 3. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02139-5
• 作为产物：
  描述：

  2,6-二甲基苯酚 在 Ph₃BiCO₃ 、 亚硝基苯 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以60%的产率得到3,3’5,5’-四甲基-4,4’-联苯醌
  参考文献：
  名称：

  五价有机铋试剂的化学作用：第十一部分。与位阻酚的反应

  摘要：

  在碱性条件下，研究了Bi V试剂对在2和6处具有叔丁基的受阻酚的反应性。在4-位发生意外的苯基化，并且在某些情况下，观察到叔丁基被苯基取代。已经讨论了这些反应的机理。

  DOI：

  10.1016/s0040-4020(01)86150-0

文献信息

• Oxidation of Phenols and Hydroquinones by Dioxygen Catalyzed by Mixed Addenda Heteropolyoxometalate on Active Carbon (NPV₆Mo₆/C)
  作者：Shinya Fujibayashi、Kouichi Nakayama、Yutaka Nishiyama、Yasutaka Ishii

  DOI：10.1246/cl.1994.1345

  日期：1994.7

  Vanadomolybdophosphate supported on active carbon, NPV6Mo6/C, catalyzed the oxidation and coupling reaction of 2,3,6-trimethylphenol by dioxygen to give trimethyl-p-benzoquinone and 4,4′-dihydroxy-2,2′,3,3′,5,5′-hexamethylbiphenyl, respectively, depending on the solvent used. Hydroquinones and benzyl alcohol were selectively dehydrogenated by the present system, giving the corresponding p-benzoquinones and benzaldehyde, respectively, in good yields.

  负载于活性炭上的钒钼磷酸盐NPV6Mo6/C催化二甲基苯酚与氧气氧化偶联反应，根据所用溶剂的不同，分别得到三甲基对苯醌和4,4′-二羟基-2,2′,3,3′,5,5′-六甲基联苯。该体系可选择性地脱氢生成相应的对苯醌和苯甲醛，且产率良好。
• Oxidation by Cobalt(III) Acetate. Part 13. Oxidation of Substituted Phenols with Cobalt(III) Acetate in Acetic Acid
  作者：Masao Hirano、Tadamichi Ishii、Takashi Morimoto

  DOI：10.1246/bcsj.64.1434

  日期：1991.4

  The oxidation of 2,6-di- and 2,4,6-tri-substituted phenols with cobalt(III) acetate has been investigated in acetic acid under an inert atmosphere; the former gave the corresponding diphenoquinones in excellent yields, and the latter yielded side-chain or nuclear acetoxylated products in moderate to good yields.

  2,6-二-和2,4,6-三-取代苯酚与乙酸钴（III）在惰性气氛下的乙酸中的氧化研究；前者以极好的收率产生相应的二苯醌，而后者以中等至良好的收率产生侧链或核乙酰氧基化产物。
• Selective, Catalytic, and Metal-Free Coupling of Electron-Rich Phenols and Anilides Using Molecular Oxygen as Terminal Oxidant
  作者：Luis Bering、Melina Vogt、Felix M. Paulussen、Andrey P. Antonchick

  DOI：10.1021/acs.orglett.8b01631

  日期：2018.7.6

  Selective oxidative homo- and cross-coupling of electron-rich phenols and anilides was developed using nitrosonium tetrafluoroborate as a catalyst. Oxidative coupling of phenols revealed unusual selectivities, which translated into the unprecedented synthesis of inverse Pummerer-type ketones. Mechanistic studies suggest that oxidative coupling of phenols and anilides shares a common pathway via homolytical

  使用四氟硼酸氮鎓作为催化剂，开发了富电子的苯酚和苯甲酸酯的选择性氧化均相和交叉偶联。酚类的氧化偶联显示出不同寻常的选择性，这转化为反Pummerer型酮的空前合成。机理研究表明，酚和苯甲酸酯的氧化偶合通过均质杂原子-氢键裂解具有共同的途径。硝盐催化被应用到由杂原子为中心的自由基的产生引发的交叉脱氢偶联。
• Solvent-controlled selective synthesis of biphenols and quinones via oxidative coupling of phenols
  作者：Nagnath Yadav More、Masilamani Jeganmohan

  DOI：10.1039/c7cc04829g

  日期：——

  A regioselective synthesis of unsymmetrical and symmetrical biphenols and binaphthols via oxidative coupling of phenols or naphthols in the presence of K2S2O8 in CF3COOH at ambient conditions is described. Interestingly, 1:1 ratio of H2O and CH3CN solvent mixtures at 80 °C instead of CF3COOH provided substituted unsymmetrical quinones. A gram scale synthesis of biphenols and binaphthols was demonstrated

  描述了在环境条件下在CF 3 COOH中在K 2 S 2 O 8存在下通过酚或萘酚的氧化偶联的不对称和对称的双酚和联萘酚的区域选择性合成。有趣的是，在80°C的H2O和CH3CN溶剂混合物以1：1的比例代替CF3COOH提供了取代的不对称醌。证明了双酚和联萘酚的克级合成。
• PHOSPHORUS-CONTAINING COMPOUND AND METHOD FOR PREPARING THE SAME
  申请人：Chen Gai-Chi

  公开号：US20100105939A1

  公开（公告）日：2010-04-29

  The present invention provides a phosphorus-containing compound of formula (I): wherein R 1 , R 2 , R 3 and R 4 are the same or different; and R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of hydrogen, halogen, C 1-8 alkyl, haloalkyl, and alkoxy. The phosphorus-containing compound is prepared by bonding a bisphenol group to a phosphorus atom to prevent the phosphorus-containing heterocyclic molecule from exhibiting steric hindrance on hydroxyl functional groups, thereby increasing reactivity in the subsequent reactions.

  本发明提供了一种含磷化合物，其化学式为（I）：其中R1、R2、R3和R4可以相同也可以不同；R1、R2、R3和R4独立地选自氢、卤素、C1-8烷基、卤代烷基和烷氧基等基团。所述含磷化合物通过将双酚基团与磷原子键合以防止含磷杂环分子在羟基官能团上表现出位阻，从而提高在随后的反应中的反应性。

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