2,5-di-tert-butyl-6-hydroxy-1,4-benzoquinone | 23803-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-di-tert-butyl-6-hydroxy-1,4-benzoquinone
• 英文别名: 2-hydroxy-3,6-di-tert-butyl-p-benzoquinone；3-Hydroxy-2,5-di-tert-butyl-benzochinon-(1,4)；3,6-di(tert-butyl)2-hydroxy-p-benzoquinone；2,5-Di-tert-butyl-3-hydroxycyclohexa-2,5-diene-1,4-dione；2,5-ditert-butyl-3-hydroxycyclohexa-2,5-diene-1,4-dione
• CAS: 23803-85-2
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: OIBNNHWXRCJHCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-di-tert-butyl-6-hydroxy-1,4-benzoquinone 在 di(tert.-butoxy)-tert.-butylperoxyaluminum 作用下， 以 苯 为溶剂， 生成 3,6-di-tert-butyl-2,3-epoxy-5-hydroxy-p-benzoquinone
  参考文献：
  名称：

  Low-temperature oxidation of 3,6-di-tert-butyl-o-benzoquinone and 3,6-di-tert-butylpyrocatechol with tert-butyl hydroperoxide in the presence of aluminum, titanium, and zirconium tert-butylates

  摘要：

  Systems consisting of metal (Al, Ti, Zr) tert-butylate and tert-butyl hydroperoxide oxidize 3,6-ditert-butyl-o-benzoquinone under mild conditions (room temperature, benzene). With (t-BUO)(3)Al and (t-BUO)(4)Zr, the major reaction products are 5-hydroxy-3,6-di-tert-butyl-2,3-epoxy-p-benzoquinone, and with (t-BUO)(4)Ti, 2-hydroxy-3,6-di-tert-butyl-p-benzoquinone. Under the conditions of this reaction, 3,6-di-tert-butylpyrocatechol initially transforms into 3,6-di-tert-butyl-o-benzoquinone. The reactions involve metal-containing peroxides.

  DOI：

  10.1134/s1070363206080202
• 作为产物：
  描述：

  3,6-di-tert-butylbenzene-1,2-diol 在 叔丁基过氧化氢 、 di-tert-butyl peroxyoxalate 、 di(tert.-butoxy)-tert.-butylperoxyaluminum 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 2,5-di-tert-butyl-6-hydroxy-1,4-benzoquinone
  参考文献：
  名称：

  Reactions of hydroxyl-containing compounds with tert-butyl hydroperoxide in the presence of chromium tetra-tert-butoxide

  摘要：

  Primary and secondary aliphatic, alkylaromatic, cyclic, and organoelement alcohols are efficiently oxidized by tert-butyl hydroperoxide in the presence of both equimolar and catalytic quantities of chromium tetra-tert-butoxide (D(6)De(6), 20A degrees D). alpha-Diols containing tertiary hydroxyl groups interact with this system via oxidative splitting of the carbon scaffold. The oxidation includes the stages of formation and decomposition of chromium-containing peroxy compounds. Further transformations of the carbonyl compounds depend on the structure of radicals in the molecules.

  DOI：

  10.1134/s1070363215110080
• 作为试剂：
  描述：

  在 2,5-di-tert-butyl-6-hydroxy-1,4-benzoquinone 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Tin(IV) complexes based on 2-hydroxy-3,6-di-tert-butyl-para-benzoquinone: Syntheses, structures, and electrochemical behavior in solution

  摘要：

  A series of new tin(IV) complexes based on 2-hydroxy-3,6-di-tert-butyl-para-benzoquinone (LH) of the general formula L2SnR2 (R = Me (I), Et (II), Bu-n (III), Ph (IV)) and LSnMe3 (V) were synthesized. The obtained compounds were characterized by IR and H-1, C-13 and Sn-119 NMR spectroscopy and elemental analysis. The X-ray diffraction analysis was carried out for complexes L2Sn(Bu-n)(2) (III) and LSnMe3 (V). The low-frequency region of the IR spectra, which has not earlier been studied in detail, was interpreted for compounds I-V and previously described complex LSnPh3 (VI). The electrochemical properties of LH and related tin complexes I-VI were studied. The nature of the hydrocarbon groups at the metal atom affects the stability of the intermediates formed in the electrochemical reactions.

  DOI：

  10.1134/s1070328414040083

文献信息

• Photoinduced reactions—LVII
  作者：T. Matsuura、H. Matsushima、S. Kato、I. Saito

  DOI：10.1016/s0040-4020(01)88931-6

  日期：1972.1

  Dye-sensitized and nonsensitized photooxygenation of 3,5-di-t-butylpyrocatechol (1), 2,5-di-t-butylhydroquinone (14), their monomethyl ethers 4 and 20, and dimethyl ethers 5 and 21 has been investigated. In methanol, 1 and 4 undergo oxidative ring cleavage to give a lactonic acid 2 and/or its methyl ester 3. This represents a model for the enzymatic cleavage of phenolic rings. Under similar conditions

  已经研究了3,5-二叔丁基邻苯二酚（1），2,5-二叔丁基对苯二酚（14），它们的单甲醚4和20以及二甲醚5和21的染料敏化和非敏化光氧化作用。在甲醇中，1和4进行氧化环裂解，得到内酯酸2和/或其甲酯3。这代表了酚环的酶促裂解的模型。在相似的条件下14和20得到2,5-二叔丁基苯醌15以及进一步的转型产品。提出了涉及初始形成相应的苯氧基的机理。在这些条件下，二甲醚5和20不反应。描述了其他相关的反应。
• Reactions of isomeric 3,6- and 3,5-di-tert-butyl-ortho-benzoquinones with NH3
  作者：V. B. Vol'eva、T. I. Prokofeva、A. I. Prokofev、I. S. Belostotskaya、N. L. Komissarova、V. V. Ershov

  DOI：10.1007/bf01151298

  日期：1995.9

  (NH4)2CO3 in a solid phase has been studied. Redox processes with participation of a nucleophile of the medium take place for1, while2 reacts with NH3 at the carbonyl group with transformation of the quinone imide. The mechanism of redox transformation of1 has been proposed.

  3,6-二叔丁基邻苯醌 (1) 和 3,5-二叔丁基邻苯醌 (2) 与水-醇介质中的 NH3 以及与 (NH4)2CO3 中的相互作用已经研究了固相。介质亲核试剂参与的氧化还原过程发生在 1 中，而 2 与 NH3 在羰基上反应，转化为醌酰亚胺。已经提出了1的氧化还原转化机制。
• Synthesis of sterically hindered benzoquinone methacrylates
  作者：M. P. Shurygina、O. V. Markina、N. O. Druzhkov、T. I. Kulikova、A. V. Cherkasov、A. V. Piskunov、S. A. Chesnokov、V. K. Cherkasov

  DOI：10.1007/s11172-012-0165-8

  日期：2012.6

  Sterically hindered p- and o-benzoquinone methacrylates, viz., 2,5-di(tert-butyl)-3,6-di-oxocyclohexa-1,4-dienyl methacrylate and 2,5-di(tert-butyl)-3,4-dioxocyclohexa-1,5-dienyl methacrylate, were synthesized by O-acylation of the lithium and tetrabutylammonium salts of 3,6-di(tert-butyl)-2-hydroxy-p-benzoquinone with methacryloyl chloride. The influence of the nature of cation and solvent on regioselectivity of the acylation was studied. The o-benzoquinone derivative obtained can serve as a paramagnetic ligand in metal complexes.

  受立体阻碍的对苯醌和邻苯醌甲基丙烯酸酯，即2,5- 二（叔丁基）-3,6- 二氧代环己烷-1,4- 二烯基甲基丙烯酸酯和 2,5- 二（叔丁基）-3,4- 二氧代环己烷-1,5- 二烯基甲基丙烯酸酯是通过 3,6- 二（叔丁基）-2-羟基对苯醌的锂盐和四丁基铵盐与甲基丙烯酰氯的 O-酰化反应合成的。研究了阳离子和溶剂的性质对酰化反应区域选择性的影响。得到的邻苯醌衍生物可作为金属配合物中的顺磁配体。
• Coordination polymers based on CuII and MnII complexes with 2-hydroxy-3,6-di(tert-butyl)-1,4-benzoquinone
  作者：E. Yu. Fursova、V. I. Ovcharenko、E. V. Gorelik、G. V. Romanenko、A. S. Bogomyakov、V. K. Cherkasov、G. A. Abakumov

  DOI：10.1007/s11172-009-0148-6

  日期：2009.6

  The reactions of MnII and CuII ions with deprotonated 2-hydroxy-3,6-di(tert-butyl)-1,4-benzoquinone (L) afford bis(chelates) ML2. In the solid phases of the compounds, the coordinated ligands L perform the bridging function leading to the formation of polymer structures: layered in MnL2 and framework in CuL2. In the coordination units ML2 the chelate fragments are in the trans and cis positions relative

  MnII 和 CuII 离子与去质子化的 2-羟基-3,6-二(叔丁基)-1,4-苯醌 (L) 反应得到双（螯合物）ML2。在化合物的固相中，配位配体 L 执行桥接功能，导致聚合物结构的形成：层状在 MnL2 中，骨架在 CuL2 中。在配位单元 ML2 中，MnL2 和 CuL2 的螯合物片段分别处于反式和顺式位置。高温区有效磁矩分别为 5.85 和 1.91 μB 的聚合物结构 MnL2 和 CuL2 的顺磁性由金属离子决定，因为配位 L 的三重态能级位于根据计算数据，高于单线态。
• BLEACHING COMPOSITION
  申请人：Kao Corporation

  公开号：EP0447553A1

  公开（公告）日：1991-09-25

  A bleaching composition comprising: (a) hydrogen peroxide or a peroxide which generates hydrogen peroxide in an a aqueous solution thereof and (b) an organic peracid precursor which generates an organic peracid represented by general formula (I) upon reacting with component (a). In formula (I), wherein R1 represents a straight-chain or branched C1 to C5 alkyl or alkenyl group; R2 represents a straight-chain or branched C1 to C8 alkylene group, or a phenylene group which may be substituted with a straight-chain or branched C1 to Cs alkyl group; nA groups may be the same or different from one another and each represents a C2 to C4 alkylene group; and n is a number of 0 to 100.

  一种漂白组合物，包括：(a)过氧化氢或在其水溶液中生成过氧化氢的过氧化物；(b)有机过酸前体，与组分(a)反应后生成通式(I)代表的有机过酸。在式(I)中，其中 R1 代表直链或支链 C1 至 C5 烷基或烯基；R2 代表直链或支链 C1 至 C8 亚烷基，或可被直链或支链 C1 至 Cs 烷基取代的亚苯基；nA 基团可以彼此相同或不同，且各代表一个 C2 至 C4 亚烷基；n 是 0 至 100 的数字。