3,5-环己二烯-1,2-二酮,3-(1,1-二甲基乙基)-6-(1-甲基乙基)-(9CI) | 168331-80-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 3,5-环己二烯-1,2-二酮,3-(1,1-二甲基乙基)-6-(1-甲基乙基)-(9CI)
• 英文名称: 3-tert-butyl-6-isopropyl-1,2-benzoquinone
• 英文别名: 3-isopropyl-6-tert-butyl-o-benzoquinone；3-Tert-butyl-6-propan-2-ylcyclohexa-3,5-diene-1,2-dione
• CAS: 168331-80-4
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: HJLTVJJGWLAKRO-UHFFFAOYSA-N

物化性质

• 沸点：
  293.9±13.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-环己二烯-1,2-二酮,3-(1,1-二甲基乙基)-6-(1-甲基乙基)-(9CI) 在 KU-2-8 cation-exchange resin 、 硫酸 、 potassium hexacyanoferrate(III) 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 120.0h， 生成 5,5'-Di-tert-butyl-2,2'-diisopropyl-bicyclohexyl-1,5,1',5'-tetraene-3,4,3',4'-tetraone
  参考文献：
  名称：

  New sterically hindered di-o-quinones of the biphenyl series

  摘要：

  New di-o-quinones of the biphenyl series, namely, 2,2'-dialkyl-5,5'-di-tert-butylbiphenyl-3,4,3',4'-diquinones, were synthesized. Their structures were established by IR and NMR spectroscopy. The molecular structure of 2,2'-dimethyl-5,5'-di-tert-butylbiphenyl-3,4,3',4'-diquinone was established by X-ray structural analysis. The structure is characterized by orthogonal (the torsion angle is 82.9 degrees) mutual arrangement of o-benzoquinone fragments. ESR studies demonstrated that chemical reduction of diquinone proceeds in four one-electron stages to form paramagnetic mono- and trianions as intermediates. Quinopyrocatechols, which are intermediates in the synthesis of di-o-quinones, were isolated and characterized.

  DOI：

  10.1007/bf02495211
• 作为产物：
  描述：

  3,6-二叔丁基环己-3,5-二烯-1,2-二酮 、 二异丙基锌 在 盐酸 、 水 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 为溶剂， 生成 3,5-环己二烯-1,2-二酮,3-(1,1-二甲基乙基)-6-(1-甲基乙基)-(9CI) 、 2-isopropoxy-3,6-di-tert-butylphenol 、 4-isopropyl-3,6-di-tert-butyl-o-benzoquinone
  参考文献：
  名称：

  3,6-二叔丁基丁基苯醌与有机锌和有机镉化合物反应的研究

  摘要：

  取代基中的反应的效果3,6-二-叔丁基- о苯醌与有机锌和organocadmium化合物，导致三种类型的产品：3-烷基-6-叔丁基- о -benzoquinones，4-烷基-3,6-二-叔丁基- о -benzoquinones和2-烷氧基- （或2-苯氧基）-3,6-二-叔-butylphenols。相关分析提供了证据，表明第一类和第二类产物是通过亲核的1,2-和1,4-加成形成的，而取代的苯酚则是由单电子转移产生的。

  DOI：

  10.1134/s1070363216010072

文献信息

• Reaction on the addition of some organometallic compounds to 3,6-di-tert-butyl-o-benzoquinone: new o-quinones
  作者：G.A. Abakumov、V.K. Cherkasov、L.G. Abakumova、V.I. Nevodchikov、N.O. Druzhkov、N.P. Makarenko、Ju.A. Kursky

  DOI：10.1016/0022-328x(94)05168-b

  日期：1995.4

  interaction between organometallic R2M and carbonyl compounds. The reaction of organometallic compounds R2M with o-quinone, where R = Ph, Me, Et, Pr, 1Pr or tBu and M ≡ Zn, Cd, and Al, proceeds in two ways: (1) the single-electron oxidation of the organometallic compound by o-quinone, resulting in derivatives of alkyl(phenyl)oxyphenols; (2) the polar 1,2 and 1,4 addition of organometallic molecules to o-quinone

  3,6-二叔丁基-邻-苯并半醌对于研究有机金属R 2 M与羰基化合物之间的相互作用非常方便。有机金属化合物R 2 M与邻醌（其中R = Ph，Me，Et，Pr，1 Pr或t Bu与M≡Zn，Cd和Al的反应）以两种方式进行：（1）单有机金属化合物被邻醌电子氧化，生成烷基（苯基）氧基酚的衍生物；（2）将有机金属分子极性地1,2和1,4加到邻苯醌上形成共轭酮，在水解后产生羟基环己二酮。
• ——
  作者：S. A. Chesnokov

  DOI：10.1023/a:1023931428206

  日期：——

  Photoreduction of o-benzoquinones in the presence of p-bromo-N,N-dimethylaniline under irradiation (lambda > 500 nm) affords the corresponding pyrocatechols and hydroxyphenyl ethers. The latter are unstable and, in turn, decompose in the dark reaction to pyrocatechols. The ratio between pyrocatechol and hydroxyphenyl ether formed upon the photoreaction is determined by the structure of o-quinone, namely, the presence and bulk of substituents in positions 3 and 6 of the ring. The yield of pyrocatechol is maximal (60-65%) if the substituents are the same (H and H, Bu-t and Bu-t) or insignificantly differ (Pr-i and Bu-t), regardless of its bulk.
• Study of the reaction of 3,6-di-tert-butyl-о-benzoquinone with organozinc and organocadmium compounds
  作者：Yu. A. Kurskii、N. O. Druzhkov、A. N. Egorochkin、G. A. Abakumov

  DOI：10.1134/s1070363216010072

  日期：2016.1

  the reactions of 3,6-di-tert-butyl-о-benzoquinone with organozinc and organocadmium compounds, leading to three types of products: 3-alkyl-6-tert-butyl-о-benzoquinones, 4-alkyl-3,6-di-tert-butyl-о-benzoquinones, and 2-alkoxy-(or 2-phenoxy)-3,6-di-tert-butylphenols. Correlation analysis gave evidence to show that the first- and second-type products are formed by nucleophilic 1,2- and 1,4-addition, while

  取代基中的反应的效果3,6-二-叔丁基- о苯醌与有机锌和organocadmium化合物，导致三种类型的产品：3-烷基-6-叔丁基- о -benzoquinones，4-烷基-3,6-二-叔丁基- о -benzoquinones和2-烷氧基- （或2-苯氧基）-3,6-二-叔-butylphenols。相关分析提供了证据，表明第一类和第二类产物是通过亲核的1,2-和1,4-加成形成的，而取代的苯酚则是由单电子转移产生的。
• New sterically hindered di-o-quinones of the biphenyl series
  作者：G. A. Abakumov、V. I. Nevodchikov、N. O. Druzhkov、L. N. Zakharov、L. G. Abakumova、Yu. A. Kurskii、V. K. Cherkasov

  DOI：10.1007/bf02495211

  日期：1997.4

  New di-o-quinones of the biphenyl series, namely, 2,2'-dialkyl-5,5'-di-tert-butylbiphenyl-3,4,3',4'-diquinones, were synthesized. Their structures were established by IR and NMR spectroscopy. The molecular structure of 2,2'-dimethyl-5,5'-di-tert-butylbiphenyl-3,4,3',4'-diquinone was established by X-ray structural analysis. The structure is characterized by orthogonal (the torsion angle is 82.9 degrees) mutual arrangement of o-benzoquinone fragments. ESR studies demonstrated that chemical reduction of diquinone proceeds in four one-electron stages to form paramagnetic mono- and trianions as intermediates. Quinopyrocatechols, which are intermediates in the synthesis of di-o-quinones, were isolated and characterized.