3,6-di-tert-butyl-4,5-(1,3-propanedioxy)-1,2-benzoquinone | 1310546-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 3,6-di-tert-butyl-4,5-(1,3-propanedioxy)-1,2-benzoquinone
• 英文别名: 6,9-di-tertbutyl-2,3-dihydrobenzo[b][1,4]dioxepine-7,8-dione；6,9-di-tert-butyl-3,4-dihydro-2H-1,5-benzodioxepine-7,8-dione；6,9-Di-t-butyl-3,4-dihydro-2h-1,5-benzodioxepine-7,8-dione；6,9-ditert-butyl-3,4-dihydro-2H-1,5-benzodioxepine-7,8-dione
• CAS: 1310546-12-3
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: HXESLLXVQCFKEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-di-tert-butyl-4,5-(1,3-propanedioxy)-1,2-benzoquinone 、 三苯基锑 以 甲苯 为溶剂， 以91%的产率得到(4,5-(propane-1,3-diolato)-3,6-ditert-butylcatecholato)triphenylantimony(V)
  参考文献：
  名称：

  基于邻醌，苯并[b] [1,4]-二恶英和苯并[b] [1,4]-二恶英的衍生物的三苯基锑（V）邻苯二酚

  摘要：

  摘要三苯基锑（V），（Etgly-3,6-DBCat）SbPh 3（I），（Propgly-3,6-DBCat）SbPh 3（II）和（Cat-3,6-DBCat）SbPh的新型儿茶酚盐配合物3（III）的基础上的空间位阻类似物3,6-二-叔丁基- ø苯醌，5,8-二-叔丁基-2,3-二氢苯并[ b ] [1,4]二氧杂环己烯6,7-二酮（L 1），6,9-二叔丁基-2,3-二氢苯并[ b ] [1,4]二氧杂松-7,8-二酮（L 2）和1,4-二-叔丁基-二苯并[ b，ë] [1,4] dioxine-2,3-dione（L 3），它们是2,3-二氢苯并[ b ] [1,4]二氧辛，2,3-二氢苯并[ b ] [1,4]二氧杂庚环分别合成了，和二苯并[1,4]二恶英衍生物。在室温下儿茶酚我和II用分子氧加入的O反应2分子以形成相应的spiroendoperoxides IV和 V。儿茶酚

  DOI：

  10.1134/s1070328419010093
• 作为产物：
  描述：

  3,6-二叔丁基环己-3,5-二烯-1,2-二酮 、 1,3-丙二醇 在 manganese(IV) oxide 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以19%的产率得到3,6-di-tert-butyl-4,5-(1,3-propanedioxy)-1,2-benzoquinone
  参考文献：
  名称：

  Multifunctional One-Dimensional Rhodium(I)–Semiquinonato Complex: Substituent Effects on Crystal Structures and Solid-State Properties

  摘要：

  Two new one-dimensional (1D) rhodium(I)-semiquinonato complexes formulated as [Rh(3,6-DBSQ-4,5-PDO)(CO)(2)](infinity) (4; 3,6-DBSQ-4,5-PDO center dot- = 3,6-di-tert-butyl-4,5-(1,3-propanedioxy)-1,2-benzosemiquinonato) and [Rh(3,6-DBSQ-4,5-(N,N'-DEN))(CO)(2)](infinity) (5; 3,6-DBSQ-4,5-(N,N'-DEN)(center dot-) = 3,6-di-tert-butyl-4,5-(N,N'-diethylenediamine)-1,2-benzosemiquinonato) were synthesized to explore the nature of the unusual structural phase transition and magnetic and conductive properties recently reported for [Rh(3,6-DBSQ-4,5-(MeO)(2))(CO)(2)](infinity) (3; 3,6-DBSQ-4,5-(MeO)(2)(center dot-) = 3,6-di-tert-butyl-4,5-dimethoxy-1,2-benzosemiquinonato). Their crystal structures and magnetic and conductive properties were investigated. Compounds 4 and 5 comprise neutral 1D chains of complex molecules stacked in a staggered arrangement with fairly short average Rh-Rh distances of 3.06 angstrom for 4 and 3.10 angstrom for 5. These distances are similar to those for 3 (3.09 angstrom); however, the molecules of 5 are strongly dimerized in the 1D chain. Compound 4 undergoes a first-order phase transition at Ttrs = 229.1 K, and its magnetic properties drastically change from antiferromagnetic coupling in the room-temperature (RT) phase to strong ferromagnetic coupling in the low-temperature (LT) phase. In addition, compound 4 exhibits a long-range ordering of net magnetic moments originating from the imperfect cancellation of antiferromagnetically coupled spins between the ferromagnetic 1D chains at TN = 10.9 K. Furthermore, this compound exhibits an interesting crossover from a semiconductor with a small activation energy (E-a = 31 meV) in the RT phase to a semiconductor with a large activation energy (E-a = 199 meV) in the LT phase. These behaviors are commonly observed for 3. Alternating current susceptibility measurements of 4, however, revealed a frequency-dependent phenomenon below 5.2 K, which was not observed for 3, thus indicating a slow spin relaxation process that possibly arises from the movements of domain walls. In contrast, compound 5, which possesses a strongly dimerized structure in its 1D chain, shows no sign of strong ferromagnetic interactions and is an insulator, with a resistivity greater than 7 x 10(7) Omega cm.

  DOI：

  10.1021/ic5019532

文献信息

• Alkoxylation of 3,6-di-tert-butyl-1,2-benzoquinone. New bis-1,2-benzoquinones
  作者：M. P. Shurygina、N. O. Druzhkov、M. V. Arsen’ev、M. P. Bubnov、G. K. Fukin、S. A. Chesnokov、V. K. Cherkasov

  DOI：10.1134/s1070428011040038

  日期：2011.4

  Alkoxylation of 3,6-di-tert-butyl-1,2-benzoquinone with a number of diols, including propane-1,3-diol, butane-1,4-diol, di-, and triethylene glycols, and cyclohexane-1,4-diyldimethanol, was studied. Nine new 4-alkoxy-3,6-di-tert-butyl-1,2-benzoquinones were synthesized, four of which were bis-1,2-benzoquinones with different tethers (6-13 atoms) between the quinone fragments. Depending on the length of the chain between the hydroxy groups in glycols, bicyclic 4,5-disubstituted 3,6-di-tert-butyl-1,2-benzoquinones were formed or their stepwise alkoxylation occurred. The newly synthesized o-benzoquinone derivatives can be reduced with alkali metals to give radical anions and converted into semiquinone chelates with manganese carbonyl.