bis(1-bromo-3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-yl) | 2179-38-6

• 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
• 英文名称: bis(1-bromo-3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-yl)
• 英文别名: 1,1'-Di-brom-3,5-3',5'-tetra-t-butyl-bis-cyclohexadien-(2.5.2'.5')-on-(4.4')；Bis-<1-brom-3,5-di-tert-butyl-4-oxo-2.5-cyclohexadien-yl-1>；4-Bromo-4-(1-bromo-3,5-ditert-butyl-4-oxocyclohexa-2,5-dien-1-yl)-2,6-ditert-butylcyclohexa-2,5-dien-1-one
• CAS: 2179-38-6
• 化学式: C₂₈H₄₀Br₂O₂
• 分子量: 568.432
• InChiKey: DLOWBIFSQMVLOQ-UHFFFAOYSA-N

物化性质

• 熔点：
  190-195 °C
• 沸点：
  561.0±50.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  bis(1-bromo-3,5-di-tert-butyl-4-oxo-2,5-cyclohexadien-1-yl) 以 氯仿 为溶剂， 生成 3,3',5,5'-四叔丁基-4,4'-联苯醌
  参考文献：
  名称：

  The reactions of an o-quinone monoimide with some phenols

  摘要：

  DOI：

  10.1021/jo00300a018
• 作为产物：
  描述：

  4-溴-2,6-二叔丁基苯酚 在 双氧水 、 碘 作用下， 以 甲醇 、 水 为溶剂， 以16%的产率得到3,3',5,5'-四叔丁基-4,4'-联苯醌
  参考文献：
  名称：

  A Mechanistic Approach to the Reaction of 2,6-Di-tert-butylphenol with an Iodinating Agent in Methanol:  Electrophilically Assisted Solvolysis of Intermediary 4-Iodocyclohexa-2,5-dienones

  摘要：

  Reactions of the title phenol (1) and of 4-iodophenol 2 with an iodinating agent, I-2 and H2O2, are conducted in MeOH for varying times with varying amounts of I-2, and the results are compared, The reaction of 1 gives 2, 4,4'-biphenol 3, 4,4'-diphenoquinone 4, 4-methoxyphenol 5, and p-benzoquinone 6, exclusively. The yields of the phenolic products (2, 3, and 5) vary with reaction time, but they disappear or almost disappear eventually, to make 4 and 6 the almost exclusive products, The reaction of 2 always gives 4 and 6 alone. In both of the reactions of 1 and of 2, employment of a higher initial It concentration not only completes the formation of 4 and 6 faster but also makes the final proportion of 6 higher. However, the ultimate yield of 6 from the reaction of 1 is significantly higher than that from the reaction of 2, irrespective of the initial I-2 concentration. These results are interpreted as follows. 4-Iodocyclohexa-2,5-dienone 12, the primary product of electrophilic iodination of 1, undergoes solvolysis (methanolysis), which is electrophilically assisted by I-2. The solvolysis of 12 can be so fast as to overwhelm its prototropic rearrangement to give 2. 4-Methoxycyclohexa-2,5-dienone 13, which is the primary product of the methanolysis of 12 and is suggested to be detectable by H-1 NMR spectroscopy, is converted into 6 via 5, Benzoquinone 6 can also arise from 4,4-diiodocyclohexa-2,5-dienone 7, the product of iodination of 2, by an analogous mechanism. The selectivity of the formation of 6 from 7 is low because the competing reaction, homolytic scission of the C-I bond in 7, predominates. The mechanism of the formation of 3 and 4 is also discussed.

  DOI：

  10.1021/jo951455n

文献信息

• Oxidation of phenols with iodine in alkaline methanol
  作者：Kanji Omura

  DOI：10.1021/jo00191a002

  日期：1984.8
• HEINE, HAROLD W.;CIACCIO, JAMES A.;CARSON, KENNETH G.;TAYLOR, CAROL M.;WI+, J. ORG. CHEM., 55,(1990) N3, C. 4039-4043
  作者：HEINE, HAROLD W.、CIACCIO, JAMES A.、CARSON, KENNETH G.、TAYLOR, CAROL M.、WI+

  DOI：——

  日期：——
• OMURA, KANJI, J. ORG. CHEM., 1984, 49, N 17, 3046-3050
  作者：OMURA, KANJI

  DOI：——

  日期：——