4,4-二溴-2,6-二叔丁基-2,5-CYLO己二烯ONE | 1144-36-1

• 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: 4,4-二溴-2,6-二叔丁基-2,5-CYLO己二烯ONE
• 英文名称: 4,4-dibromo-2,6-di-tert-butyl-2,5-cyclohexadienone
• 英文别名: 4,4-dibromo-2,6-di-tert-butylcyclohexa-2,5-dienone；4,4-dibromo-2,6-di-tert-butyl-cyclohexa-2,5-dienone；4,4-Dibrom-1-oxo-2,6-di-tert.-butyl-cyclohexadien-(2,5)；4,4-Dibrom-2,6-di-tert-butyl-cyclohexa-2,5-dien-1-on；4,4-Dibrom-2,6-di-tert-butyl-cyclohexa-2,5-dienon；4,4-Dibromo-2,6-di-tert-butyl-2,5-cyclohexadienon；4,4-dibromo-2,6-ditert-butylcyclohexa-2,5-dien-1-one
• CAS: 1144-36-1
• 化学式: C₁₄H₂₀Br₂O
• 分子量: 364.12
• InChiKey: WRRFKBTXZIRGSF-UHFFFAOYSA-N

物化性质

• 熔点：
  127-128 °C
• 沸点：
  335.2±42.0 °C(Predicted)
• 密度：
  1.485±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914700090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4,4-二溴-2,6-二叔丁基-2,5-CYLO己二烯ONE 在 硫酸 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以100%的产率得到2,6-二叔丁基苯醌
  参考文献：
  名称：

  Facile and convenient syntheses of quinones from phenols

  摘要：

  DOI：

  10.1021/jo00264a047
• 作为产物：
  描述：

  2,6-二叔丁基苯酚 在 溴 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 4,4-二溴-2,6-二叔丁基-2,5-CYLO己二烯ONE
  参考文献：
  名称：

  Rieker,A. et al., Zeitschrift fur Naturforschung. Teil B: Chemie, Biochemie, Biophysik, Biologie, 1969, vol. 24, p. 547 - 562

  摘要：

  DOI：
• 作为试剂：
  描述：

  十六醛 在 S-α,α-双(3,5-二三氟甲基苯基)脯氨醇三甲基硅醚 、 4,4-二溴-2,6-二叔丁基-2,5-CYLO己二烯ONE 、 苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  通过有机催化一锅策略实现分子复杂性—快速合成类鞘氨醇，氨基糖和多羟基化α-氨基酸的方法

  摘要：

  简单的复杂性：通过开发有机催化的手性离去基团策略，可以从简单的起始原料快速有效地实现分子的复杂性。4,5-二取代的异恶唑啉-N-氧化物产品是从有机催化的一锅三步程序中以高收率和对映选择性获得的，可作为天然产物的通用组成部分（请参见方案）。

  DOI：

  10.1002/anie.200901446

文献信息

• [EN] CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE alpha-HALO-CARBONYL COMPOUNDS<br/>[FR] SYNTHESE ASYMETRIQUE CATALYTIQUE DE COMPOSES DE DOLLAR G(A)-HALO-CARBONYLE OPTIQUEMENT ACTIFS
  申请人：HALLAND NIS

  公开号：WO2005080298A1

  公开（公告）日：2005-09-01

  A process for the catalytic asymmetric synthesis of an optically active compound of the formula (la) or (lb): wherein R is an organic group; X is halogen; Rl and R2which may the same or different represents H, or an organic group or Rl and R2 may be bridged together forming part of a ring system; R and R2 may be bridged together forming part of a ring system; with the provisio that R and Rl are different and R2, when different from H, is attached though a carbon-carbon bond, comprising the step of reacting a compound of the formula (2): with a halogenation agent in the presence of a catalytic amount of a chiral nitrogen containing organic compound.

  一种用于催化不对称合成光学活性化合物的方法，其化学式为(la)或(lb)：其中R是有机基团；X是卤素；R1和R2可以相同也可以不同，分别代表H，或者是有机基团，或者R1和R2可以通过形成环系统的桥连接在一起；R和R2可以通过形成环系统的桥连接在一起；在R和R1不同且R2与H不同时通过碳-碳键连接时，包括以下步骤：将化合物(2)与卤化试剂在含有含有手性氮的有机化合物的催化剂量的情况下反应。
• A Mechanistic Approach to the Reaction of 2,6-Di-<i>tert</i>-butylphenol with an Iodinating Agent in Methanol:  Electrophilically Assisted Solvolysis of Intermediary 4-Iodocyclohexa-2,5-dienones
  作者：Kanji Omura

  DOI：10.1021/jo951455n

  日期：1996.1.1

  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.
• MINISCI, FRANCESCO;CITTERIO, ATTILIO;VISMARA, ELENA;FONTANA, FRANCESCA;DE+, J. ORG. CHEM., 54,(1989) N, C. 728-731
  作者：MINISCI, FRANCESCO、CITTERIO, ATTILIO、VISMARA, ELENA、FONTANA, FRANCESCA、DE+

  DOI：——

  日期：——
• TASHIRO, MASASHI;ITOH, TAKASHI;FUKATA, GOUKI, REPTS RES. INST. IND. SCI. KYUSHU UNIV., 1984, N 77, 21-27
  作者：TASHIRO, MASASHI、ITOH, TAKASHI、FUKATA, GOUKI

  DOI：——

  日期：——
• CATALYTIC ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE ALPHA-HALO-CAR BONYL COMPOUNDS
  申请人：Cheminova A/S

  公开号：EP1716088A1

  公开（公告）日：2006-11-02