4-溴-2,3,6-三甲基苯酚 | 51857-41-1

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 酚及其卤化、磺化、硝化或亚硝化衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-溴-2,3,6-三甲基苯酚
• 英文名称: 4-bromo-2,3,6-trimethylphenol
• 英文别名: 4-bromo-2,3,6-trimethyl phenol；2,3,6-trimethyl-4-bromophenol
• CAS: 51857-41-1
• 化学式: C₉H₁₁BrO
• 分子量: 215.09
• InChiKey: CNZUMQRUUPCHJR-UHFFFAOYSA-N

物化性质

• 沸点：
  277.2±35.0 °C(Predicted)
• 密度：
  1.406±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2908199090
• 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-溴-2,3,6-三甲基苯酚 在 palladium on activated charcoal 4-二甲氨基吡啶 、 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 氢气 、 叔丁基锂 、 硝酸 、 sodium acetate 、 potassium carbonate 、 对甲苯磺酸 、 三氟乙酸 、 三甲基乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.83h， 生成 methyl (E)-6-(2-amino-3-bromo-6-methoxy-4,5-dimethylphenyl)-4-methylhex-4-enoate
  参考文献：
  名称：

  Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid

  摘要：

  Structure-activity relationships in the region of the phthalide ring of the inosine monophosphate dehydrogenase inhibitor mycophenolic acid have been explored. Replacement of the lactone ring with other cyclic moieties resulted in loss of potency, especially for larger groups. Replacement of the ring by acyclic substituents also indicated a strong sensitivity to steric bulk. A phenolic hydroxyl group, with an adjacent hydrogen bond acceptor, was found to be essential for high potency. The aromatic methyl group was essential for activity; the methoxyl group could be replaced by ethyl to give a compound with 2-4 times the potency of mycophenolic acid in vitro and in vivo.

  DOI：

  10.1021/jm9603633
• 作为产物：
  描述：

  2,3,6-三甲基苯酚 在 Oxone 、 quartz 、 sodium bromide 作用下， 以 正庚烷 为溶剂， 反应 0.33h， 生成 4-溴-2,3,6-三甲基苯酚
  参考文献：
  名称：

  Aromatic substitution in ball mills: formation of aryl chlorides and bromides using potassium peroxomonosulfate and NaX

  摘要：

  芳基氯和芳基溴是通过在球磨机中使用KHSO5和NaX（X=Cl，Br）分别作为氧化剂和卤素源，从芳烃形成的。对反应参数的调查确定操作频率、研磨时间和研磨球数为主要影响变量，因为这些变量决定了向反应系统提供的能量。对液体辅助研磨条件的评估揭示，在这种特殊情况下，溶剂的添加没有优势效应。优先激活的芳烃被卤化，其中溴化得到的产物收率高于氯化。大多数反应具有区域选择性和化学选择性，因为更喜欢对位取代，而且没有观察到KHSO5对烷基化芳烃侧链的氧化作用。

  DOI：

  10.1039/c2gc16508b

文献信息

• A highly efficient approach to vanillin starting from 4-cresol
  作者：Jian-An Jiang、Cheng Chen、Ying Guo、Dao-Hua Liao、Xian-Dao Pan、Ya-Fei Ji

  DOI：10.1039/c4gc00003j

  日期：——

  A highly efficient approach to the famous flavor and fragrance compound vanillin has been developed starting from 4-cresol with the attention focused on improving the sustainability of all the reactions. The approach involves a three-step sequence of the quasi-quantitative selective clean oxybromination of 4-cresol, the high-yield selective aerobic oxidation of 2-bromo-4-cresol, and the quantitative methoxylation of 3-bromo-4-hydroxybenzaldehyde with the recovery of pure methanol. Herein, the pivotal oxidation and methoxylation reactions are logically investigated and developed into two concise methodologies. As a green alternative, the approach holds significant value for the sustainable manufacturing of vanillin.

  一种从4-甲酚出发制备著名香料与香精化合物香兰素的高效方法已被开发，该方法着重于提高所有反应的可持续性。该方法包括三个步骤的序列：准定量的选择性干净氧溴化4-甲酚、高产率的选择性需氧氧化2-溴-4-甲酚，以及定量的3-溴4-羟基苯甲醛甲氧基化并回收纯甲醇。在此，关键的氧化和甲氧基化反应被逻辑上研究和开发成两种简洁的方法。作为一种绿色替代方案，该方法对于香兰素的可持续制造具有重要价值。
• Catalytic Activation of Unstrained C(Aryl)–C(Alkyl) Bonds in 2,2′-Methylenediphenols
  作者：Jun Zhu、Yibin Xue、Rui Zhang、Benjamin L. Ratchford、Guangbin Dong

  DOI：10.1021/jacs.1c13342

  日期：2022.2.23

  unstrained and nonpolar C–C bonds remains a largely unmet challenge. Here, we describe our detailed efforts in developing a rhodium-catalyzed hydrogenolysis of unstrained C(aryl)–C(alkyl) bonds in 2,2′-methylenediphenols aided by removable directing groups. Good yields of the monophenol products are obtained with tolerating a wide range of functional groups. In addition, the reaction is scalable, and

  无应变和非极性 C-C 键的催化活化仍然是一个很大程度上未解决的挑战。在这里，我们描述了我们在开发铑催化氢解 2,2'-亚甲基二酚中无应变 C(芳基)-C(烷基)键的详细努力，并辅以可去除的定向基团。通过耐受广泛的官能团，获得了良好的单酚产品收率。此外，该反应具有可扩展性，催化剂负载量可降至 0.5 mol%。此外，该方法被证明可有效切割酚醛树脂和商用酚醛清漆树脂模型中的 C（芳基）-C（烷基）键。最后，详细的实验和计算机制研究表明，C-H 活化是一种竞争性但可逆的非循环反应，
• EP2 ANTAGONIST
  申请人：ONO Pharmaceutical Co., Ltd.

  公开号：EP3992176A1

  公开（公告）日：2022-05-04

  A drug is provided, which containing, as an active ingredient, a compound having an antagonistic activity against an EP2 receptor in the prevention and/or treatment of a disease associated with the activation of an EP2 receptor. A compound represented by general formula (I-A): (wherein all symbols have the same meanings as those described in the specification) or a pharmaceutically acceptable salt thereof is useful as a pharmaceutical ingredient having a potent antagonistic activity against an EP2 receptor in the prevention and/or treatment of a disease associated with the activation of an EP2 receptor.

  提供了一种药物，其包含作为活性成分的化合物，该化合物具有对EP2受体的拮抗活性，用于预防和/或治疗与EP2受体激活相关的疾病。通式（I-A）所表示的化合物（其中所有符号具有规范中描述的相同含义）或其药学上可接受的盐可用作具有强效EP2受体拮抗活性的药物成分，用于预防和/或治疗与EP2受体激活相关的疾病。
• Process for producing trimethyl-p-benzoquinone
  申请人：Sumitomo Chemical Company, Limited

  公开号：US03932475A1

  公开（公告）日：1976-01-13

  A process for producing trimethyl-p-benzoquinone by halogenating 2,3,5- or 2,3,6-trimethylphenol and oxidizing the resulting 2,3,5- or 2,3,6-trimethyl-4-halogenophenol, is disclosed. The resulting compound can readily be converted to trimethylhydroquinone useful as a starting material for producing vitamin E.

  本发明揭示了一种通过卤代2,3,5-或2,3,6-三甲基苯酚并氧化所得的2,3,5-或2,3,6-三甲基-4-卤代苯酚来生产三甲基对苯二酮的方法。所得化合物可以方便地转化为对生产维生素E有用的三甲基羟基苯醌的起始材料。
• Chiral phosphorous compounds
  申请人：Celtice Catalysts Limited, Nova UCD

  公开号：US08067642B2

  公开（公告）日：2011-11-29

  The present invention provides P-chiral compounds of general formulae (II) and (III): in formula (II) at least one of R21, R25, R26 and R30 is independently selected from CM alkyl, CF3, C1-4 alkoxy, phenyl and benzyloxy and the remaining substituents selected from R21, R25, R26 and R30 are hydrogen; at least one of R22, R24, R27 and R29 are independently selected from C1-14 alkyl, CF3, C1-14 alkoxy, phenyl and benzyloxy and the remaining substituents selected, from R22, R24, R27 and R29 are hydrogen; and R23 and R28 are independently selected from hydrogen, CM alkyl, CF3, C1-14 alkoxy, phenyl and benzyloxy; in formula (III) at least one of R21, R25, R26 and R30 is independently selected from phenyl and benzyloxy and the remaining substituents selected from R21, R25, R−26 and R30 are hydrogen; and R22, R−23 R24, R27, R28 and R29 are independently selected from hydrogen, C1-14 alkyl, CF3, C1-14 alkoxy, phenyl and benzyloxy.

  本发明提供了一般式（II）和（III）的P-手性化合物：在式（II）中，R21、R25、R26和R30中至少一个独立地选自CM烷基、CF3、C1-4烷氧基、苯基和苄氧基，其余取代基选自R21、R25、R26和R30为氢；R22、R24、R27和R29中至少一个独立地选自C1-14烷基、CF3、C1-14烷氧基、苯基和苄氧基，其余取代基选自R22、R24、R27和R29为氢；R23和R28独立地选自氢、CM烷基、CF3、C1-14烷氧基、苯基和苄氧基；在式（III）中，R21、R25、R26和R30中至少一个独立地选自苯基和苄氧基，其余取代基选自R21、R25、R-26和R30为氢；R22、R-23、R24、R27、R28和R29独立地选自氢、C1-14烷基、CF3、C1-14烷氧基、苯基和苄氧基。