2,6-dibromo-3,5-dimethylphenol | 83385-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,6-dibromo-3,5-dimethylphenol
• CAS: 83385-86-8
• 化学式: C₈H₈Br₂O
• 分子量: 279.959
• InChiKey: XLQZZIWSAWDWJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-dibromo-3,5-dimethylphenol 在 cesium fluoride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  苯 1,2,4-三取代和脱芳基 1,2,4-三官能化

  摘要：

  苄的 1,2,4-三取代和脱芳基 1,2,4-三官能化均由带有五-2,4-二烯-1-基部分的亚砜完成。这些级联转化通过苯炔插入 S=O 键和不常见的区域特异性阴离子 [4,5]-σ 重排进行，在 C1-、C2- 上提供 C-O、C-S 和 C-C 键, 和苯环的 C4 位，分别。该研究展示了新的级联苯炔反应模式，包括远端 C-H 键功能化和脱芳构化。

  DOI：

  10.1021/jacs.1c04389
• 作为产物：
  描述：

  3,5-二甲基苯酚 在 N-Brom-tert.-butylamin 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以90%的产率得到2,6-dibromo-3,5-dimethylphenol
  参考文献：
  名称：

  苯 1,2,4-三取代和脱芳基 1,2,4-三官能化

  摘要：

  苄的 1,2,4-三取代和脱芳基 1,2,4-三官能化均由带有五-2,4-二烯-1-基部分的亚砜完成。这些级联转化通过苯炔插入 S=O 键和不常见的区域特异性阴离子 [4,5]-σ 重排进行，在 C1-、C2- 上提供 C-O、C-S 和 C-C 键, 和苯环的 C4 位，分别。该研究展示了新的级联苯炔反应模式，包括远端 C-H 键功能化和脱芳构化。

  DOI：

  10.1021/jacs.1c04389

文献信息

• Synthesis of a New Chiral Sulfonic Acid
  作者：Jérôme Blanchet、Joydeb Das、Fabien Le Cavelier、Jacques Rouden

  DOI：10.1055/s-0031-1290753

  日期：2012.5

  available phenol, followed by a Newman–Kwart rearrangement. Resolution by preparative chiral HPLC and oxidative cleavage give the targeted Brønsted acid in >99% ee. A convenient route to an original chiral sulfonic acid is disclosed. The synthesis is based on an optimized and regioselective direct bis-orthoarylation of a commercially available phenol, followed by a Newman–Kwart rearrangement. Resolution

  摘要 公开了获得原始手性磺酸的简便方法。合成是基于对市售苯酚的优化和区域选择性直接双原位芳构化，然后进行纽曼-科沃特重排。通过制备型手性HPLC拆分和氧化裂解可得到目标99％ee的布朗斯台德酸。 公开了获得原始手性磺酸的简便方法。合成是基于对市售苯酚的优化和区域选择性直接双原位芳构化，然后进行纽曼-科沃特重排。通过制备型手性HPLC拆分和氧化裂解可得到目标99％ee的布朗斯台德酸。
• Restricted Rotation Involving the Tetrahedral Carbon. XLIII. Buttressing Effect on Rotational Barriers in Bromine-substituted 9-(2-Methoxy-4,6-dimethylphenyl)fluorenes
  作者：Masahiro Aoki、Mikio Nakamura、Michinori Oki

  DOI：10.1246/bcsj.55.2512

  日期：1982.8

  or two bromo groups on the phenyl ring were prepared and the buttressing effect on the rotational barrier about the C9–Cph bond were investigated. The free energies of activation for rotation were 26.5, 25.9, and 27.2 kcal/mol at 56 °C for 3-bromo, 5-bromo, and 3,5-dibromo compounds, respectively. The buttressing effect was enhanced when the bromo group was next to the methoxyl group relative to that

  制备了在苯环上带有一个或两个溴基团的 9-(2-Methoxy-4,6-二甲基苯基)芴，并研究了对围绕 C9-Cph 键的旋转势垒的支撑作用。在 56 °C 下，3-溴、5-溴和 3,5-二溴化合物的旋转活化自由能分别为 26.5、25.9 和 27.2 kcal/mol。当溴基团与甲氧基相对于甲基基团紧邻时，支撑作用增强。结果归因于这样一个事实，即在正常情况下通过氧原子产生空间效应的甲氧基必须采取构象，而不是与苯环共面，这是由溴基团的存在引起的。
• 2,6-Bis(2-alkylphenyl)-3,5-dimethylphenol as a New Chiral Phenol with <i>C</i>₂-Symmetry. Application to the Asymmetric Alkylation of Aldehydes
  作者：Susumu Saito、Taichi Kano、Keiko Hatanaka、Hisashi Yamamoto

  DOI：10.1021/jo970747g

  日期：1997.8.1
• Understanding Solid/Solid Organic Reactions
  作者：Gadi Rothenberg、Andrew P. Downie、Colin L. Raston、Janet L. Scott

  DOI：10.1021/ja0034388

  日期：2001.9.1

  The concept of an organic reaction between two macroscopic solid particles is investigated. Thus, we study several reactions that have been recently reported to proceed "in the solid phase" and clearly show that, in most cases, grinding the two solid reactants together results in the formation of a liquid phase. This is true both for catalytic transformations (e.g., aldol condensations and oligomerization of benzylic compounds) and for noncatalytic reactions (Baeyer-Villiger oxidations, oxidative coupling of naphthols using iron chloride, condensation of amines and aldehydes to form azomethines, homo-etherification of benzylic alcohols using p-toluenesulfonic acid, and nuclear aromatic bromination with NBS). This liquefaction implies the existence of a eutectic mixture with T-fusion below ambient temperature (although both reagents have higher than ambient melting points). In cases where heating is required, it is again clear that a phase change (from solid to liquid) occurs, explaining the observed reaction kinetics. On the basis of 19 experimental examples, we discuss the possibility of solid-phase organic reactions and the implications of these findings to the reaction between two solid reagents. A general description of such reactive systems is proposed. based on a consideration of the potential for eutectic (or peritectic) formation between the constituents of the liquid phases that arise during the process of mechanical mixing of the solid reagents and products.
• Jonkheer,P.C.T.M. et al., Recueil des Travaux Chimiques des Pays-Bas, 1978, vol. 97, p. 223 - 248
  作者：Jonkheer,P.C.T.M. et al.

  DOI：——

  日期：——