2,4-二(溴甲基)-1,3,5-三甲基苯 | 55231-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,4-二(溴甲基)-1,3,5-三甲基苯
• 英文名称: 2,4-bis(bromomethyl)-1,3,5-trimethylbenzene
• 英文别名: 1,3-bis(bromomethyl)-2,4,6-trimethylbenzene；2,4-bis(bromomethyl)mesitylene；bis(bromomethyl)mesitylene；1,3-bis(bromomethyl)mesitylene；1,3-di(bromomethyl)-2,4,6-trimethylbenzene
• CAS: 55231-61-3
• 化学式: C₁₁H₁₄Br₂
• 分子量: 306.04
• InChiKey: WCSDNXZKHJSIMH-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  333.4±37.0 °C(Predicted)
• 密度：
  1.551±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,4-二(溴甲基)-1,3,5-三甲基苯 在 四(三苯基膦)钯 potassium phosphate 、 三氟化硼乙醚 、 cadmium(II) acetate 、 溶剂黄146 、 benzyltrimethylazanium tribroman-2-uide 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 氯苯 为溶剂， 反应 178.0h， 生成 2',4',6'-trimethyl-3',5'-bis(4-methyl-4,5-dihydrooxazol-2-yl)methylbiphenyl-2-ol
  参考文献：
  名称：

  Phenol-containing bis(oxazolines): synthesis and fluorescence sensing of amines

  摘要：

  The fluorescence sensing of primary amines as their neutral forms has been studied with bis(oxazolinyl)phenols (Me-BOP, Ph-BOP), which are efficiently synthesized starting from mesitylene in six steps and in overall 12-22% yields. The BOP sensors showed fluorescence enhancement toward butylamine and several arylethylamines, whereas they showed fluorescence quenching toward secondary and branched amines. The opposite fluorescence behavior is explained by an increased conformational restriction at the excited state, at which a proton transfer complex between the host and guest forms that is stabilized in a tripodal hydrogen bonding mode. This is the first example in which fluorescence enhancement is observed in amine sensing with phenolic fluorophores. Enantiomeric alpha-chiral organoamines were also sensed with different fluorescent intensity changes by Ph-BOP, complementing the previous tris(oxazolines) that sense enantiomeric alpha-chiral organoammonium ions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.060
• 作为产物：
  描述：

  聚合甲醛 、 均三甲苯 在 氢溴酸 、 溶剂黄146 作用下， 反应 8.0h， 以95%的产率得到2,4-二(溴甲基)-1,3,5-三甲基苯
  参考文献：
  名称：

  C3i对称八核镉笼：双阴离子模板合成，形成机理和性质

  摘要：

  一系列Ç 3我-对称双帽三角反棱柱镉8个笼[2X @镉8大号6（H 2 O）6 ] ⋅ Ñ  Ý ⋅溶剂（X =氯-，Y = NO 3 - ，Ñ = 2：MOCC ‐4 ; X = Br −，Y = NO 3 −，n = 2：MOCC‐5 ; X = NO 3 −，Y = NO 3 −，n = 2：MOCC‐6 ; X = NO 3 −，Y =高炉4 −，n = 2：MOCC-7 ; X = NO 3 -，Y = CLO 4 -，Ñ = 2：MOCC-8 ; X = CO 3 2-，n = 0：MOCC-9），由不同阴离子组成的双阴离子，是通过柔性配体溶剂热合成的。有趣的是，MOCC‐9的CO 3 2−模板是通过DMF溶剂的两步分解原位生成的。对于其他MOCC，球形或三角形单价阴离子也可以在其形成过程中发挥模板的作用。实验研究了这些阴离子在笼子中的模板能力，并首次进行了讨论。进行了MOCC

  DOI：

  10.1002/chem.201200980

文献信息

• Substituted 2-(2''-pyridyl)benzimidazole palladium(II) complexes as an efficient catalytic system for Suzuki--Miyaura cross-coupling reactions
  作者：Mahmut ULUSOY、Nurdal ÖNCEL、Emine AYTAR

  DOI：10.3906/kim-1505-105

  日期：——

  A new series of $N,N$-type 2-(2'-pyridyl)benzimidazole ligands (2A$_\mathbf1}}$, 2A$_\mathbf2}}$, 3B$_\mathbf1}}$, 3B$_\mathbf2}}$, 3B$_\mathbf3}}$, and 4C$_\mathbf1}})$ and their Pd(II) complexes (5A$_\mathbf1}}$, 5A$_\mathbf2}}$, 6B$_\mathbf1}}$, 6B$_\mathbf2}}$, 6B$_\mathbf3}}$, and 7C$_\mathbf1}})$ were prepared and characterized by conventional spectroscopic methods and elemental analyses. The incorporation of $N$-coordinated benzimidazole complexes of palladium gave high catalytic activity in the Suzuki-Miyaura coupling of aryl halides substrates. After determining the best active catalyst as 5A$_\mathbf1}}$, bearing the mesityl substituent on the benzimidazole ring with the Pd(II) ion, optimization studies were carried out via changing the substrate, base, time, atmosphere, and the effect of water. The DMF:H$_2}$O (4/1) and Cs$_2}$CO$_3}$ as base were found to be critical for the efficiency of the reaction yield (100%).

  制备了一系列新型$N,N$型2-(2'-吡啶基)苯并咪唑配体(2A$_\mathbf1}}$、2A$_\mathbf2}}$、3B$_\mathbf1}}$、3B$_\mathbf2}}$、3B$_\mathbf3}}$和4C$_\mathbf1}}$)及其Pd(II)配合物(5A$_\mathbf1}}$、5A$_\mathbf2}}$、6B$_\mathbf1}}$、6B$_\mathbf2}}$、6B$_\mathbf3}}$和7C$_\mathbf1}}$)，并通过常规光谱方法和元素分析进行了表征。含有$N$配位的苯并咪唑配体使得钯催化剂在Suzuki-Miyaura偶联反应中展现出极高的催化活性。在确定具有甲基苯并咪唑环结构的5A$_\mathbf1}}$为最佳活性催化剂后，通过改变底物、碱、时间、气氛和水等因素进行了优化研究。发现使用DMF:H$_2}$O (4/1)溶剂和Cs$_2}$CO$_3}$作为碱对反应产率（100%）的提高至关重要。
• Application of novel multi-cationic ionic liquids in microwave assisted 2-amino-4H-chromene synthesis
  作者：Arjun Kumbhar、Sanjay Jadhav、Rajendra Shejwal、Gajanan Rashinkar、Rajshri Salunkhe

  DOI：10.1039/c6ra01062h

  日期：——

  Novel multi-cationic ionic liquids containing a mesitylene backbone with acetate and methane sulphonate anions have been synthesized. These ionic liquids were used for the synthesis of 2-amino-4H-chromenes under microwave heating. The effects of nature and amount of ionic liquids on the yield and reaction time were thoroughly investigated. The ionic liquids showed a considerable level of reusability

  合成了含有均三甲苯骨架和乙酸根和甲磺酸根阴离子的新型多阳离子离子液体。这些离子液体用于在微波加热下合成2-氨基-4 H-苯甲基。彻底研究了离子液体的性质和数量对产率和反应时间的影响。离子液体显示出相当高的可重用性，而催化活性没有明显降低。我们已经成功地将微波技术的优势与离子液体相结合，以促进通过多组分策略从易得且廉价的材料中快速构建亚甲基骨架。
• Selective recognition of fluoride ions through fluorimetric and colorimetric response of a first mesitylene based dipodal sensor 15employing thiosemicarbazones
  作者：Sanyog Sharma、Maninder Singh Hundal、Geeta Hundal

  DOI：10.1016/j.tetlet.2013.03.003

  日期：2013.5

  chromo-fluorogenic anion sensor (2Z,2′Z)-2,2′-(((((2,4,6-trimethyl-1,3-phenylene)bis-(methyl-ene))bis-(oxy))bis(2,1-phenylene))bis(methanylylidene))bis(N-methylhydrazinecarbothio-amide) has been synthesized and characterized for the detection of F− ion in DMSO. The sensor has proven to be highly selective and sensitive to F− ion, moreover it can act as naked eye chromogenic sensor. The mechanism involved

  一种新的双臂色光荧光阴离子传感器（2 Ž，2' Ž）-2,2' - （（（（（2,4,6-三甲基-1,3-亚苯基）双- （甲基烯））二- （氧基））双（2,1-亚苯基））二（methanylylidene））双（ñ -methylhydrazinecarbothio酰胺）已被合成和表征用于检测的F -在DMSO中的离子。该传感器已被证明是高度选择性的和至F敏感-离子，而且它可以按肉眼生色传感器起作用。检测氟离子涉及的机制是–NH基团的去质子化，这通过使用TBAOH得以证实。所述双臂受体的预组织提供螯合氢键与球形˚F -离子。这些强大的氢键相互作用导致传感器快速去质子化，从而产生光学响应。只采用亚胺基团，的微弱的荧光能力1个通过在显示荧光增强表现为荧光传感器λ EX在添加的F 438纳米-离子。
• Paraoxonase Mimic by a Nanoreactor Aggregate Containing Benzimidazolium Calix and <scp>l</scp> ‐Histidine: Demonstration of the Acetylcholine Esterase Activity
  作者：Amanpreet Singh、Sanjeev Saini、Mayank、Navneet Kaur、Ajnesh Singh、Narinder Singh、Doo Ok Jang

  DOI：10.1002/chem.202004944

  日期：2021.3.26

  synthesize the benzimidazolium‐based calix compound R1⋅2 ClO4−. X‐ray crystallography analysis revealed that the hydrogen‐bonding interactions between the benzimidazolium cations and N,N‐dimethylformamide (DMF) helped R1⋅2 ClO4− encapsulate DMF molecule(s). A nanoreactor, with R1⋅2 ClO4− and l‐histidine (l‐His) as the components, was fabricated by using a neutralization method. The nanoreactor could detoxify

  阴离子介导preorganization方法被用于设计和合成基于苯并咪唑-杯化合物R1⋅ 2 CLO 4 - 。X射线晶体学分析表明，苯并咪唑阳离子之间的氢键相互作用Ñ，Ñ二甲基甲酰胺（DMF）帮助R1⋅ 2 CLO 4 -包封DMF分子（多个）。甲纳米反应器，与R1⋅ 2 CLO 4 -和升组氨酸（升-His）作为成分，通过使用中和方法制造。纳米反应器可以在30分钟内对对氧磷进行解毒。升‐他在这一过程中起着至关重要的作用。对氧磷酶是一种众所周知的用于农药降解的酶。Ellman试剂用于确定在存在纳米反应器的情况下对乙酰胆碱酯酶（AChE）活性的抑制百分比。结果表明，纳米反应器抑制了AChE的抑制。
• Benzene-based tripodal isothiouronium compounds as sulfate ion receptors
  作者：Hye Ran Seong、Dae-Sik Kim、Sung-Gon Kim、Heung-Jin Choi、Kyo Han Ahn

  DOI：10.1016/j.tetlet.2003.11.048

  日期：2004.1

  benzene-based tripodal isothiouronium receptors are synthesized for the selective recognition of tetrahedral oxoanions. The binding study by isothermal titration calorimetry indicates that the cationic receptors bind sulfate ions preferably in a tripodal mode, while they show a mixed binding mode toward phosphate ion. The tripodal isothiouronium receptors show large ΔG0 values toward sulfate ions in methanol

  合成了基于苯的新型三脚架异硫脲鎓受体，用于选择性识别四面体含氧阴离子。通过等温滴定热法进行的结合研究表明，阳离子受体优选以三脚架模式结合硫酸根离子，而它们显示出对磷酸根离子的混合结合模式。三脚架异硫脲鎓受体对甲醇中的硫酸根离子表现出较大的ΔG 0值，这是由熵驱动的。结果表明，微妙的结构约束可能导致结构相似的阴离子具有不同的键合模式。