2,6-bis(bromomethyl)-4-tert-butylphenol | 5011-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,6-bis(bromomethyl)-4-tert-butylphenol
• CAS: 5011-36-9
• 化学式: C₁₂H₁₆Br₂O
• 分子量: 336.066
• InChiKey: MWQHUBSMHIOWDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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

反应信息

• 作为反应物：
  描述：

  2,6-bis(bromomethyl)-4-tert-butylphenol 在 碘 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 69.0h， 生成 (28-Acetyloxy-5,17-ditert-butyl-10,24,25,27-tetraoxo-1,9,13,21-tetrazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-3,5,7(28),11,15(26),16,18,22-octaen-26-yl) acetate
  参考文献：
  名称：

  Heterocalixarenes. 1. Calix[2]uracil[2]arene:  Synthesis, X-ray Structure, Conformational Analysis, and Binding Character

  摘要：

  1,3-Bis[(1-uracilyl)methyl)]benzene derivatives 3, formed by selective N-1 alkylation of 1,3-bis(trimethylsilyloxy)pyrimidine with 1,3-bis(bromomethyl)benzene derivatives 2, on cyclization with the same or different derivative of 2, provide calix[2]uracil[2]arenes 4. Their conformations, investigated through X-ray, variable temperature H-1 NMR, and molecular modeling MM2 calculations, are found to depend on the nature of substituent(s) on the position 2 of 1,3-phenylene rings. 4a exists in equilibrium between various conformations, and 4b, 4d-4i adopt an inward flattened partial cone conformation. In 4j, the equilibrium is restricted to two conformations at -60 degrees C, but the 4j ethanol complex (2:1), in the solid state, has a cone conformation with ethanol being a H-bond donor through H of OH and CH2 and an acceptor through O of OH. 4d, 4j, and 4k exhibit significant preferences toward alkaline earth metal ions over alkali metal ions though overall bindings are poor.

  DOI：

  10.1021/jo990085q
• 作为产物：
  描述：

  4-叔-丁基-2,6-二(羟基甲基)苯酚 在 氢溴酸 、 溶剂黄146 作用下， 生成 2,6-bis(bromomethyl)-4-tert-butylphenol
  参考文献：
  名称：

  Vulcanization of butyl rubber by 2,6-di(acyloxymethyl)-4-hydrocarbyl phenols

  摘要：

  公开号：

  US02830970A1

文献信息

• Catalytic Asymmetric Cyano-Ethoxycarbonylation Reaction of Aldehydes Using a Novel <i>C</i>₂-Symmetric Chiral <i>N</i>,<i>N</i>′-Dioxide Titanium Complex
  作者：Xiaoming Feng、Qinghan Li、Lu Chang、Xiaohua Liu

  DOI：10.1055/s-2006-947322

  日期：2006.7

  The asymmetric addition of ethyl cyanoformate to a range of aldehydes was efficiently catalyzed by a easily prepared C 2 -symmetric chiral N,N'-dioxide-Ti(IV) complex in high yields with up to 90% ee under mild conditions. A linear effect between the enantiopurity of the ligand and the enantiopurity of the product was observed.

  氰基甲酸乙酯与一系列醛的不对称加成被一种易于制备的 C 2 -对称手性 N,N'-二氧化钛-Ti(IV) 配合物有效催化，在温和条件下的收率高达 90%。观察到配体的对映纯度和产物的对映纯度之间存在线性效应。
• (<i>o</i>-Hydroxyphenyl)methylphosphonic acids: Synthesis and potentiometric determinations of their p<i>K</i>_aValues
  作者：Volker Böhmer、Walter Vogt、Salah Chafaa、Jean Meullemeestre、Marie-José Schwing、François Vierling

  DOI：10.1002/hlca.19930760108

  日期：1993.2.10

  (o-Hydroxyphenyl)methylphosphonic acids are readily obtained from o-(bromomethyl)- or o-(hydroxymethyl)phenols and trialkyl phosphites. Subsequent hydrolysis leads to the corresponding phosphonic acids. For a series of such compounds, the pKa values have been determined by potentiometry. Their dependence on additional substituents in the aromatic ring is discussed in terms of electronic and steric

  从邻-（溴甲基）-或邻-（羟甲基）酚和亚磷酸三烷基酯容易获得（邻-羟基苯基）甲基膦酸。随后的水解产生相应的膦酸。对于一系列此类化合物，p K a值已通过电位计确定。根据电子和空间效应，讨论了它们对芳环中其他取代基的依赖性。
• Azolium-Linked Cyclophanes:  A Comprehensive Examination of Conformations by ¹H NMR Spectroscopy and Structural Studies
  作者：Murray V. Baker、Mark J. Bosnich、David H. Brown、Lindsay T. Byrne、Valerie J. Hesler、Brian W. Skelton、Allan H. White、Charlotte C. Williams

  DOI：10.1021/jo049097o

  日期：2004.10.1

  o/m-cyclophanes are rigid on the NMR time scale, as indicated by sharp 1H NMR spectra at all accessible temperatures. The non-mesitylene-based m-cyclophanes and the o-cyclophanes are fluxional on the NMR time scale at high temperatures, but in most cases, specific conformations can be “frozen out” at low temperatures. Many structures deduced from solution studies were consistent with those in the solid state

  报道了一系列偶氮连接的环烷的合成和表征。环烷由与两个苯环单元（苯，萘，对二甲苯，均三甲苯，1,2,3,4-和1,2,4， 5-四甲基苯，2,6-吡啶，和p -叔通过亚甲基基团丁基苯酚）。检查了在苯环类单元中含有邻位，间位和对位取代模式的环环烷。通过变温NMR研究在溶液中检查了环烷的构象，并且通过晶体学研究在固态下检查了环烷的构象。该P-环番，均三基如在所有可及温度下的1 H NMR清晰光谱所示，m-和o / m-环烷在NMR时标上是刚性的。非均三甲苯基米-cyclophanes和Ò -cyclophanes上在高温下的NMR时间尺度fluxional，但在大多数情况下，特定的构象可以是“冻结了”在低温下。由溶液研究得出的许多结构与固态结构一致。
• Coupling of Carbon Dioxide with Epoxides Efficiently Catalyzed by Thioether-Triphenolate Bimetallic Iron(III) Complexes: Catalyst Structure-Reactivity Relationship and Mechanistic DFT Study
  作者：Francesco Della Monica、Sai V. C. Vummaleti、Antonio Buonerba、Assunta De Nisi、Magda Monari、Stefano Milione、Alfonso Grassi、Luigi Cavallo、Carmine Capacchione

  DOI：10.1002/adsc.201600621

  日期：2016.10.20

  highly Lewis acidic catalysts. In combination with tetrabutylammonium bromide (TBAB) they are highly active catalysts in the synthesis of cyclic organic carbonates through the coupling of carbon dioxide to epoxides with the highest initial turnover frequencies reported to date for the conversion of propylene oxide to propylene carbonate for iron‐based catalysts (5200 h−1; 120 °C, 2 MPa, 1 h). In particular

  制备了一系列由硫醚-三酚盐配体支撑的双核铁（III）I配合物，以获得高度路易斯酸性的催化剂。与四丁基溴化铵（TBAB）结合使用时，它们是环状有机碳酸酯合成中的高活性催化剂，通过二氧化碳与环氧化物的偶联反应，迄今为止报道的最高周转频率是铁基环氧丙烷转化为碳酸丙烯酯的最高转换频率催化剂（5200 h -1; 120°C，2 MPa，1 h）。特别地，这些络合物显示出是用于将二氧化碳偶联至内部环氧乙烷的高度选择性的催化剂，其以良好的产率提供了相应的环状碳酸酯并且保留了初始立体化学构型。密度泛函理论（DFT）研究为这些Fe（III）配合物的相对较高的活性提供了一个合理的理由，显示了配体骨架中半不稳定的硫原子在促进反应性方面的基本作用。值得注意的是，尽管催化剂前体具有双核性质，但在催化循环中仅涉及一个金属中心。
• Calixarene/azolium cyclophane hybrids: synthesis, structure and conformations
  作者：Valerie J. Hesler、Brian W. Skelton、Allan H. White、David H. Brown、Murray V. Baker

  DOI：10.1007/s10847-015-0491-1

  日期：2015.6

  The synthesis, structure, and conformational behaviour of three imidazolium cyclophanes that incorporate one or two 4-tert-butylphenol or 4-tert-butylanisole groups as meta-disubstituted linkers in the macrocycle is described. The cyclophanes containing anisole moieties adopt a cone conformation in the solid state, which, in solution, is not labile on the NMR timescale. The cyclophanes containing one or two phenol moieties adopt conformations other than the cone in the solid state and are labile in solution on the NMR timescale. The phenol cyclophanes are readily deprotonated, and structural and conformational studies for a variety of the associated cyclophanes are also reported.

  描述了三种咪唑鎓环芳烃的合成、结构和构象行为，这些环芳烃在其巨型环中包含一个或两个作为间位双取代连接体的4-叔丁基苯酚或4-叔丁基苯醚基团。含有苯醚部分的环芳烃在固态时采用锥形构象，而在溶液中在NMR时间尺度上是稳定的。含有一个或两个苯酚部分的环芳烃在固态时采取除锥形以外的构象，并且在溶液中的NMR时间尺度上是可变的。苯酚环芳烃容易去质子，并且还报道了多种相关环芳烃的结构和构象研究。