3,3'-Dibromo-5,5'-di-tert-butyl-4,4'-dimethoxy-2,2'-dimethyl-1,1'-biphenyl | 600172-56-3

• 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: 3,3'-Dibromo-5,5'-di-tert-butyl-4,4'-dimethoxy-2,2'-dimethyl-1,1'-biphenyl
• 英文别名: 3,3'-dibromo-5,5'-di-tert-butyl-4,4'-dimethoxy-2,2'-dimethylbiphenyl；3-Bromo-1-(3-bromo-5-tert-butyl-4-methoxy-2-methylphenyl)-5-tert-butyl-4-methoxy-2-methylbenzene；3-bromo-1-(3-bromo-5-tert-butyl-4-methoxy-2-methylphenyl)-5-tert-butyl-4-methoxy-2-methylbenzene
• CAS: 600172-56-3
• 化学式: C₂₄H₃₂Br₂O₂
• 分子量: 512.325
• InChiKey: UWDVBGCZUOQGKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  105-107 °C
• 沸点：
  484.8±45.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3'-Dibromo-5,5'-di-tert-butyl-4,4'-dimethoxy-2,2'-dimethyl-1,1'-biphenyl 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 偶氮二异丁腈 、 potassium carbonate 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 33.5h， 生成 N-(4S,5S)-5-(2,2-Dimethyl-4-phenyl-1,3-dioxanyl)-3,3'-bis-(3,5-(trifluoromethyl)-phenyl)-5,5'-di-tert-butyl-4,4'-dimethoxy-2,7-dihydrodibenzo[c,e]azepine
  参考文献：
  名称：

  Novel biphenyl organocatalysts for iminium ion-catalyzed asymmetric epoxidation

  摘要：

  Two novel chiral biphenyl iminium salts derived from L-acetonamine, containing electron-withdrawing 3,3'-substituents on the biphenyl unit, have been prepared and tested as asymmetric catalysts for epoxidation of prochiral alkenes. The results are compared with those achieved using the corresponding unsubstituted system. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.076
• 作为产物：
  描述：

  3,3'-Dibromo-5,5'-di-tert-butyl-4,4'-dihydroxy-2,2'-dimethyl-1,1'-biphenyl 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以98%的产率得到3,3'-Dibromo-5,5'-di-tert-butyl-4,4'-dimethoxy-2,2'-dimethyl-1,1'-biphenyl
  参考文献：
  名称：

  Synthesis and Evaluation of Chiral Dibenzazepinium Halide Phase-Transfer Catalysts

  摘要：

  已开发出两条制备手性二苯并氮杂卓季盐卤化物的互补路线。这使得合成并评估了一系列潜在的相转移催化剂（PTC），可用于涉及甘氨酸亚胺酯的不对称烷基化和迈克尔加成反应。

  DOI：

  10.1055/s-0028-1087810

文献信息

• Synthesis and Evaluation of Chiral Dibenzazepinium Halide Phase-Transfer Catalysts
  作者：Barry Lygo、Bryan Allbutt、Douglas Beaumont、Umar Butt、James Gilks

  DOI：10.1055/s-0028-1087810

  日期：2009.3

  Two complimentary routes to chiral dibenzazepinium halides have been developed. This has enabled the synthesis and evaluation of a range of potential phase-transfer catalysts (PTC) for asymmetric alkylation and Michael addition reactions involving glycine imine esters.

  已开发出两条制备手性二苯并氮杂卓季盐卤化物的互补路线。这使得合成并评估了一系列潜在的相转移催化剂（PTC），可用于涉及甘氨酸亚胺酯的不对称烷基化和迈克尔加成反应。
• Organocatalytic Enantioselective Decarboxylative Protonation Reaction of Meldrum's Acid Derivatives under PTC Conditions
  作者：Fabien Legros、Thomas Martzel、Jean-François Brière、Sylvain Oudeyer、Vincent Levacher

  DOI：10.1002/ejoc.201800331

  日期：2018.5.8

  An organocatalyzed enantioselective protonation sequence that starts from readily available disubstituted Meldrum's acid derivatives and phenols, proceeds under phase‐transfer‐catalytic (PTC) conditions, and provides chiral nonracemic 2‐aryl propionic esters in good isolated yields with up to 70 % ee is presented. The usefulness of this method was demonstrated by the synthesis of enantioenriched (S)‐ibuprofen

  一个organocatalyzed对映选择性质子化序列，从容易获得的二取代的麦德鲁姆酸衍生物与酚类，相转移催化（PTC）条件下进行，并开始提供手性非外消旋-芳基2与高达70％的良好的分离收率丙酸酯 EE呈现。富含对映体的（S）-布洛芬的合成证明了该方法的有效性。
• Identification of a highly effective asymmetric phase-transfer catalyst derived from α-methylnaphthylamine
  作者：Barry Lygo、Bryan Allbutt、S.Russell James

  DOI：10.1016/s0040-4039(03)01352-2

  日期：2003.7

  chiral amines with a series of conformationally dynamic biphenyl units. Screening of this library against the alkylation of a glycine imine has led to the identification of a highly effective asymmetric phase-transfer catalyst derived from α-methylnaphthylamine.

  季铵盐库是通过简单的手性胺与一系列构象动态的联苯单元反应生成的。针对甘氨酸亚胺的烷基化筛选该文库导致鉴定出衍生自α-甲基萘胺的高效不对称相转移催化剂。
• Novel biphenyl organocatalysts for iminium ion-catalyzed asymmetric epoxidation
  作者：Mohamed M. Farah、Philip C. Bulman Page、Benjamin R. Buckley、A. John Blacker、Mark R.J. Elsegood

  DOI：10.1016/j.tet.2012.10.076

  日期：2013.1

  Two novel chiral biphenyl iminium salts derived from L-acetonamine, containing electron-withdrawing 3,3'-substituents on the biphenyl unit, have been prepared and tested as asymmetric catalysts for epoxidation of prochiral alkenes. The results are compared with those achieved using the corresponding unsubstituted system. (c) 2012 Elsevier Ltd. All rights reserved.