3,5-di(3’,5’-di-t-butylphenyl)phenyl boronic acid | 501928-23-0

• 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: 3,5-di(3’,5’-di-t-butylphenyl)phenyl boronic acid
• 英文别名: [3,5-Bis(3,5-ditert-butylphenyl)phenyl]boronic acid
• CAS: 501928-23-0
• 化学式: C₃₄H₄₇BO₂
• 分子量: 498.557
• InChiKey: GCCPJZVJKKWZHM-UHFFFAOYSA-N

物化性质

• 沸点：
  601.8±65.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.89
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-di(3’,5’-di-t-butylphenyl)phenyl boronic acid 、 bis(2-(trimethylsilyl)ethyl) (R)-3,3'-dibromo-1,1'-binaphthyl-2,2'-dicarboxylate 在 potassium phosphate 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以55%的产率得到bis(2-(trimethylsilyl)ethyl)-(S)-3,3’-bis[3,5-(3’,5’-di-t-butylphenyl)phenyl]-1,1’-binaphthyl-2,2’-dicarboxylate
  参考文献：
  名称：

  Asymmetric Fluorolactonization with a Bifunctional Hydroxyl Carboxylate Catalyst

  摘要：

  We report the first successful example of a highly enantioselective fluorolactonization with an electrophilic fluorinating reagent, Selectfluor (R), in the presence of a novel bifunctional organocatalyst. The catalyst design includes a carboxylate anion functioning as a phase-transfer agent and a benzyl alcohol unit to capture the substrate through hydrogen bonding. Fluorinated isobenzofuranones were obtained in good yields with up to 94% ee (97:3 er). On the basis of mechanistic studies, we propose a unique reaction mechanism with potential for further applications.

  DOI：

  10.1021/jacs.5b06546
• 作为产物：
  描述：

  2-(3,3'',5,5''-tetra-tert-butyl-[1,1':3',1''-terphenyl]-5'-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine 、 硫酸 以 四氢呋喃 为溶剂， 以85%的产率得到3,5-di(3’,5’-di-t-butylphenyl)phenyl boronic acid
  参考文献：
  名称：

  Flexible, Bowl-Shaped N-Heterocyclic Carbene Ligands: Substrate Specificity in Iridium-Catalyzed Ketone Hydrosilylation

  摘要：

  A series of benzimidazolium chlorides was synthesized as precursors to N-heterocyclic carbene ligands, with N-substituents varying in size from 3,5-xylyl (1a) to first-generation dendritic 3,5-bis(3,5-di-tert-butylphenyl)phenyl (1b), to the second-generation 3,5-bis[3,5-bis(3,5-di-tert-butylphenyl)phenyl]phenyl (1c). The dendritic side groups of 1b and 1c form a flexible, bowl-like cavity. Iridium complexes of 1a-c were synthesized and were shown to be catalytically active for the hydrosilylation of aryl methyl ketones. The dendritic ligands 1b and 1c effect a moderate level of substrate specificity in the competitive hydrosilylation of ketones of varying size. In the competitive hydrosilylation of acetophenone versus 3-(3,5-di-tert-butylphenyl)acetophenone, acetophenone is consumed approximately 3.7 times more quickly using the second-generation ligand 1c. Using the control ligand la, this ratio is 1.8.

  DOI：

  10.1021/om800878m

文献信息

• Chiral Dienes as “Ligands” for Borane-Catalyzed Metal-Free Asymmetric Hydrogenation of Imines
  作者：Yongbing Liu、Haifeng Du

  DOI：10.1021/ja4025808

  日期：2013.5.8

  This paper describes a highly enantioselective metal-free hydrogenation of imines using chiral dienes as "ligands" for the generation of catalysts with HB(C6F5)2 by hydroboration in situ to furnish a variety of chiral amines with up to 89% ee, which provides a practical strategy for the development of novel chiral frustrated Lewis pairs for asymmetric hydrogenation.

  本文描述了使用手性二烯作为“配体”对亚胺进行高度对映选择性的无金属氢化，通过原位硼氢化反应生成具有 HB(C6F5)2 的催化剂，以提供各种手性胺，其 ee 高达 89%，从而提供开发用于不对称氢化的新型手性受阻路易斯对的实用策略。