2,4,6-tris-[4-(tert-butyldimethylsilanyloxymethyl)phenyl]cyclotriboroxine | 889118-09-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 有机硼氧烷
• 英文名称: 2,4,6-tris-[4-(tert-butyldimethylsilanyloxymethyl)phenyl]cyclotriboroxine
• 英文别名: {1,3,5,2,4,6-Trioxatriborinane-2,4,6-triyltris[(4,1-phenylene)methyleneoxy]}tris[tert-butyl(dimethyl)silane]；[4-[4,6-bis[4-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]-1,3,5,2,4,6-trioxatriborinan-2-yl]phenyl]methoxy-tert-butyl-dimethylsilane
• CAS: 889118-09-6
• 化学式: C₃₉H₆₃B₃O₆Si₃
• 分子量: 744.615
• InChiKey: CARMTALYHBTNGW-UHFFFAOYSA-N

物化性质

• 沸点：
  640.9±65.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-氰基苯甲醛 、 2,4,6-tris-[4-(tert-butyldimethylsilanyloxymethyl)phenyl]cyclotriboroxine 在 diethylzinc 、 (R)-(-)-2-哌啶-1,1,2-三苯基乙醇 作用下， 以 甲苯 为溶剂， 生成 (S)-3-((4-((tertbutyldimethylsilyloxy)methyl)phenyl)(hydroxy)methyl)benzonitrile
  参考文献：
  名称：

  Diarylketone Ketoreductase Screen and Synthesis Demonstration to Access mGlu2 Receptor Potentiators

  摘要：

  This communication describes proof of concept for an enantioselective enzyme-based synthesis of diarylmethanol (S)-1 to access mGlu2 receptor potentiators. A ketoreductase (KRED) screen was applied to benzophenone 8 to afford chiral diarylmethanol (S)-9, which is a useful intermediate for the preparation of chiral diarylmethanol (S)-1. In addition, a more practical synthesis of benzophenone 8 was demonstrated utilizing Friedel Crafts acylation and radical bromination chemistry.

  DOI：

  10.1021/op2002479
• 作为产物：
  描述：

  4-溴苄醇 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.16h， 生成 2,4,6-tris-[4-(tert-butyldimethylsilanyloxymethyl)phenyl]cyclotriboroxine
  参考文献：
  名称：

  Optimized Catalytic Enantioselective Aryl Transfer Process Gives Access to mGlu2 Receptor Potentiators

  摘要：

  An asymmetric enantioselective aryl transfer reaction was developed to give access to the diarylmethanol 7 and ultimately acetate 2 which is useful for the preparation of mGlu2 receptor potentiators ( Scheme 3). The aryl transfer chemistry involved the preparation of a proposed arylalkylzinc species 14 from boroxine 16 and diethylzinc (DEZ), and reacting this mixture with aldehyde 5 in the presence of chiral ligand 15. During the course of optimizing the preparations of proposed intermediate 14 and diarylmethanol 7, an understanding of optimal stoichiometry and reaction times was gained through empirical observation, the use of solution IR, and analyzing off-gases via real time gas analysis/mass spectroscopy. The preparation of diarylmethanol 7 and subsequent conversion into acetate 2 required carefully selected workups, selective extractions, and azeotropic distillations to generate a series of stock solutions to accommodate oil intermediates that finally gave acetate 2 as a crystalline solid with > 99% ee.

  DOI：

  10.1021/op0602268