3-{[4-(tert-butyldimethylsilanyloxymethyl)phenyl]hydroxymethyl}benzonitrile | 928758-84-3

• 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-{[4-(tert-butyldimethylsilanyloxymethyl)phenyl]hydroxymethyl}benzonitrile
• 英文别名: 3-{[4-({[tert-Butyl(dimethyl)silyl]oxy}methyl)phenyl](hydroxy)methyl}benzonitrile；3-[[4-[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]-hydroxymethyl]benzonitrile
• CAS: 928758-84-3
• 化学式: C₂₁H₂₇NO₂Si
• 分子量: 353.536
• InChiKey: POXZZDRTMLYTBG-UHFFFAOYSA-N

物化性质

• 沸点：
  461.2±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-{[4-(tert-butyldimethylsilanyloxymethyl)phenyl]hydroxymethyl}benzonitrile 在 column Chiralpak AD 11 x 33 cm 作用下， 以 甲醇 、 乙醇 、 正庚烷 为溶剂， 反应 0.18h， 以829 g的产率得到(S)-3-((4-((tertbutyldimethylsilyloxy)methyl)phenyl)(hydroxy)methyl)benzonitrile
  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
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二溴乙烷 为溶剂， 反应 10.84h， 生成 3-{[4-(tert-butyldimethylsilanyloxymethyl)phenyl]hydroxymethyl}benzonitrile
  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

文献信息

• Optimized Catalytic Enantioselective Aryl Transfer Process Gives Access to mGlu2 Receptor Potentiators
  作者：Nicholas A. Magnus、Peter B. Anzeveno、D. Scott Coffey、David A. Hay、Michael E. Laurila、Jeffrey M. Schkeryantz、Bruce W. Shaw、Michael A. Staszak

  DOI：10.1021/op0602268

  日期：2007.5.1

  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.