1-(3-allyl-2-butyl-2,3-dihydrobenzo[d]oxazol-2-yl)-1,1-difluoro-2-(trimethylsilyl)propan-2-ol | 1228184-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑啉
• 英文名称: 1-(3-allyl-2-butyl-2,3-dihydrobenzo[d]oxazol-2-yl)-1,1-difluoro-2-(trimethylsilyl)propan-2-ol
• 英文别名: 1-(2-Butyl-3-prop-2-enyl-1,3-benzoxazol-2-yl)-1,1-difluoro-2-trimethylsilylpropan-2-ol；1-(2-butyl-3-prop-2-enyl-1,3-benzoxazol-2-yl)-1,1-difluoro-2-trimethylsilylpropan-2-ol
• CAS: 1228184-50-6
• 化学式: C₂₀H₃₁F₂NO₂Si
• 分子量: 383.554
• InChiKey: MVGSIPXCUFAIDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-allyl-2-butyl-2,3-dihydrobenzo[d]oxazol-2-yl)-1,1-difluoro-2-(trimethylsilyl)propan-2-ol 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 1-(3-allyl-2-butyl-2,3-dihydrobenzo[d]oxazol-2-yl)-1-fluoropropan-2-one 、 1-(3-allyl-2-butyl-2,3-dihydrobenzo[d]oxazol-2-yl)-1-fluoropropan-2-one
  参考文献：
  名称：

  A rapid and convergent synthesis of α,α-difluoro-β-hydroxyketones through regiospecific defluorinative alkylation reaction

  摘要：

  Both the defluorinative alkylation reaction of trifluoroacetaldehyde N,O-acetals using alkyllithiums and the following C-C bond formation with carbonyls as electrophiles were accelerated by a suitable diamine additive such as (-)-sparteine to give alpha,alpha-difluoro-beta-hydroxyketone N,O-acetal products in an excellent yield. We also found that N-benzyl-N,O-acetal group of the resultant products can be removed under palladium-catalyzed hydrogenolysis conditions giving rise to the corresponding alpha,alpha-difluoro-beta-hydroxyketones. The present two-step procedure is a useful and novel synthetic approach for functionalized alpha,alpha-difluoroketones. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2010.03.018
• 作为产物：
  描述：

  正丁基锂 、 3-allyl-2-(trifluoromethyl)-2,3-dihydro-1,3-benzoxazole 、 1-(trimethylsilyl)ethanone 在 鹰爪豆碱 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 为溶剂， 反应 0.25h， 以82%的产率得到1-(3-allyl-2-butyl-2,3-dihydrobenzo[d]oxazol-2-yl)-1,1-difluoro-2-(trimethylsilyl)propan-2-ol
  参考文献：
  名称：

  A rapid and convergent synthesis of α,α-difluoro-β-hydroxyketones through regiospecific defluorinative alkylation reaction

  摘要：

  Both the defluorinative alkylation reaction of trifluoroacetaldehyde N,O-acetals using alkyllithiums and the following C-C bond formation with carbonyls as electrophiles were accelerated by a suitable diamine additive such as (-)-sparteine to give alpha,alpha-difluoro-beta-hydroxyketone N,O-acetal products in an excellent yield. We also found that N-benzyl-N,O-acetal group of the resultant products can be removed under palladium-catalyzed hydrogenolysis conditions giving rise to the corresponding alpha,alpha-difluoro-beta-hydroxyketones. The present two-step procedure is a useful and novel synthetic approach for functionalized alpha,alpha-difluoroketones. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2010.03.018

文献信息

• A rapid and convergent synthesis of α,α-difluoro-β-hydroxyketones through regiospecific defluorinative alkylation reaction
  作者：Hikaru Yanai、Tatsunori Ichikawa、Takeo Taguchi

  DOI：10.1016/j.tetlet.2010.03.018

  日期：2010.5

  Both the defluorinative alkylation reaction of trifluoroacetaldehyde N,O-acetals using alkyllithiums and the following C-C bond formation with carbonyls as electrophiles were accelerated by a suitable diamine additive such as (-)-sparteine to give alpha,alpha-difluoro-beta-hydroxyketone N,O-acetal products in an excellent yield. We also found that N-benzyl-N,O-acetal group of the resultant products can be removed under palladium-catalyzed hydrogenolysis conditions giving rise to the corresponding alpha,alpha-difluoro-beta-hydroxyketones. The present two-step procedure is a useful and novel synthetic approach for functionalized alpha,alpha-difluoroketones. (C) 2010 Published by Elsevier Ltd.