carbonic acid allyl ester (Z)-2-(tert-butyldimethylsilanyloxy)-2-naphthalen-2-yl-vinyl ester | 925461-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: carbonic acid allyl ester (Z)-2-(tert-butyldimethylsilanyloxy)-2-naphthalen-2-yl-vinyl ester
• CAS: 925461-98-9
• 化学式: C₂₂H₂₈O₄Si
• 分子量: 384.547
• InChiKey: BDQAFGNKTIYECK-SILNSSARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  carbonic acid allyl ester (Z)-2-(tert-butyldimethylsilanyloxy)-2-naphthalen-2-yl-vinyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 0.33h， 生成 2-hydroxy-2-naphthalen-2-yl-pent-4-enal
  参考文献：
  名称：

  Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates

  摘要：

  Chiral alpha-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available alpha-halo or alpha-hydroxy ketones or enol silyl ethers with excellent yields and nantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity.

  DOI：

  10.1021/ja067342a
• 作为产物：
  描述：

  2-hydroxy-1-naphthalen-2-yl-ethanone 在 咪唑 、 四甲基乙二胺 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 carbonic acid allyl ester (Z)-2-(tert-butyldimethylsilanyloxy)-2-naphthalen-2-yl-vinyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates

  摘要：

  Chiral alpha-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available alpha-halo or alpha-hydroxy ketones or enol silyl ethers with excellent yields and nantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity.

  DOI：

  10.1021/ja067342a