(R)-2-allyl-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone | 925462-17-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (R)-2-allyl-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone
• 英文别名: (2R)-2-[tert-butyl(dimethyl)silyl]oxy-2-prop-2-enylcyclohexan-1-one
• CAS: 925462-17-5
• 化学式: C₁₅H₂₈O₂Si
• 分子量: 268.472
• InChiKey: RIWOGMKDIFFRPF-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-allyl-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 (R)-2-allyl-2-hydroxy-cyclohexanone
  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：

  carbonic acid allyl ester 2-oxo-cyclohexyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 12.5h， 生成 (R)-2-allyl-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexanone
  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

文献信息

• Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates
  作者：Barry M. Trost、Jiayi Xu、Markus Reichle

  DOI：10.1021/ja067342a

  日期：2007.1.1

  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.