(S)-(tert-butyl-dimethylsilanyloxy)-2-cyclohexyl-2-phenyl-acetaldehyde | 925462-30-2

• 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: (S)-(tert-butyl-dimethylsilanyloxy)-2-cyclohexyl-2-phenyl-acetaldehyde
• 英文别名: (2S)-2-[tert-butyl(dimethyl)silyl]oxy-2-cyclohexyl-2-phenylacetaldehyde
• CAS: 925462-30-2
• 化学式: C₂₀H₃₂O₂Si
• 分子量: 332.558
• InChiKey: OKPAGSRABFBSMH-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  (S)-(tert-butyl-dimethylsilanyloxy)-2-cyclohexyl-2-phenyl-acetaldehyde 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 生成 (S)-2-环己基-2-苯基乙醇酸
  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：

  (2S)-2-[tert-butyl(dimethyl)silyl]oxy-2-cyclohex-2-en-1-yl-2-phenylacetaldehyde 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 以96%的产率得到(S)-(tert-butyl-dimethylsilanyloxy)-2-cyclohexyl-2-phenyl-acetaldehyde
  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