carbonic acid allyl ester 4-methyl-2-oxo-pent-3-enyl-ester | 925462-39-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: carbonic acid allyl ester 4-methyl-2-oxo-pent-3-enyl-ester
• CAS: 925462-39-1
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: VTQGIDCUOFGEHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 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 4-methyl-2-oxo-pent-3-enyl-ester 、 叔丁基二甲基氯硅烷 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以66%的产率得到carbonic acid allyl ester 1-(tert-butyl-dimethyl-silanyloxymethylene)-3-methyl-but-2-enyl 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
• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 在 吡啶 、 sodium dihydrogenphosphate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 carbonic acid allyl ester 4-methyl-2-oxo-pent-3-enyl-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