carbonic acid allyl ester 2-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl ester | 925462-07-3

• 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 2-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl ester
• 英文别名: [2-[Tert-butyl(dimethyl)silyl]oxycyclohexen-1-yl] prop-2-enyl carbonate；[2-[tert-butyl(dimethyl)silyl]oxycyclohexen-1-yl] prop-2-enyl carbonate
• CAS: 925462-07-3
• 化学式: C₁₆H₂₈O₄Si
• 分子量: 312.481
• InChiKey: PFCXYKXGNQFXRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  carbonic acid allyl ester 2-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl 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 10.08h， 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：

  2-羟基环己酮二聚物 在 吡啶 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 carbonic acid allyl ester 2-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-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

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.