carbonic acid (Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-vinyl ester cyclohex-2-enyl ester | 925462-20-0

• 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: carbonic acid (Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-vinyl ester cyclohex-2-enyl ester
• 英文别名: (Z)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-phenylvinyl cyclohex-2-en-1-yl carbonate；[(Z)-2-[tert-butyl(dimethyl)silyl]oxy-2-phenylethenyl] cyclohex-2-en-1-yl carbonate
• CAS: 925462-20-0
• 化学式: C₂₁H₃₀O₄Si
• 分子量: 374.552
• InChiKey: DQQCIVGLASHKNB-MNDPQUGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 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 (Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-vinyl ester cyclohex-2-enyl ester 在 四甲基乙二胺 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以776 mg的产率得到carbonic acid (Z)-2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-vinyl ester cyclohept-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：

  2-环己烯醇 在 四甲基乙二胺 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.83h， 生成 carbonic acid (Z)-2-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-vinyl ester cyclohex-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

文献信息

• The O-Acylation of Ketone Enolates by Allyl 1<i>H</i>-Imidazole-1-carboxylate Mediated with Boron Trifluoride EtherateA Convenient Procedure for the Synthesis of Substituted Allyl Enol Carbonates
  作者：Barry M. Trost、Jiayi Xu

  DOI：10.1021/jo7016313

  日期：2007.11.1

  A convenient access to substituted allyl enol carbonates was established through the reaction of ketone enolates with the complex of allyl 1H-imidazole-1-carboxylates and boron trifluoride etherate.

  通过酮烯醇化物与烯丙基 1 H-咪唑-1-羧酸酯和三氟化硼醚合物的配合物的反应，建立了对取代烯丙醇碳酸酯的便捷获取。
• 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.