4-Acetyl-5-(trimethylsilyl)veratrole | 169563-56-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Acetyl-5-(trimethylsilyl)veratrole
• 英文别名: 1-(4,5-Dimethoxy-2-trimethylsilylphenyl)ethanone
• CAS: 169563-56-8
• 化学式: C₁₃H₂₀O₃Si
• 分子量: 252.386
• InChiKey: MZVBXSOUZALMKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Acetyl-5-(trimethylsilyl)veratrole 在 sodium hydride 、 碳酸氢钠 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 14.67h， 生成 1-(tert-Butyldimethylsiloxy)-2-cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsilyl)phenyl)ethane
  参考文献：
  名称：

  A Highly Enantiocontrolled Strategy for the Synthesis of Benzylic Quaternary Carbon Centers. A Formal Total Synthesis of (-)-Mesembrine

  摘要：

  A remarkable substituent effect by a trimethylsilyl group was observed on the enantioselectivity of the tandem asymmetric epoxidation and enantiospecific ring expansion of 2-cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsiyl)phenyl)ethanol (24), affording (S)-(-)-2-(4,5-dimethoxy)-2-(trimethylsilyl)phenyl-2-(hydroxymethyl)cyclobutanone (25) in high enantiomeric excess. This feature enabled us to accomplish a concise and highly enantioselective total synthesis of(-)-mesembrine (1), providing a new and general strategy for the enantioselective synthesis of benzylic quaternary carbon centers.

  DOI：

  10.1021/jo00126a030
• 作为产物：
  描述：

  2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 在 重铬酸吡啶 、 4 A molecular sieve 、 水 、 sodium methylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 21.0h， 生成 4-Acetyl-5-(trimethylsilyl)veratrole
  参考文献：
  名称：

  A Highly Enantiocontrolled Strategy for the Synthesis of Benzylic Quaternary Carbon Centers. A Formal Total Synthesis of (-)-Mesembrine

  摘要：

  A remarkable substituent effect by a trimethylsilyl group was observed on the enantioselectivity of the tandem asymmetric epoxidation and enantiospecific ring expansion of 2-cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsiyl)phenyl)ethanol (24), affording (S)-(-)-2-(4,5-dimethoxy)-2-(trimethylsilyl)phenyl-2-(hydroxymethyl)cyclobutanone (25) in high enantiomeric excess. This feature enabled us to accomplish a concise and highly enantioselective total synthesis of(-)-mesembrine (1), providing a new and general strategy for the enantioselective synthesis of benzylic quaternary carbon centers.

  DOI：

  10.1021/jo00126a030

文献信息

• A Highly Enantiocontrolled Strategy for the Synthesis of Benzylic Quaternary Carbon Centers. A Formal Total Synthesis of (-)-Mesembrine
  作者：Hideo Nemoto、Tetsuro Tanabe、Keiichiro Fukumoto

  DOI：10.1021/jo00126a030

  日期：1995.10

  A remarkable substituent effect by a trimethylsilyl group was observed on the enantioselectivity of the tandem asymmetric epoxidation and enantiospecific ring expansion of 2-cyclopropylidene-2-(4,5-dimethoxy-2-(trimethylsiyl)phenyl)ethanol (24), affording (S)-(-)-2-(4,5-dimethoxy)-2-(trimethylsilyl)phenyl-2-(hydroxymethyl)cyclobutanone (25) in high enantiomeric excess. This feature enabled us to accomplish a concise and highly enantioselective total synthesis of(-)-mesembrine (1), providing a new and general strategy for the enantioselective synthesis of benzylic quaternary carbon centers.