[2-(1,3-Dioxolan-2-yl)-4,5-dimethoxyphenyl]-trimethylsilane | 169563-54-6

• 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: [2-(1,3-Dioxolan-2-yl)-4,5-dimethoxyphenyl]-trimethylsilane
• CAS: 169563-54-6
• 化学式: C₁₄H₂₂O₄Si
• 分子量: 282.412
• InChiKey: ODYSVMSMOPQEQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-(1,3-Dioxolan-2-yl)-4,5-dimethoxyphenyl]-trimethylsilane 在 重铬酸吡啶 、 4 A molecular sieve 、 水 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 15.17h， 生成 1-[1-(tert-Butyl-dimethyl-silanyloxy)-vinyl]-4,5-dimethoxy-2-trimethylsilanyl-benzene
  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：

  六甲基二硅烷 、 2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 在 sodium methylate 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 6.0h， 以56%的产率得到[2-(1,3-Dioxolan-2-yl)-4,5-dimethoxyphenyl]-trimethylsilane
  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

• Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids
  作者：Yasuyuki Kita、Mitsuhiro Arisawa、Michiyo Gyoten、Makiko Nakajima、Ryuji Hamada、Hirofumi Tohma、Takeshi Takada

  DOI：10.1021/jo9807868

  日期：1998.9.1

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.
• 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.