(S)-(-)-ethyl 2-cyano-2-(4-chloro)phenyl-2-triethylsiloxyacetate | 725270-35-9

• 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: (S)-(-)-ethyl 2-cyano-2-(4-chloro)phenyl-2-triethylsiloxyacetate
• 英文别名: (S)-(-)-ethyl 2-cyano-2-(4-chlorophenyl)-2-triethylsiloxyacetate；ethyl (2S)-2-(4-chlorophenyl)-2-cyano-2-triethylsilyloxyacetate
• CAS: 725270-35-9
• 化学式: C₁₇H₂₄ClNO₃Si
• 分子量: 353.921
• InChiKey: ZGSYTTJIHJNUBP-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(-)-ethyl 2-cyano-2-(4-chloro)phenyl-2-triethylsiloxyacetate 在 镍 甲基溴化镁 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 23.0 ℃ 、689.47 kPa 条件下， 反应 12.5h， 生成 (S)-(-)-3-phenyl-3-hydroxyazetidin-2-one
  参考文献：
  名称：

  Enantioselective Cyanation/Brook Rearrangement/C-Acylation Reactions of Acylsilanes Catalyzed by Chiral Metal Alkoxides

  摘要：

  New catalytic enantioselective cyanation/1,2-Brook rearrangement/C-acylation reactions of acylsilanes (4) with cyanoformate esters (7) are described. The products of the reaction are fully substituted malonic acid derivatives (8). Catalysts for this transformation were discovered via a directed candidate screen of 96 metal-ligand complexes. Optimization of a (salen)aluminum complex revealed significant remote electronic effects and concentration effects. The scope of the reaction was investigated by using a number of aryl acylsilanes and cyanoformate esters. Chemoselective reduction of the reaction products (8) afforded new enantioenriched alpha-hydroxy-alpha-aryl-beta-amino acid derivatives (32-34) and beta-lactams (35 and 36). This reaction provides a simple method for the construction of new nitrogen-containing enantioenriched chiral building blocks.

  DOI：

  10.1021/jo049164e
• 作为产物：
  描述：

  氰基甲酸乙酯 、 4-chlorobenzoyl triethylsilane 在 (1R,2R)-((E)-N=CH-[2-OH-3-(t-Bu)-5-Cl-phenyl])2-cyclohexane 、 aluminum isopropoxide 作用下， 以 甲苯 为溶剂， 反应 72.0h， 生成 (S)-(-)-ethyl 2-cyano-2-(4-chloro)phenyl-2-triethylsiloxyacetate 、 (R)-(+)-ethyl 2-cyano-2-(4-chloro)phenyl-2-triethylsiloxyacetate
  参考文献：
  名称：

  （甲硅烷氧基）腈阴离子的催化不对称酰化。

  摘要：

  DOI：

  10.1002/anie.200353354

文献信息

• Catalytic Asymmetric Acylation of (Silyloxy)nitrile Anions
  作者：David A. Nicewicz、Christopher M. Yates、Jeffrey S. Johnson

  DOI：10.1002/anie.200353354

  日期：2004.5.10
• Enantioselective Cyanation/Brook Rearrangement/<i>C</i>-Acylation Reactions of Acylsilanes Catalyzed by Chiral Metal Alkoxides
  作者：David A. Nicewicz、Christopher M. Yates、Jeffrey S. Johnson

  DOI：10.1021/jo049164e

  日期：2004.10.1

  New catalytic enantioselective cyanation/1,2-Brook rearrangement/C-acylation reactions of acylsilanes (4) with cyanoformate esters (7) are described. The products of the reaction are fully substituted malonic acid derivatives (8). Catalysts for this transformation were discovered via a directed candidate screen of 96 metal-ligand complexes. Optimization of a (salen)aluminum complex revealed significant remote electronic effects and concentration effects. The scope of the reaction was investigated by using a number of aryl acylsilanes and cyanoformate esters. Chemoselective reduction of the reaction products (8) afforded new enantioenriched alpha-hydroxy-alpha-aryl-beta-amino acid derivatives (32-34) and beta-lactams (35 and 36). This reaction provides a simple method for the construction of new nitrogen-containing enantioenriched chiral building blocks.