4-cyanobenzoyl triethylsilane | 725270-27-9

• 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: 4-cyanobenzoyl triethylsilane
• 英文别名: 4-Triethylsilylcarbonylbenzonitrile
• CAS: 725270-27-9
• 化学式: C₁₄H₁₉NOSi
• 分子量: 245.396
• InChiKey: OEPXPCUARKHTFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苄基氰基甲酸酯 、 4-cyanobenzoyl 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)-(+)-benzyl 2-cyano-2-(4-cyano)phenyl-2-triethylsiloxyacetate 、 (R)-(-)-benzyl 2-cyano-2-(4-cyano)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
• 作为产物：
  描述：

  2-(4-cyano)phenyl-2-triethylsilyl-1,3-dithiane 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以35%的产率得到4-cyanobenzoyl triethylsilane
  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

文献信息

• 10.1021/acs.orglett.4c01782
  作者：Liu, Ying、Zhu, Zhihong、Zhang, Yunxiao、Zhang, Yizhi、Liu, Shanshan、Shen, Xiao

  DOI：10.1021/acs.orglett.4c01782

  日期：——

  emerging bench-stable reagents for the generation of electron-rich oxycarbenes that are difficult to access with unstable diazo compounds. Herein, we report a siloxycarbene-mediated stereoselective synthesis of silyl enol ethers through visible-light-induced intermolecular reactions between acylsilanes and α,β-unsaturated ketones. Both the solvent and low temperature are important for the success of the

  酰基硅烷是新兴的实验室稳定试剂，用于生成富电子的氧卡宾，而不稳定的重氮化合物难以获得这些氧卡宾。在此，我们报道了通过可见光诱导酰基硅烷和α,β-不饱和酮之间的分子间反应，硅氧卡宾介导的硅烯醇醚的立体选择性合成。溶剂和低温对于反应的成功都很重要。这种方法具有原子经济学、独特的立体控制和广泛的底物范围。该方法的合成潜力通过克级反应和各种下游转化（包括要求硅烯醇醚构型纯度的转化）得到证明。
• 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.