| 104120-96-9

• CAS: 104120-96-9
• 化学式: C₁₄H₁₉NO₂Si
• 分子量: 261.396
• InChiKey: BWFIOQHPOUDOKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.25
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 、 水 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 2-(4-allyloxyphenyl)-2-hydroxyacetonitrile
  参考文献：
  名称：

  Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN

  摘要：

  We report a new thiourea-Bronsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enamioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) at the M06/6-31G(d,p) level of theory suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.

  DOI：

  10.1021/jo201864e
• 作为产物：
  描述：

  三甲基氰硅烷 、 4-烯丙氧基苯甲醛 在 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-(5-phenyl-1H-imidazol-1-yl)cyclohexyl)thiourea 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 60.0h， 生成
  参考文献：
  名称：

  Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN

  摘要：

  We report a new thiourea-Bronsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enamioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) at the M06/6-31G(d,p) level of theory suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.

  DOI：

  10.1021/jo201864e