(2S)-2-(furan-3-yl)-2-trimethylsilyloxyacetonitrile | 851193-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (2S)-2-(furan-3-yl)-2-trimethylsilyloxyacetonitrile
• CAS: 851193-25-4
• 化学式: C₉H₁₃NO₂Si
• 分子量: 195.293
• InChiKey: CQXQETGXYYKVHK-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2S)-2-(furan-3-yl)-2-trimethylsilyloxyacetonitrile 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-cyano(3-furanyl)methyl acetate
  参考文献：
  名称：

  Chiral Lithium Binaphtholate Aqua Complex as a Highly Effective Asymmetric Catalyst for Cyanohydrin Synthesis

  摘要：

  A highly enantioselective cyanohydrin synthesis with aromatic aldehydes using chiral lithium binaphtholate aqua or alcohol complexes has been developed and is a simple and inexpensive catalyst suitable for process chemistry to give gram-scale cyanohydrins successfully. Dramatic improvements in enantiomeric excess have been realized along with an interesting changeover in absolute stereochemistry of cyanohydrin product against the thoroughly "dry" catalytic systems.

  DOI：

  10.1021/ja051125c
• 作为产物：
  描述：

  3-糠醛 、 三甲基氰硅烷 在 (R)-1,1'-Bi-2-naphthol 、 lithium isopropoxide 作用下， 以 甲苯 为溶剂， 反应 1.33h， 以96%的产率得到(2S)-2-(furan-3-yl)-2-trimethylsilyloxyacetonitrile
  参考文献：
  名称：

  Chiral Lithium Binaphtholate Aqua Complex as a Highly Effective Asymmetric Catalyst for Cyanohydrin Synthesis

  摘要：

  A highly enantioselective cyanohydrin synthesis with aromatic aldehydes using chiral lithium binaphtholate aqua or alcohol complexes has been developed and is a simple and inexpensive catalyst suitable for process chemistry to give gram-scale cyanohydrins successfully. Dramatic improvements in enantiomeric excess have been realized along with an interesting changeover in absolute stereochemistry of cyanohydrin product against the thoroughly "dry" catalytic systems.

  DOI：

  10.1021/ja051125c

文献信息

• Enantioselective Synthesis of Cyanohydrins by a Novel Aluminum Catalyst
  作者：Barry M. Trost、Silvia Martínez-Sánchez

  DOI：10.1055/s-2005-863716

  日期：——

  The development of a new chiral aluminum catalyst is reported. This catalyst has been applied efficiently to the asymmetric cyanosilylation of aldehydes.

  报道了一种新型手性铝催化剂的开发。该催化剂已有效地应用于醛的不对称氰基硅烷化。
• Chiral Lithium Binaphtholate Aqua Complex as a Highly Effective Asymmetric Catalyst for Cyanohydrin Synthesis
  作者：Manabu Hatano、Takumi Ikeno、Takashi Miyamoto、Kazuaki Ishihara

  DOI：10.1021/ja051125c

  日期：2005.8.1

  A highly enantioselective cyanohydrin synthesis with aromatic aldehydes using chiral lithium binaphtholate aqua or alcohol complexes has been developed and is a simple and inexpensive catalyst suitable for process chemistry to give gram-scale cyanohydrins successfully. Dramatic improvements in enantiomeric excess have been realized along with an interesting changeover in absolute stereochemistry of cyanohydrin product against the thoroughly "dry" catalytic systems.