3-hydroxy-3-(2-cyanophenyl)propanenitrile | 1369546-33-7

• 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: 3-hydroxy-3-(2-cyanophenyl)propanenitrile
• 英文别名: 2-(2-Cyano-1-hydroxyethyl)benzonitrile；2-(2-cyano-1-hydroxyethyl)benzonitrile
• CAS: 1369546-33-7
• 化学式: C₁₀H₈N₂O
• 分子量: 172.186
• InChiKey: WMCAKUAQVKCMNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲基硅烷氰化甲烷 、 2-氰基苯甲醛 在 tetra-n-butylammonium alginate 、 盐酸 、 水 作用下， 以 甲苯 、 甲醇 为溶剂， 反应 24.0h， 以58%的产率得到3-hydroxy-3-(2-cyanophenyl)propanenitrile
  参考文献：
  名称：

  Metal or ammonium alginates as Lewis base catalysts for the 1,2-addition of silyl nucleophiles to carbonyl compounds

  摘要：

  Several metal (Na+, Ca2+) or ammonium (n-Bu4N+) derivatives of alginic acid, an abundant bio-polymer obtained from the cell walls of brown algae, were synthesized. Their potential to act as organocatalysts to catalyze the 1,2-addition of various silyl derivatives to carbonyl compounds was evaluated for the first time. Ammonium alginate 1h is able to promote the reaction in modest to good isolated yields (up to 98%) affording access to a large range of substrates (beta-cyano alcohols or ester, beta-substituted methylacrylate or acrylonitrile, and cyanohydrin) by using only 5 mol % of catalyst. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.012

文献信息

• Metal or ammonium alginates as Lewis base catalysts for the 1,2-addition of silyl nucleophiles to carbonyl compounds
  作者：Cécile Verrier、Sylvain Oudeyer、Isabelle Dez、Vincent Levacher

  DOI：10.1016/j.tetlet.2012.02.012

  日期：2012.4

  Several metal (Na+, Ca2+) or ammonium (n-Bu4N+) derivatives of alginic acid, an abundant bio-polymer obtained from the cell walls of brown algae, were synthesized. Their potential to act as organocatalysts to catalyze the 1,2-addition of various silyl derivatives to carbonyl compounds was evaluated for the first time. Ammonium alginate 1h is able to promote the reaction in modest to good isolated yields (up to 98%) affording access to a large range of substrates (beta-cyano alcohols or ester, beta-substituted methylacrylate or acrylonitrile, and cyanohydrin) by using only 5 mol % of catalyst. (C) 2012 Elsevier Ltd. All rights reserved.