syn-3-hydroxy-3-phenyl-2-propylpropionitrile

• 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: syn-3-hydroxy-3-phenyl-2-propylpropionitrile
• 英文别名: (2S)-2-[(R)-hydroxy(phenyl)methyl]pentanenitrile
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: CMJFIJJHWGTYFM-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-苯甲酰基戊腈 在 锂硼氢 、 cerium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (2R,1'R)-2-(1-hydroxy-1-phenylmethyl)pentanenitrile 、 syn-3-hydroxy-3-phenyl-2-propylpropionitrile
  参考文献：
  名称：

  An Efficient Diastereoselective Reduction of α-Alkyl-β-keto Carbonitriles with TiCl4/BH3 or LiBH4/CeCl3 to syn- or anti-α-Alkyl-β-hydroxy Carbonitriles

  摘要：

  alpha -Alkyl-beta -keto carbonitriles can be reduced stereoselectively to syn- and anti-alpha -alkyl-beta -hydroxy carbonitriles. The stereoselectivity can be explained in terms of properties of the Lewis acid employed. TiCl4 in noncoordinating solvents such as dichloromethane, followed by reduction with the borane/pyridine complex, predominantly led to the syrz-alpha -alkyl-beta -hydroxy carbonitriles, according to a chelate transition state, whereas CeCl3 in coordinating solvents such as THF, followed by reduction with LiBH4, predominantly led to the anti-isomers, in agreement with an open-chain transition state. The reduction to syn-alpha -alkyl-beta -hydroxy carbonitriles is the first general preparation of these compounds.

  DOI：

  10.1002/1099-0690(200108)2001:15<2971::aid-ejoc2971>3.0.co;2-k