γ,γ-Dimethyl-α-isopropyl-β-oxovaleronitrile | 77902-93-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: γ,γ-Dimethyl-α-isopropyl-β-oxovaleronitrile
• 英文别名: 4,4-Dimethyl-3-oxo-2-propan-2-ylpentanenitrile
• CAS: 77902-93-3
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: KNFYWQSRXBEHFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  γ,γ-Dimethyl-α-isopropyl-β-oxovaleronitrile 在 锂硼氢 、 cerium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以76%的产率得到anti-3-hydroxy-2-propyl-4,4-dimethylpentanenitrile
  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
• 作为产物：
  描述：

  2,2-二甲基-1-(1-吡咯烷基)-1-丙烷硫酮 、 1-cyano-2-methylpropyl trifluoromethanesulfonate 以80%的产率得到
  参考文献：
  名称：

  SHIOSAKI, KAZUMI;FELS, GREGOR;RAPOPORT, HENRY, J. ORG. CHEM., 1981, 46, N 16, 3230-3234

  摘要：

  DOI：

文献信息

• Versatile .beta.-ketoester and .beta.-ketonitrile synthesis through sulfide contraction
  作者：Kazumi Shiosaki、Gregor Fels、Henry Rapoport

  DOI：10.1021/jo00329a017

  日期：1981.7
• 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
  作者：Renato Dalpozzo、Giuseppe Bartoli、Marcella Bosco、Antonio De Nino、Antonio Procopio、Letizia Sambri、Antonio Tagarelli

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

  日期：2001.8

  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.
• SHIOSAKI, KAZUMI;FELS, GREGOR;RAPOPORT, HENRY, J. ORG. CHEM., 1981, 46, N 16, 3230-3234
  作者：SHIOSAKI, KAZUMI、FELS, GREGOR、RAPOPORT, HENRY

  DOI：——

  日期：——