(2RS,3RS)-3-hydroxy-3-phenyl-2-t-butylpropionitrile

• 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: (2RS,3RS)-3-hydroxy-3-phenyl-2-t-butylpropionitrile
• 英文别名: (2R)-2-[(R)-hydroxy(phenyl)methyl]-3,3-dimethylbutanenitrile
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: NYQUYQYXLHBGOR-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2RS,3RS)-3-hydroxy-3-phenyl-2-t-butylpropionitrile 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 threo-3-Hydroxy-2-tert-butyl-3-phenyl-propionsaeure-amid
  参考文献：
  名称：

  Canceill,J.; Jacques,J., Bulletin de la Societe Chimique de France, 1970, p. 2180 - 2187

  摘要：

  DOI：
• 作为产物：
  描述：

  2-bromo-3,3-dimethyl-butyronitrile 在 钾硼氢 作用下， 以 甲醇 为溶剂， 生成 (2RS,3RS)-3-hydroxy-3-phenyl-2-t-butylpropionitrile
  参考文献：
  名称：

  Canceill,J.; Jacques,J., Bulletin de la Societe Chimique de France, 1970, p. 2180 - 2187

  摘要：

  DOI：

文献信息

• Canceill,J.; Jacques,J., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1969, vol. 269, p. 239 - 240
  作者：Canceill,J.、Jacques,J.

  DOI：——

  日期：——
• Synthetic Optimization and Structural Limitations of the Nitrile Aldol Reaction
  作者：Paul R. Carlier、Kam Moon Lo、Michael M.-C. Lo、Priscilla C.-K. Lo、Cedric W.-S. Lo

  DOI：10.1021/jo9702148

  日期：1997.9.1

  In an effort to further optimize and to define the structural limitations of the nitrile aldol reaction, several studies were undertaken. Lithiated phenylacetonitrile 1 was demonstrated to exhibit diastereoselectivity for addition to benzaldehyde higher than that of other metalated phenylacetonitriles. With a view toward practical lab-scale synthesis of aldols derived from lithiated arylacetonitriles, the effects of reaction concentration and quenching method on isolated yields of the anti-aldols were readdressed. Secondary aldehydes give reasonable recrystallized yields of anti-aldols at reaction concentrations as high as 0.1 M; pivalaldehyde gives good results at concentrations up to 0.3 M. Thirdly, the aldol reaction of lithiated 1 with para-substituted benzaldehydes 6b-g was then studied; increasing electron-withdrawing power of the para substituent was found to cause a marked decrease in diastereaselectivity. Finally, the aldol reactions of two aliphatic nitriles (isovaleronitrile 4 and tert-butylacetonitrile 5, were studied. Suprisingly, aldol diastereoselectivity of aliphatic nitriles is not uniformly anti-selective, and selectivities overall are lower than those afforded by arylacetonitriles.
• Canceill,J.; Jacques,J., Bulletin de la Societe Chimique de France, 1970, p. 2180 - 2187
  作者：Canceill,J.、Jacques,J.

  DOI：——

  日期：——