dipivaloylmethane monocyanohydrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dipivaloylmethane monocyanohydrin
• 英文别名: 2-Tert-butyl-2-hydroxy-5,5-dimethyl-4-oxohexanenitrile
• 化学式: C₁₂H₂₁NO₂
• 分子量: 211.304
• InChiKey: QZURAYOGRDLLGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2,6,6-四甲基-3,5-庚二酮 、 丙酮氰醇 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 480.0h， 以50%的产率得到dipivaloylmethane monocyanohydrin
  参考文献：
  名称：

  Automatic assembly of skeleton structures. 3. Stereoselective synthesis, stereochemistry, and cyclization ofd,l-?,?'-dioxy-?,?'-di-tert-butylglutaric acid

  摘要：

  Stereoselective synthesis of d,1-alpha,alpha'-dioxy-alpha,alpha'-di-tert-butylglutaric acid hydroxyiminolactonitrile (3) was conducted by the reaction of dipivaloylmethane with HCN in ether. The corresponding hydroxylacetonitrile (4) and amide (5), acid (6), and its ester (7), from which dilactone (8) was synthesized with preparative yields, were obtained from 3. Benzyl amide (9) was obtained by the reaction of 8 with BnNH2. The iminolactone structure 3 of dipivaloylmethane bis-cyanohyrin, the cis-pseudo-a orientation of the functional substituents in 3-7 and 9, and the structure of the dilactone 8 were confirmed by the H-1, C-13 NMR, IR and mass spectra.

  DOI：

  10.1007/bf00864186

文献信息

• Automatic assembly of skeleton structures. 3. Stereoselective synthesis, stereochemistry, and cyclization ofd,l-?,?'-dioxy-?,?'-di-tert-butylglutaric acid
  作者：I. V. Vystorop、Yu. N. El'natanov、R. G. Kostyanovskii

  DOI：10.1007/bf00864186

  日期：1992.7

  Stereoselective synthesis of d,1-alpha,alpha'-dioxy-alpha,alpha'-di-tert-butylglutaric acid hydroxyiminolactonitrile (3) was conducted by the reaction of dipivaloylmethane with HCN in ether. The corresponding hydroxylacetonitrile (4) and amide (5), acid (6), and its ester (7), from which dilactone (8) was synthesized with preparative yields, were obtained from 3. Benzyl amide (9) was obtained by the reaction of 8 with BnNH2. The iminolactone structure 3 of dipivaloylmethane bis-cyanohyrin, the cis-pseudo-a orientation of the functional substituents in 3-7 and 9, and the structure of the dilactone 8 were confirmed by the H-1, C-13 NMR, IR and mass spectra.