2-(1,1-dimethylethyl)cyclohexanone oxime | 4500-18-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(1,1-dimethylethyl)cyclohexanone oxime
• 英文别名: 2-tert.butyl-cyclohexane-1-one oxime；N-(2-tert-butylcyclohexylidene)hydroxylamine
• CAS: 4500-18-9
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: LPCNUTNDTUFSDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1,1-dimethylethyl)cyclohexanone oxime 在 硫酸 作用下， 以20%的产率得到3-(1,1-dimethylethyl)hexahydro-2H-azepin-2-one
  参考文献：
  名称：

  Conformational Preferences in Hexahydro-2H-azepin-2-ones (Caprolactams)

  摘要：

  It was predicted and found that caprolactams are similar to cyclohexanes in conformational preferences. The compounds investigated were 7-methyl- and 3- and 7-(1,1-dimethylethyl)hexahydro-2H-azepin-2-ones. The 600-MHz NMR spectra showed discrete sets of axial and equatorial hydrogens, with the equatorial hydrogens lying ''downfield'' as in cyclohexane. The boat forms were surprisingly low in energy. The chair form with an axial substituent is predicted to have the highest energy of the four main conformers. Agreement between calculated and observed coupling constants is acceptable for tert-butyl-substituted caprolactams, but not for methyl (the energy of the axial methyl substituent appears to be too high in MM2 and especially in MM3). Some of these compounds show abnormally small coupling constants for hydrogens near the tert-butyl group. Calculations suggest that the effect is related to bond lengthening.

  DOI：

  10.1021/jo00090a019
• 作为产物：
  描述：

  2-叔-丁基环己酮 在 盐酸羟胺 作用下， 以 水 为溶剂， 反应 1.0h， 生成 2-(1,1-dimethylethyl)cyclohexanone oxime
  参考文献：
  名称：

  Conformational Preferences in Hexahydro-2H-azepin-2-ones (Caprolactams)

  摘要：

  It was predicted and found that caprolactams are similar to cyclohexanes in conformational preferences. The compounds investigated were 7-methyl- and 3- and 7-(1,1-dimethylethyl)hexahydro-2H-azepin-2-ones. The 600-MHz NMR spectra showed discrete sets of axial and equatorial hydrogens, with the equatorial hydrogens lying ''downfield'' as in cyclohexane. The boat forms were surprisingly low in energy. The chair form with an axial substituent is predicted to have the highest energy of the four main conformers. Agreement between calculated and observed coupling constants is acceptable for tert-butyl-substituted caprolactams, but not for methyl (the energy of the axial methyl substituent appears to be too high in MM2 and especially in MM3). Some of these compounds show abnormally small coupling constants for hydrogens near the tert-butyl group. Calculations suggest that the effect is related to bond lengthening.

  DOI：

  10.1021/jo00090a019

文献信息

• Benzoyl-ureas having acaricide and insecticide activity
  申请人：ISTITUTO GUIDO DONEGANI S.p.A.

  公开号：EP0211665B1

  公开（公告）日：1991-06-12
• Conformational Preferences in Hexahydro-2H-azepin-2-ones (Caprolactams)
  作者：Astrid Matallana、Albert W. Kruger、Charles A. Kingsbury

  DOI：10.1021/jo00090a019

  日期：1994.6

  It was predicted and found that caprolactams are similar to cyclohexanes in conformational preferences. The compounds investigated were 7-methyl- and 3- and 7-(1,1-dimethylethyl)hexahydro-2H-azepin-2-ones. The 600-MHz NMR spectra showed discrete sets of axial and equatorial hydrogens, with the equatorial hydrogens lying ''downfield'' as in cyclohexane. The boat forms were surprisingly low in energy. The chair form with an axial substituent is predicted to have the highest energy of the four main conformers. Agreement between calculated and observed coupling constants is acceptable for tert-butyl-substituted caprolactams, but not for methyl (the energy of the axial methyl substituent appears to be too high in MM2 and especially in MM3). Some of these compounds show abnormally small coupling constants for hydrogens near the tert-butyl group. Calculations suggest that the effect is related to bond lengthening.