3-Methyl-4,5-cyclohexyl-4-oxazolin-2-one | 98593-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Methyl-4,5-cyclohexyl-4-oxazolin-2-one
• 英文别名: 3-methyl-4,5,6,7-tetrahydro-3H-benzoxazol-2-one；3-Methyl-4,5,6,7-tetrahydro-3H-benzoxazol-2-on；3-Methyl-4,5,6,7-tetrahydro-1,3-benzoxazol-2-one
• CAS: 98593-30-7
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: SDBYMGHFEIYZDL-UHFFFAOYSA-N

物化性质

• 沸点：
  231.6±23.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Methyl-4,5-cyclohexyl-4-oxazolin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 异辛烷 为溶剂， 反应 5.0h， 以84%的产率得到3-Methyl-4,5-cyclohexyl-4,5-cis-dihydro-4-oxazolin-2-one
  参考文献：
  名称：

  Reaction of oximes with dimethyl carbonate: a new entry to 3-methyl-4,5-disubstituted-4-oxazolin-2-ones

  摘要：

  The reaction of ketone oximes with dimethyl carbonate (DMC) carried out in an autoclave at 180-190-degrees-C and in the presence of K2CO3 yields 3-methyl-4,5-disubstituted-4-oxazolin-2-ones. The reaction can be applied to both aliphatic and aromatic ketone oximes, provided that a methylene group be present near the C=N bond. Nonoptimized yields range from 22 to 48%. The reaction seems to be a [3,3] sigmatropic rearrangement where DMC plays a key role in causing the initial N-methylation of the oximes.

  DOI：

  10.1021/jo00073a041
• 作为产物：
  描述：

  环己酮肟 、 碳酸二甲酯 在 potassium carbonate 作用下， 反应 7.25h， 以48%的产率得到3-Methyl-4,5-cyclohexyl-4-oxazolin-2-one
  参考文献：
  名称：

  Reaction of oximes with dimethyl carbonate: a new entry to 3-methyl-4,5-disubstituted-4-oxazolin-2-ones

  摘要：

  The reaction of ketone oximes with dimethyl carbonate (DMC) carried out in an autoclave at 180-190-degrees-C and in the presence of K2CO3 yields 3-methyl-4,5-disubstituted-4-oxazolin-2-ones. The reaction can be applied to both aliphatic and aromatic ketone oximes, provided that a methylene group be present near the C=N bond. Nonoptimized yields range from 22 to 48%. The reaction seems to be a [3,3] sigmatropic rearrangement where DMC plays a key role in causing the initial N-methylation of the oximes.

  DOI：

  10.1021/jo00073a041

文献信息

• The Direct Introduction of Carbonates α to Carbonyl Groups
  作者：Nicholas Tomkinson、Adrian Hall、Kerri Jones、Teyrnon Jones、Niall Killeen、Robert Pörzig、Paul Taylor、Sze Yau

  DOI：10.1055/s-2006-956473

  日期：2006.12

  is described. N-Methyl-O-alkoxyformate hydroxylamine hydrochloride reagents can be prepd. in two high-yielding steps from N-Boc-N-methylhydroxylamine and were found to be bench stable. These were reacted with a variety of carbonyl compds. to give the corresponding α-functionalized products in 48-98% isolated yield via a proposed [3,3]-sigmatropic rearrangement.

  描述了从醛和酮直接形成 α-碳酸酯的第一种方法。可制备N-甲基-O-烷氧基甲酸羟胺盐酸盐试剂。在来自 N-Boc-N-甲基羟胺的两个高产率步骤中，并被发现是稳定的。这些与各种羰基化合物反应。通过建议的 [3,3]-sigmatropic 重排，以 48-98% 的分离产率得到相应的 α-官能化产物。