3-Methyl-4,5-cyclohexyl-4,5-cis-dihydro-4-oxazolin-2-one | 87767-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-Methyl-4,5-cyclohexyl-4,5-cis-dihydro-4-oxazolin-2-one
• 英文别名: 3-methyl-cis-4,5-tetramethylene-2-oxazolidinone；cis-hexahydro-benzoxazol-2-one；(+/-)-3-methyl-(3ar,7ac)-hexahydro-benzoxazol-2-one；(+/-)-3-Methyl-(3ar,7ac)-hexahydro-benzoxazol-2-on；(3aS,7aR)-3-methyl-3a,4,5,6,7,7a-hexahydro-1,3-benzoxazol-2-one
• CAS: 87767-86-0；95891-60-4；122745-25-9
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: IIBRNKYGNWDOKD-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  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

文献信息

• Iminyl, amidyl, and carbamyl radicals from O-benzoyl oximes and O-benzoyl hydroxamic acid derivatives
  作者：Jean Boivin、Anne-Claude Callier-Dublanchet、Béatrice Quiclet-Sire、Anne-Marie Schiano、Samir Z. Zard

  DOI：10.1016/0040-4020(95)00319-4

  日期：1995.6

  Oxime benzoates and O-benzoyl hydroxamic acid derivatives react with tributylstannane in the presence of AIBN to give iminyl, amidyl, and carbamyl radicals which can be captured by an internal olefin.

  肟苯甲酸酯和O-苯甲酰基异羟肟酸衍生物在AIBN存在下与三丁基锡烷反应，生成亚胺基、,基和氨基甲酸酯基团，这些基团可以被内烯烃捕获。
• Processes For Production of Phenolic 4-Biphenylylazetidin-2-Ones
  申请人：Barden Timothy C.

  公开号：US20080200669A1

  公开（公告）日：2008-08-21

  The present invention relates to processes for the production of phenolic 4-biphenylylazetidin-2-one derivatives of formula

  本发明涉及制备式为phenolic 4-biphenylylazetidin-2-one衍生物的工艺。
• Mousseron et al., Bulletin de la Societe Chimique de France, 1953, p. 737,743
  作者：Mousseron et al.

  DOI：——

  日期：——
• Organotelluriums. 20. Aminotellurinylation of olefins and its utilization for synthesis of 2-oxazolidinones
  作者：Nan Xing Hu、Yoshio Aso、Tetsuo Otsubo、Fumio Ogura

  DOI：10.1021/jo00279a031

  日期：1989.9
• Reaction of oximes with dimethyl carbonate: a new entry to 3-methyl-4,5-disubstituted-4-oxazolin-2-ones
  作者：C. A. Marques、M. Selva、P. Tundo、F. Montanari

  DOI：10.1021/jo00073a041

  日期：1993.10

  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.