(E)-3-(2-(3-oxocyclohexyl)vinyl)oxazolidin-2-one | 1173276-74-8

• 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: (E)-3-(2-(3-oxocyclohexyl)vinyl)oxazolidin-2-one
• 英文别名: 3-[(E)-2-(3-oxocyclohexyl)ethenyl]-1,3-oxazolidin-2-one
• CAS: 1173276-74-8
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: CJAXECPLOYFCIA-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-(3-oxocyclohexyl)vinyl)oxazolidin-2-one 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到3-oxocyclohexanecarbaldehyde
  参考文献：
  名称：

  Cyclization Reactions through DDQ-Mediated Vinyl Oxazolidinone Oxidation

  摘要：

  Vinyl oxazolidinones react with DDQ to form alpha,beta-unsaturated acyliminium ions in a new method for forming electrophiles under oxidative conditions. Appended nucleophiles undergo 1,4-addition reactions with these intermediates to form cyclic vinyl oxazolidinones with good levels of diastereocontrol, highlighting a new approach to utilizing oxidative carbon-hydrogen bond functionalization to increase molecular complexity.

  DOI：

  10.1021/ol901188q
• 作为产物：
  描述：

  (E)-8-(2-oxooxazolidin-3-yl)octa-1,7-dien-2-yl acetate 在 2,6-二氯吡啶 、 lithium perchlorate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以76%的产率得到(E)-3-(2-(3-oxocyclohexyl)vinyl)oxazolidin-2-one
  参考文献：
  名称：

  Cyclization Reactions through DDQ-Mediated Vinyl Oxazolidinone Oxidation

  摘要：

  Vinyl oxazolidinones react with DDQ to form alpha,beta-unsaturated acyliminium ions in a new method for forming electrophiles under oxidative conditions. Appended nucleophiles undergo 1,4-addition reactions with these intermediates to form cyclic vinyl oxazolidinones with good levels of diastereocontrol, highlighting a new approach to utilizing oxidative carbon-hydrogen bond functionalization to increase molecular complexity.

  DOI：

  10.1021/ol901188q

文献信息

• Cyclization Reactions through DDQ-Mediated Vinyl Oxazolidinone Oxidation
  作者：Lei Liu、Paul E. Floreancig

  DOI：10.1021/ol901188q

  日期：2009.7.16

  Vinyl oxazolidinones react with DDQ to form alpha,beta-unsaturated acyliminium ions in a new method for forming electrophiles under oxidative conditions. Appended nucleophiles undergo 1,4-addition reactions with these intermediates to form cyclic vinyl oxazolidinones with good levels of diastereocontrol, highlighting a new approach to utilizing oxidative carbon-hydrogen bond functionalization to increase molecular complexity.