5H-2-(3-chloro-5-methylphenyl)-5-methyloxazol-4-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5H-2-(3-chloro-5-methylphenyl)-5-methyloxazol-4-one
• 英文别名: 2-(3-Chloro-5-methylphenyl)-5-methyl-1,3-oxazol-4-one；2-(3-chloro-5-methylphenyl)-5-methyl-1,3-oxazol-4-one
• 化学式: C₁₁H₁₀ClNO₂
• 分子量: 223.659
• InChiKey: GRTMQFMGVTUWOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-环己基丙-2-烯-1-酮 、 5H-2-(3-chloro-5-methylphenyl)-5-methyloxazol-4-one 在 (S)-bis[3,5-bis(3,5-bis(trifluoromethyl)phenyl)phenyl](3,3-dimethyl-1,5,7-triazabicyclo-[4.3.0]-non-5-ene-8-yl)methanol 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以88%的产率得到(R)-5H-2-(3-chloro-5-methylphenyl)-5-(3-cyclohexyl-3-oxopropyl)-5-methyloxazol-4-one
  参考文献：
  名称：

  1,4-addition reaction of 5H-oxazol-4-ones to vinyl ketones catalyzed by chiral guanidines

  摘要：

  In this Letter, a chiral guanidine-catalyzed 1,4-addition reaction of 5H-oxazol-4-ones to vinyl ketones is described. The 1,4-addition reaction proceeded with a high enantioselectivity using 5H-oxazol-4-ones, substituted with a 3-chloro-5-methylphenyl group, as pronucleophiles and a newly developed chiral guanidine as a catalyst. The optimized reaction conditions were also effective in achieving excellent enantioselectivity in the 1,6-addition to dienones. Subsequent solvolysis of the 1,4-addition adduct yielded the corresponding alpha-hydroxy-5-oxocarboxylates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.11.079

文献信息

• 1,4-addition reaction of 5H-oxazol-4-ones to vinyl ketones catalyzed by chiral guanidines
  作者：Akane Morita、Tomonori Misaki、Takashi Sugimura

  DOI：10.1016/j.tetlet.2014.11.079

  日期：2015.1

  In this Letter, a chiral guanidine-catalyzed 1,4-addition reaction of 5H-oxazol-4-ones to vinyl ketones is described. The 1,4-addition reaction proceeded with a high enantioselectivity using 5H-oxazol-4-ones, substituted with a 3-chloro-5-methylphenyl group, as pronucleophiles and a newly developed chiral guanidine as a catalyst. The optimized reaction conditions were also effective in achieving excellent enantioselectivity in the 1,6-addition to dienones. Subsequent solvolysis of the 1,4-addition adduct yielded the corresponding alpha-hydroxy-5-oxocarboxylates. (C) 2014 Elsevier Ltd. All rights reserved.