4-(4-甲氧基苯基)-4-甲基-2-苯基-1,3-恶唑-5(4H)-酮 | 545377-43-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 4-(4-甲氧基苯基)-4-甲基-2-苯基-1,3-恶唑-5(4H)-酮
• 英文名称: 4-methyl-4-(4-methoxyphenyl)-2-phenyl-4H-oxazol-5-one
• 英文别名: 4-(4-methoxyphenyl)-4-methyl-2-phenyloxazol-5(4H)-one；4-(4-Methoxyphenyl)-4-methyl-2-phenyl-1,3-oxazol-5(4H)-one；4-(4-methoxyphenyl)-4-methyl-2-phenyl-1,3-oxazol-5-one
• CAS: 545377-43-3
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: OESNEEHCBCCEGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基-2-苯基-2-噁唑啉-5-酮 、 Bromo-bis(4-methoxyphenyl)-lambda3-iodane 在 silver carbonate 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 5.0h， 以80%的产率得到4-(4-甲氧基苯基)-4-甲基-2-苯基-1,3-恶唑-5(4H)-酮
  参考文献：
  名称：

  使用溴化芳基碘鎓和碳酸银对内酯进行芳基化：容易获得α-四取代的氨基酸衍生物

  摘要：

  AbstractWith the combined use of silver carbonate, diaryliodonium bromides were successfully utilized as aryl source to realize the highly efficient arylation of azlactones under mild conditions. The reaction worked well with various alkyl‐ and aryl‐substituted azlactones, providing a range of α‐tetrasubstituted amino acid derivatives in moderate to high yields.magnified image

  DOI：

  10.1002/adsc.201400035

文献信息

• Palladium-Catalyzed α-Arylation of Azlactones to Form Quaternary Amino Acid Derivatives
  作者：Xiaoxiang Liu、John F. Hartwig

  DOI：10.1021/ol034570q

  日期：2003.5.1

  of alpha-aryl-alpha-alkyl amino acid derivatives from alpha-amino acids by the arylation of azlactone derivatives is reported. Arylation of azlactones derived from alanine, valine, phenalanine, phenyl glycine, and leucine all provided good yields of the arylated product. Mechanistic studies of this reaction revealed that a stable complex containing a ligand formed by reaction of dba with the azlactone

  [反应：见正文]据报道，通过氮杂内酯衍生物的芳基化反应，由α-氨基酸合成α-芳基-α-烷基氨基酸衍生物。衍生自丙氨酸，缬氨酸，苯丙氨酸，苯基甘氨酸和亮氨酸的内酯的酰化作用均提供了良好的芳基化产物收率。此反应的机理研究表明，当与Pd（dba）（2）引发反应时，含有由dba与氮杂内酯反应形成的配体的稳定络合物说明了dba的新抑制作用。
• Arylation of Azlactones using Diaryliodonium Bromides and Silver Carbonate: Facile Access to α-Tetrasubstituted Amino Acid Derivatives
  作者：Zhuo Chai、Biao Wang、Jia-Nan Chen、Gaosheng Yang

  DOI：10.1002/adsc.201400035

  日期：2014.8.11

  AbstractWith the combined use of silver carbonate, diaryliodonium bromides were successfully utilized as aryl source to realize the highly efficient arylation of azlactones under mild conditions. The reaction worked well with various alkyl‐ and aryl‐substituted azlactones, providing a range of α‐tetrasubstituted amino acid derivatives in moderate to high yields.magnified image