phenyl(2,5,6,6-tetraphenyl-6H-[1,4]oxazin-3-yl)methanone | 1341189-57-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: phenyl(2,5,6,6-tetraphenyl-6H-[1,4]oxazin-3-yl)methanone
• 英文别名: Phenyl-(2,5,6,6-tetraphenyl-1,4-oxazin-3-yl)methanone
• CAS: 1341189-57-8
• 化学式: C₃₅H₂₅NO₂
• 分子量: 491.589
• InChiKey: SCPWWPJRUWGXCO-UHFFFAOYSA-N

物化性质

• 沸点：
  628.3±55.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2,3-triphenyl-2H-azirine 、 (1Z)-2-偶氮基-3-氧代-1,3-二苯基-1-丙烯-1-醇 以 甲苯 为溶剂， 反应 2.0h， 以6%的产率得到phenyl(2,5,6,6-tetraphenyl-6H-[1,4]oxazin-3-yl)methanone
  参考文献：
  名称：

  Nonconcerted Cycloaddition of 2H-Azirines to Acylketenes: A Route to N-Bridgehead Heterocycles

  摘要：

  Reactions of acylketenes, generated from diazo diketones, with 2-unsubstituted and 2-monosubstituted 3-aryl-2H-azirines lead to 1:1 or 2:1 adducts, which are derivatives of 5-oxa-1-azabicyclo[4.1.0]hept-3-ene or 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene. According to DFT B3LYP/6-31G(d) computations, the formation of (4+2)-monoadducts proceeds via a stepwise non-pericyclic mechanism. Reaction with methanol transforms quantitatively both 1:1 and 2:1 adducts into 1,4-oxazepine derivatives.

  DOI：

  10.1021/jo201563b

文献信息

• Nonconcerted Cycloaddition of 2<i>H</i>-Azirines to Acylketenes: A Route to N-Bridgehead Heterocycles
  作者：Alexander F. Khlebnikov、Mikhail S. Novikov、Viktoriia V. Pakalnis、Dmitry S. Yufit

  DOI：10.1021/jo201563b

  日期：2011.11.18

  Reactions of acylketenes, generated from diazo diketones, with 2-unsubstituted and 2-monosubstituted 3-aryl-2H-azirines lead to 1:1 or 2:1 adducts, which are derivatives of 5-oxa-1-azabicyclo[4.1.0]hept-3-ene or 5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene. According to DFT B3LYP/6-31G(d) computations, the formation of (4+2)-monoadducts proceeds via a stepwise non-pericyclic mechanism. Reaction with methanol transforms quantitatively both 1:1 and 2:1 adducts into 1,4-oxazepine derivatives.