1a,7a-Dihydro-1a-(4-methylphenyl)-7H-oxireno<1>benzopyran-7-one | 134051-31-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 1a,7a-Dihydro-1a-(4-methylphenyl)-7H-oxireno<1>benzopyran-7-one
• 英文别名: 1a-(4-Methylphenyl)-1a,7a-dihydro-7H-oxireno[2,3-b]chromen-7-one；1a-(4-methylphenyl)-7aH-oxireno[2,3-b]chromen-7-one
• CAS: 134051-31-3
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: JJLSBOMQISREHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1a,7a-Dihydro-1a-(4-methylphenyl)-7H-oxireno<1>benzopyran-7-one 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以100%的产率得到3-羟基-4'-甲基黄酮
  参考文献：
  名称：

  Epoxidation of flavones by dimethyldioxirane

  摘要：

  The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported. These labile epoxides were isolated and completely characterized by UV, IR, H-1 and C-13 NMR, MS, and C, H analyses. Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n. Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f as a mixture of cis and trans isomers.

  DOI：

  10.1021/jo00026a020
• 作为产物：
  描述：

  2-(4-甲基苯基)-4H-1-苯并吡喃-4-酮 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 23.0h， 以100%的产率得到1a,7a-Dihydro-1a-(4-methylphenyl)-7H-oxireno<1>benzopyran-7-one
  参考文献：
  名称：

  Dimethyldioxirane epoxidation of flavones.

  摘要：

  Various flavones 1 were converted in excellent yields to the hitherto unknown corresponding epoxides 3 by epoxidation with dimethyldioxirane at subambient temperatures.

  DOI：

  10.1016/s0040-4039(00)74482-0

文献信息

• Epoxidation of flavones by dimethyldioxirane
  作者：Waldemar Adam、Dieter Golsch、Lazaros Hadjiarapoglou、Tamas Patonay

  DOI：10.1021/jo00026a020

  日期：1991.12

  The synthesis of epoxides 2 by epoxidation of flavones 1 with isolated dimethyldioxirane (as acetone solution) at subambient temperatures is reported. These labile epoxides were isolated and completely characterized by UV, IR, H-1 and C-13 NMR, MS, and C, H analyses. Warming to room temperature led to rearrangement to afford quantitatively the 3-hydroxyflavones 3b,h,i,n. Treatment of the epoxides 2b,f with methanol led to the 3-hydroxy-2-methoxyflavanones 4b,f as a mixture of cis and trans isomers.
• Dimethyldioxirane epoxidation of flavones.
  作者：Waldemar Adam、Dieter Golsch、Lazaros Hadjiarapoglou、Tamas Patonay

  DOI：10.1016/s0040-4039(00)74482-0

  日期：1991.2

  Various flavones 1 were converted in excellent yields to the hitherto unknown corresponding epoxides 3 by epoxidation with dimethyldioxirane at subambient temperatures.