trans-7-hydroxy-2,3-diphenyl-2,3-dihydro-4H-1-benzopyran-4-one | 18435-79-5

• 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: trans-7-hydroxy-2,3-diphenyl-2,3-dihydro-4H-1-benzopyran-4-one
• 英文别名: trans-2,3-Diphenyl-7-hydroxy-chromanon-4；(2R,3S)-7-hydroxy-2,3-diphenyl-2,3-dihydrochromen-4-one
• CAS: 18435-79-5
• 化学式: C₂₁H₁₆O₃
• 分子量: 316.356
• InChiKey: DLLDNPGPBGBEDI-CTNGQTDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-<2-hydroxy-4-<(tetrahydropyran-2-yl)oxy>phenyl>-2-phenylethanone 在 哌啶 、 水 作用下， 以 溶剂黄146 、 异丙醇 为溶剂， 反应 90.0h， 生成 trans-7-hydroxy-2,3-diphenyl-2,3-dihydro-4H-1-benzopyran-4-one
  参考文献：
  名称：

  An Efficient Process for the Synthesis of trans-2,3-Disubstituted-2,3-dihydro-4H-1-benzopyran-4-ones (Chroman-4-ones)

  摘要：

  The piperidine catalyzed Knoevenagel condensation of 2'-aryl/alkyl-2-hydroxyacetophenones 7 and aryl/alkylaldehydes 8 in refluxing isopropyl alcohol with azeotropic removal of water affords, in high yield, equilibrium mixtures of E- and Z-chalcones 9 and cis- and trans-chroman-4-ones 10 which are effectively isomerized in situ to the trans-2,3-diaryl/alkylchroman-4-ones, following the addition of 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) to the cooled reaction mixture and may be isolated in high purities (91-99%) by simple filtration, with good to excellent yields (70-95%). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00101-0

文献信息

• An Efficient Process for the Synthesis of trans-2,3-Disubstituted-2,3-dihydro-4H-1-benzopyran-4-ones (Chroman-4-ones)
  作者：Richard W. Draper、Bin Hu、Radha V. Iyer、Xun Li、Yuelie Lu、Mohammad Rahman、Eugene J. Vater

  DOI：10.1016/s0040-4020(00)00101-0

  日期：2000.3

  The piperidine catalyzed Knoevenagel condensation of 2'-aryl/alkyl-2-hydroxyacetophenones 7 and aryl/alkylaldehydes 8 in refluxing isopropyl alcohol with azeotropic removal of water affords, in high yield, equilibrium mixtures of E- and Z-chalcones 9 and cis- and trans-chroman-4-ones 10 which are effectively isomerized in situ to the trans-2,3-diaryl/alkylchroman-4-ones, following the addition of 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) to the cooled reaction mixture and may be isolated in high purities (91-99%) by simple filtration, with good to excellent yields (70-95%). (C) 2000 Elsevier Science Ltd. All rights reserved.