4,4-Diphenyl-but-3-enoic acid 6-oxo-3,3-diphenyl-3,6-dihydro-2H-pyran-2-yl ester | 138430-07-6

• 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: 4,4-Diphenyl-but-3-enoic acid 6-oxo-3,3-diphenyl-3,6-dihydro-2H-pyran-2-yl ester
• CAS: 138430-07-6
• 化学式: C₃₃H₂₆O₄
• 分子量: 486.567
• InChiKey: FHNQPEJHMLEBFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-hydroxy-4,4-diphenylcyclohexa-2,5-dien-1-one 在 rose bengal 四甲基氟化铵 、 氧气 作用下， 以 氯仿 为溶剂， 反应 9.5h， 以32%的产率得到4,4-Diphenyl-but-3-enoic acid 6-oxo-3,3-diphenyl-3,6-dihydro-2H-pyran-2-yl ester
  参考文献：
  名称：

  The photosensitized oxidation of α-keto enols: A singlet oxygen approach to 2-oxasteroids

  摘要：

  Fluoride ion catalyzed photosensitized singlet oxygenation of 2-hydroxycyclohexa-2,5-dien-1-ones 15a and b and the related steroidal alpha-keto enols 18a-g, generated the cyclohexenone lactols 16a-b and the corresponding steroidal analogs 19a-g generally in moderate to good yields (60-75%). Since the lactols can be conveniently reduced to the desired 2-oxasteroids in high yields, this 1O2 route presents itself as a synthetically acceptable alternative to the previously reported BCA approach3a for the preparation of 2-oxasteroids, especially in the case of base sensitive compounds.

  DOI：

  10.1016/s0040-4020(01)96177-0

文献信息

• The photosensitized oxidation of α-keto enols: A singlet oxygen approach to 2-oxasteroids
  作者：Aryeh A. Frimer、Shlomo Ripstos、Vered Marks、Gladis Aljadeff、Judith Hameiri-Buch、Pessia Gilinsky-Sharon

  DOI：10.1016/s0040-4020(01)96177-0

  日期：1991.9

  Fluoride ion catalyzed photosensitized singlet oxygenation of 2-hydroxycyclohexa-2,5-dien-1-ones 15a and b and the related steroidal alpha-keto enols 18a-g, generated the cyclohexenone lactols 16a-b and the corresponding steroidal analogs 19a-g generally in moderate to good yields (60-75%). Since the lactols can be conveniently reduced to the desired 2-oxasteroids in high yields, this 1O2 route presents itself as a synthetically acceptable alternative to the previously reported BCA approach3a for the preparation of 2-oxasteroids, especially in the case of base sensitive compounds.