4,5-diphenyl-6-(4-methoxyphenyl)-2-pyrone | 65714-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,5-diphenyl-6-(4-methoxyphenyl)-2-pyrone
• 英文别名: 4,5-Diphenyl-6-<4-methoxy-phenyl>-2-pyron；6-(4-methoxy-phenyl)-4,5-diphenyl-pyran-2-one；6-(4-Methoxy-phenyl)-4,5-diphenyl-pyran-2-on；6-(4-Methoxyphenyl)-4,5-diphenylpyran-2-one
• CAS: 65714-05-8
• 化学式: C₂₄H₁₈O₃
• 分子量: 354.405
• InChiKey: MXRIRHIXZUYMBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  200 °C
• 沸点：
  548.6±50.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-diphenyl-6-(4-methoxyphenyl)-2-pyrone 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以2.2 g的产率得到5-oxo-5-(4-methoxyphenyl)-3,4-diphenylpent-3-enoic acid
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. A study using triarylbutenone, benzofuran, and triarylfuran analogs as models for triarylethylenes and triarylpropenones

  摘要：

  In a study of the structure-activity relationship (SAR) of antiestrogens use has been made of certain 1,2,3-triarylbutenones, of 2-arylbenzofurans carrying aryl or aroyl substituents at C3, and of 2,3,4-triarylfurans as conformationally constrained models for triarylethylene (TAE) and triarylpropenone (TAP) prototypes. The position-specific contributions of substituents to receptor affinity and to agonist-antagonist profiles were used as aids in characterizing the relative binding orientation of the prototypes. Although most compounds were found to be weak receptor ligands and poorly active in vivo, the following conclusions could be drawn about their SAR: (i) (Z)-TAPs and TAEs interact with the receptor in an analogous manner using the trans-stilbene core, with their agonist-antagonist profiles depending on the nature of other substructures. (ii) Incorporation into the benzofuran framework introduces a stereoelectronic constraint that compromises the normal binding interactions of TAE, as well as TAP, prototypes, resulting in their poor affinities and weak biological activities. (iii) (E)-TAPs can interact with the receptor through their S-cis conformation, but such a binding mode is unlikely to account for their behavior as antagonists.

  DOI：

  10.1021/jm00128a006
• 作为产物：
  描述：

  4-甲氧基-2-苯基苯乙酮 、 苯丙炔酸甲酯 在 sodium methylate 作用下， 以 乙醚 为溶剂， 反应 48.0h， 以6.4 g的产率得到4,5-diphenyl-6-(4-methoxyphenyl)-2-pyrone
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. A study using triarylbutenone, benzofuran, and triarylfuran analogs as models for triarylethylenes and triarylpropenones

  摘要：

  In a study of the structure-activity relationship (SAR) of antiestrogens use has been made of certain 1,2,3-triarylbutenones, of 2-arylbenzofurans carrying aryl or aroyl substituents at C3, and of 2,3,4-triarylfurans as conformationally constrained models for triarylethylene (TAE) and triarylpropenone (TAP) prototypes. The position-specific contributions of substituents to receptor affinity and to agonist-antagonist profiles were used as aids in characterizing the relative binding orientation of the prototypes. Although most compounds were found to be weak receptor ligands and poorly active in vivo, the following conclusions could be drawn about their SAR: (i) (Z)-TAPs and TAEs interact with the receptor in an analogous manner using the trans-stilbene core, with their agonist-antagonist profiles depending on the nature of other substructures. (ii) Incorporation into the benzofuran framework introduces a stereoelectronic constraint that compromises the normal binding interactions of TAE, as well as TAP, prototypes, resulting in their poor affinities and weak biological activities. (iii) (E)-TAPs can interact with the receptor through their S-cis conformation, but such a binding mode is unlikely to account for their behavior as antagonists.

  DOI：

  10.1021/jm00128a006

文献信息

• Pyrone series. Part II. 4: 5: 6-Triaryl-2-pyrones
  作者：Gabra Soliman、Ibrahim El-Sayed El-Kholy

  DOI：10.1039/jr9550002911

  日期：——
• DURANI, NEELAM;JAIN, RAKA;SAEED, ASHRAF;DIKSHIT, DINESH K.;DURANI, SUSHEE+, J. MED. CHEM., 32,(1989) N, C. 1700-1707
  作者：DURANI, NEELAM、JAIN, RAKA、SAEED, ASHRAF、DIKSHIT, DINESH K.、DURANI, SUSHEE+

  DOI：——

  日期：——
• EL-KHOLY I. E.; MISHRIKEY M. M.; FUID-ALLA H. M., J. HETEROCYCL. CHEM. <JHTC-AD>, 1977, 14, NO 5, 845-852
  作者：EL-KHOLY I. E.、 MISHRIKEY M. M.、 FUID-ALLA H. M.

  DOI：——

  日期：——