2-(4-hydroxyphenyl)-1,3-diphenyl-2-propen-1-one | 94369-84-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-(4-hydroxyphenyl)-1,3-diphenyl-2-propen-1-one
• 英文别名: 2-(4-hydroxyphenyl)-1,3-diphenylprop-2-en-1-one
• CAS: 94369-84-3
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: GDSQTRDKUOAIIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N,O-双三甲硅基乙酰胺 、 2-(4-hydroxyphenyl)-1,3-diphenyl-2-propen-1-one 生成 (E)-1,3-Diphenyl-2-(4-trimethylsilanyloxy-phenyl)-propenone
  参考文献：
  名称：

  Fragmentation and rearrangement reactions in certain 1,2,3-triaryl-2-propen-1-ones following electron impact and chemical ionization

  摘要：

  AbstractThe electron impact (EI) and chemical ionization (CI) mass spectra of certain 1,2,3‐triaryl‐2‐propen‐1‐ones (TAPs) have been studied in detail with the help of exact mass measurements, deuterium labelling and metastable data. TheE‐ andZ‐isomeric pairs do not show any difference in their behaviour under EI or CH4CI conditions. EI‐induced rearangement reactions in the TAPs include aryl migration to carbonium ion centres. A study of the metastable transitions reveals aryl group interchange in the molecular ions prior to fragmentation. Under EI conditions loss of arene involves either C(2) or C(3) aryl groups while under CI conditions the C(1) aryl is lost as a neutral arene molecule. Mechanisms for the different fragmentation modes are given.

  DOI：

  10.1002/oms.1210200310
• 作为产物：
  描述：

  4-(2-oxo-2-phenylethyl)phenyl acetate 在 哌啶 、 氢氧化钾 、 溶剂黄146 作用下， 以 乙醇 、 苯 为溶剂， 反应 4.0h， 生成 2-(4-hydroxyphenyl)-1,3-diphenyl-2-propen-1-one
  参考文献：
  名称：

  Structure-activity relationship of estrogens: receptor affinity and estrogen antagonist activity of certain (E)- and (2)-1,2,3-triaryl-2-propen-2-ones

  摘要：

  (E)-和(Z)-1,2,3-三苯甲丙二烯酮及其酚类和醚类的类物在芳香环的para位被取代的情况下被合成了，这些化合物的立体结构是基于它们的光谱数据进行判断的。从雌激素受体亲和力以及雌激素亲和力的协同作用和拮抗作用的层面，探讨了丙三环酮的结构活性关系。无论是(E)-还是(Z)-的丙烯酮都与小鼠子宫细胞受体发生了竞争性的结合，酚类的类物通常比未取代的结构和醚类的丙烯酮有更强的亲和力。可以与雌激素结合的丙烯酮的身影作为新的雌激素受体配体逐渐浮现，但它们与(Z)-同分异构体在结合特异性方面有很大的不同。生胎性以及抑生胎性在幼鼠中的测试显示，虽然有些化合物具有微弱的雌激素性质，但几乎所有的同分异构体丙烯酮都具有一定程度的抑生胎性。

  DOI：

  10.1021/jm00382a019

文献信息

• Structure-activity relationship of estrogens: receptor affinity and estrogen antagonist activity of certain (E)- and (2)-1,2,3-triaryl-2-propen-2-ones
  作者：Shubhra Mittal、Susheel Durani、Randhir S. Kapil

  DOI：10.1021/jm00382a019

  日期：1985.4

  (E)- and (Z)-1,2,3-triphenyl-2-propen-1-ones and some of their phenolic and alkoxy analogues, substituted at the para position in one or more of the aromatic rings, were synthesized and assigned geometry on the basis of their spectroscopic data. The structure-activity relationship of the triarylpropenones was studied from the point of view of their estrogen receptor affinity and estrogen agonist and antagonist activities. (E)- as well as (Z)-propenones were found to compete with estradiol for binding with the mouse uterine cytosol receptors, with phenolic analogues usually more potent than the unsubstituted as well as alkoxypropenones. The (E)-propenones, which have now emerged as a new group of estrogen receptor ligands, were found to differ from Z isomers quite markedly in their binding specificities. The uterotrophic and antiuterotrophic assays in immature mice revealed that while some of the compounds were marginally estrogenic, nearly all the isomeric propenones were antiestrogenic to a varying degree.

  (E)-和(Z)-1,2,3-三苯甲丙二烯酮及其酚类和醚类的类物在芳香环的para位被取代的情况下被合成了，这些化合物的立体结构是基于它们的光谱数据进行判断的。从雌激素受体亲和力以及雌激素亲和力的协同作用和拮抗作用的层面，探讨了丙三环酮的结构活性关系。无论是(E)-还是(Z)-的丙烯酮都与小鼠子宫细胞受体发生了竞争性的结合，酚类的类物通常比未取代的结构和醚类的丙烯酮有更强的亲和力。可以与雌激素结合的丙烯酮的身影作为新的雌激素受体配体逐渐浮现，但它们与(Z)-同分异构体在结合特异性方面有很大的不同。生胎性以及抑生胎性在幼鼠中的测试显示，虽然有些化合物具有微弱的雌激素性质，但几乎所有的同分异构体丙烯酮都具有一定程度的抑生胎性。
• Fragmentation and rearrangement reactions in certain 1,2,3-triaryl-2-propen-1-ones following electron impact and chemical ionization
  作者：K. P. Madhusudanan、Shubhra Mittal、S. Durani、R. S. Kapil

  DOI：10.1002/oms.1210200310

  日期：1985.3

  AbstractThe electron impact (EI) and chemical ionization (CI) mass spectra of certain 1,2,3‐triaryl‐2‐propen‐1‐ones (TAPs) have been studied in detail with the help of exact mass measurements, deuterium labelling and metastable data. TheE‐ andZ‐isomeric pairs do not show any difference in their behaviour under EI or CH4CI conditions. EI‐induced rearangement reactions in the TAPs include aryl migration to carbonium ion centres. A study of the metastable transitions reveals aryl group interchange in the molecular ions prior to fragmentation. Under EI conditions loss of arene involves either C(2) or C(3) aryl groups while under CI conditions the C(1) aryl is lost as a neutral arene molecule. Mechanisms for the different fragmentation modes are given.