1-(4-methoxyphenyl)-2-phenylhexanone | 479498-88-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(4-methoxyphenyl)-2-phenylhexanone
• 英文别名: 1-(4-Methoxyphenyl)-2-phenylhexan-1-one
• CAS: 479498-88-9
• 化学式: C₁₉H₂₂O₂
• 分子量: 282.382
• InChiKey: SSCLXLNUCJTEGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-2-phenylhexanone 在 47percent HBr 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1,1-bis-(4-methoxyphenyl)-2-phenylhex-1-ene
  参考文献：
  名称：

  Investigations on Estrogen Receptor Binding. The Estrogenic, Antiestrogenic, and Cytotoxic Properties of C2-Alkyl-Substituted 1,1-Bis(4-hydroxyphenyl)-2-phenylethenes

  摘要：

  C2-Alkyl-substituted 1,1-bis(4-hydroxyphenyl)-2-phenylethenes were synthesized and assayed for estrogen receptor binding in a competition experiment with radiolabeled estradiol ([H-3]-E-2) using calf uterine cytosol. The relative binding affinity decreased with the length of the side chain R = H (3a: 35.2%) > Me (3b: 32.1%) > Et (3c: 6.20%); CH2CF3 (3d: 5.95%) > n-Pr (3e: 2.09%) > Bu (3f: 0.62%). Agonistic and antagonistic effects were evaluated in the luciferase assay with MCF-7-2a cells stably transfected with the plasmid ERE(wtc)luc. All compounds showed high antiestrogenic activity without significant agonistic potency. The comparison of the IC50 values for the inhibition of E2 (1 nM) documented the dependence of the antagonistic effects on the kind of the side chain: 3a (IC50 = 150 nM), 3b (IC50 = 30 nM), and 3f (IC50 = 500 nM) were weak antagonists, while 3c (IC50 = 15 nM), 3d (IC50 = 9 nM), and 3e (IC50 = 50 nM) were full antiestrogens and antagonized the effect of E2 completely. The most active compound 3d possessed the same antagonistic potency as 4-hydroxytamoxifen (40HT: IC50 = 7 nM) without bearing a basic side chain. 3d as well as all other 1,1-bis(4-hydroxyphenyl)-2-phenylalkenes were not able to influence the proliferation of hormone dependent MCF-7 cells despite the antagonistic mode of action. In this assay tamoxifen (TAM) and 40HT reduced the cell growth concentration dependent up to T/C-corr = 15% and 25%, respectively.

  DOI：

  10.1021/jm0209230
• 作为产物：
  描述：

  1-己炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氯[三(对三氟甲基苯基)膦]金(I) 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 1-(4-methoxyphenyl)-2-phenylhexanone
  参考文献：
  名称：

  不含光敏剂的可见光介导的金催化炔烃的1,2-双官能化

  摘要：

  在可见光照射下，炔烃与芳基重氮盐在甲醇中金催化的炔烃分子间双官能团化反应可提供中等至良好收率的各种α-芳基酮。与先前有关涉及氧化还原循环的金催化反应的报告相比，不需要外部氧化剂或光敏剂。在温和的反应条件下，反应平稳进行，并显示出宽泛的官能团耐受性。该方法的进一步应用证明了乙烯基金中间体芳基化的普遍适用性，而不是通常使用的原型脱金属步骤。通过此步骤，可以轻松地通过一锅法访问功能化产品。使用P，N-双齿配体，获得了稳定的芳基金（III）物种，

  DOI：

  10.1002/anie.201511487