3-([1,1'-biphenyl]-4-yl)-1-(4-methoxyphenyl)prop-2-en-1-one | 6552-69-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 3-([1,1'-biphenyl]-4-yl)-1-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 1-<4-Methoxy-phenyl>-3-biphenyl-(4)-yl-propen-(2)-on-(1)；p-Anisyl-β-(p-biphenylyl)-vinyl-keton；3-Biphenyl-4-yl-1-(4-methoxy-phenyl)-propenon；1-Biphenylyl-(4)-3-(4-methoxy-phenyl)-prop-1-en-3-on；2-Propen-1-one, 3-[1,1'-biphenyl]-4-yl-1-(4-methoxyphenyl)-；1-(4-methoxyphenyl)-3-(4-phenylphenyl)prop-2-en-1-one
• CAS: 6552-69-8
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: KMWZUECQAQRWGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对苯基苯甲醛 、 对甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以83%的产率得到3-([1,1'-biphenyl]-4-yl)-1-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis and bioactivity of chalcones and its analogues

  摘要：

  The Vernohia anthelmintica L's extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and a, beta-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a-15a, 20a and 1 b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40 mu g/mL (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.03.018

文献信息

• Oxygen as single oxidant for two steps: base-free one-pot Pd(<scp>ii</scp>)-catalyzed alcohol oxidation &amp; arylation to halogen-intact β-aryl α,β-enones
  作者：Mari Vellakkaran、Murugaiah M. S. Andappan、Kommu Nagaiah

  DOI：10.1039/c4ra07478e

  日期：——

  Using oxygen as the sole oxidant for two steps, we developed a new method to synthesize β-aryl α,β-enones by fine-tuning the Pd(ii)-catalyzed oxidation of allyl alcohol to subsequent arylation with arylboronic acids, arylboronic ester and aryltrifluoroborate salt.

  使用氧气作为唯一氧化剂的两步法，我们开发了一种新方法，通过微调Pd（II）催化的烯丙醇氧化反应，然后与芳基硼酸、芳基硼酯和芳基三氟硼酸盐进行芳基化反应，合成β-芳基α，β-烯酮。
• CN116162027
  申请人：——

  公开号：——

  公开（公告）日：——