(E)-3-([1,1'-biphenyl]-4-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one | 41255-15-6

• 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: (E)-3-([1,1'-biphenyl]-4-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• 英文别名: (E)-1-(2-hydroxyphenyl)-3-(4-phenylphenyl)prop-2-en-1-one
• CAS: 41255-15-6
• 化学式: C₂₁H₁₆O₂
• 分子量: 300.357
• InChiKey: OPPYKLKRHFXOKU-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  4
• 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
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-([1,1'-biphenyl]-4-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one 在 sodium tetrahydroborate 、 磷酸 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 54.5h， 生成 4-hydroxy-3-[2-(4-phenylphenyl)-3,4-dihydro-2H-chromen-4-yl]chromen-2-one
  参考文献：
  名称：

  Design and synthesis of novel diphenacoum-derived, conformation-restricted vitamin K 2,3-epoxide reductase inhibitors

  摘要：

  Two novel diphenacoum-derived analogues 5 and 6 are designed, synthesized and tested as potential vitamin K 2,3-epoxide reductase (VKOR) inhibitors. The inhibition studies indicated that 5 is a potent VKOR inhibitor, which confirmed that the replacement of the tetrahydronaphthalene on diphenacoum to a chroman functionality does not have a major impact on inhibition potency. The conformation-restricted compound 6 is a moderate inhibitor which may serve as a lead compound for further study of the mode of action of coumarin-type anticoagulants at the molecular level. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.005
• 作为产物：
  描述：

  N,N-二乙基水杨酰胺 在 lithium diisopropyl amide 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 反应 41.17h， 生成 (E)-3-([1,1'-biphenyl]-4-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  从氨基甲酸酯到查尔酮：连续的阴离子炸薯条重排，阴离子Si→C烷基重排和Claisen–Schmidt缩合

  摘要：

  开发了一种高效的一锅法，可从苯基二乙基氨基甲酸酯合成各种2'-羟基查耳酮，其特征是连续进行一次Snieckus-Fries重排，阴离子Si→C烷基重排和Claisen-Schmidt缩合。该协议的适用性通过高效合成抗炎天然产物长果皮苷得到了证明。还提供了机制的见解。

  DOI：

  10.1021/acs.orglett.8b02269

文献信息

• Extended Aromatic and Heteroaromatic Ring Systems in the Chalcone–Flavanone Molecular Switch Scaffold
  作者：Brian M. Muller、Theodore J. Litberg、Reid A. Yocum、Chanté A. Pniewski、Marc J. Adler

  DOI：10.1021/acs.joc.6b00986

  日期：2016.7.1

  substitutions alter the pH range in which rapid interconversion occurs. Herein, more impactful structural modifications were performed via alteration of the characteristic phenyl rings to alternative aromatic systems. It was determined that the scaffold was still viable after these changes and that the range of accessible midpoint pH values was markedly increased. To further explore the switch’s scope, scaffolds

  以前对邻羟基查耳酮/黄酮酮分子转换支架的研究表明，简单的取代改变了发生快速相互转化的pH范围。本文中，通过将特征性苯环改变为替代的芳族体系进行了更具影响力的结构修饰。确定在这些改变之后，支架仍然是可行的，并且可达到的中点pH值的范围显着增加。为了进一步探索开关的范围，还研究了能够发生多个开关事件的支架。
• The Direct Preparation of Flavones from 2′-Hydroxychalcones Using Disulfides
  作者：Yukio Hoshino、Toshinori Oohinata、Noboru Takeno

  DOI：10.1246/bcsj.59.2351

  日期：1986.7

  Flavone was obtained by a reaction of 2′-hydroxychalcone with disulfides in good yield. Among several disulfides, diphenyl disulfide gave the best result. Under the same conditions, some flavones were obtained from the corresponding 2′-hydroxychalcones in satisfactory yields.

  黄酮是通过 2'-羟基查尔酮与二硫化物以良好的收率反应获得的。在几种二硫化物中，二苯基二硫化物的效果最好。在相同条件下，从相应的 2'-羟基查耳酮中以令人满意的收率获得了一些黄酮。
• Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride
  作者：Motofumi Miura、Karin Shigematsu、Masaharu Toriyama、Shigeyasu Motohashi

  DOI：10.1016/j.tetlet.2021.153480

  日期：2021.11

  flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

  在温和条件下，从相应的羟基查耳酮与催化量的氟化铯水溶液通过氧杂-迈克尔加成容易合成总共 36 种黄烷酮，其中包括多环芳环和杂环。该方法可用于作为 SARS-CoV-2 刺突蛋白的已知强效抑制剂圣草酚的可扩展合成。
• Coumarin based novel ligands in the Suzuki–Miyaura and Mizoroki–Heck cross-couplings under aqueous medium
  作者：Mohammed Waheed、Naseem Ahmed

  DOI：10.1016/j.tetlet.2016.07.028

  日期：2016.8

  Coumarin-based novel ligands (benzylidine-bis-(4-hydroxycoumarin)-diethylamines) were easily synthesized using 4-hydroxycoumarin, aromatic aldehydes, and diethylamine. The ionic ligand structure was established by X-ray study. They are air and moisture stable ligands and have shown highly efficient catalytic activity with Pd(OAc)2 (0.1 mol % loading) in the Suzuki–Miyaura and (0.3 mol % loading) in

  使用4-羟基香豆素，芳族醛和二乙胺可以轻松合成基于香豆素的新型配体（苄基双（4-羟基香豆素）-二乙胺）。通过X射线研究建立了离子配体结构。它们是空气和湿气稳定的配体，在铃木-Miyaura中的Pd（OAc）2（0.1 mol％负载）和Mizoroki-Heck交叉偶合反应中的Pd（OAc）2（在水中或0.3 mol％负载）中显示出高效的催化活性水/乙醇混合物。钯催化剂可以有效地重复使用，而不会影响反应中各种官能团。
• Inhibitory activity of prostaglandin E2 production by the synthetic 2′-hydroxychalcone analogues: Synthesis and SAR study
  作者：Thanh-Dao Tran、Haeil Park、Hyun Pyo Kim、Gerhard F. Ecker、Khac-Minh Thai

  DOI：10.1016/j.bmcl.2009.02.001

  日期：2009.3

  A series of 2'-hydroxychalcones has been synthesized and screened for their in vitro inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells. Structure-activity relationship study suggested that inhibitory activity against prostaglandin E-2 production was governed to a greater extent by the substituent on B ring of the chalcone, and most of the active compounds have at least two methoxy or benzyloxy groups on B ring. The relationship between chalcone structures and their PGE(2) inhibitory activities was also interpreted by docking study on cyclooxygenase-2. (C) 2009 Elsevier Ltd. All rights reserved.