2-(4-methoxyphenyl)-3-phenyl-4H-chromen-4-one | 130378-66-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 2-(4-methoxyphenyl)-3-phenyl-4H-chromen-4-one
• 英文别名: 2-(4-Methoxyphenyl)-3-phenylchromen-4-one
• CAS: 130378-66-4
• 化学式: C₂₂H₁₆O₃
• 分子量: 328.367
• InChiKey: IXGGQJLZKDGDDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  2-(4-methoxyphenyl)-3-phenyl-4H-chromen-4-one 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 32.25h， 生成 2-[4-(2-pyrrolidinoethoxy)phenyl]-3-phenyl-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. Studies on 2,3-diaryl-1-benzopyrans

  摘要：

  A series of 2,3-diaryl-1-benzopyran analogues substituted at position 4 of 2-phenyl with a hydroxy or pyrrolidinoethoxy residue were synthesized as models for (E)-triarylpropenones constrained in the s-trans conformation. The prototypes, belonging to five chemical series, were evaluated for their estrogen receptor affinity and for estrogen agonist-antagonist activities. The 4H-1-benzopyran-4-one, the 2,3-dihydro-4H-1-benzopyran-4-one, the 4H-1-benzopyran, and the 2,3-dihydro-1-benzopyran derivatives were found to be inactive or only marginally activate as receptor ligands or estrogen agonists-antagonists. In the 2H-1-benzopyran category the parent phenol was also inactive whereas the basic ethers 16 and 26 were modest receptor ligands while being quite active as antiestrogens. In a comparative study the benzopyran 16 was found to be more effective antiestrogen than tamoxifen while being as effective as LY-117018. The benzopyrans have thus emerged as a new class of potent antiestrogens.

  DOI：

  10.1021/jm00174a018
• 作为产物：
  描述：

  1-(2-羟基苯基)-2-苯基乙酮 在 吡啶 、 sodium hydroxide 作用下， 反应 50.25h， 生成 2-(4-methoxyphenyl)-3-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. Studies on 2,3-diaryl-1-benzopyrans

  摘要：

  A series of 2,3-diaryl-1-benzopyran analogues substituted at position 4 of 2-phenyl with a hydroxy or pyrrolidinoethoxy residue were synthesized as models for (E)-triarylpropenones constrained in the s-trans conformation. The prototypes, belonging to five chemical series, were evaluated for their estrogen receptor affinity and for estrogen agonist-antagonist activities. The 4H-1-benzopyran-4-one, the 2,3-dihydro-4H-1-benzopyran-4-one, the 4H-1-benzopyran, and the 2,3-dihydro-1-benzopyran derivatives were found to be inactive or only marginally activate as receptor ligands or estrogen agonists-antagonists. In the 2H-1-benzopyran category the parent phenol was also inactive whereas the basic ethers 16 and 26 were modest receptor ligands while being quite active as antiestrogens. In a comparative study the benzopyran 16 was found to be more effective antiestrogen than tamoxifen while being as effective as LY-117018. The benzopyrans have thus emerged as a new class of potent antiestrogens.

  DOI：

  10.1021/jm00174a018

文献信息

• A facile approach for the synthesis of novel 1-oxa- and 1-aza-flavonyl-4-methyl-1H-benzo[d][1,3]oxazin-2(4H)-ones by microwave enhanced Suzuki–Miyaura coupling using bidentate chromen-4-one-based Pd(<scp>ii</scp>)–diimine complex as catalyst
  作者：Sumit Kumar、Naseem Ahmed

  DOI：10.1039/c5ra15274g

  日期：——

  to diversely substituted 1-oxa- and 1-aza-flavonyl-4-methyl-1H-benzo[d][1,3]oxazin-2(4H)-ones using the microwave assisted phosphine-free Suzuki coupling of bromo flavones with boronic acids using a chromen-4-one-containing Pd(II)–diimine complex (C) as catalyst under aerobic conditions is reported. A small amount of the catalyst (0.3 mol%) was found to be highly effective for coupling to form the products

  使用微波辅助的无膦Suzuki轻松获得不同取代的1-oxa-和1-aza-flavonyl-4-methyl-1 H -benzo [ d ] [1,3] oxazin-2（4 H）-ones溴黄酮与含硼酸的硼酸的耦合使用含铬4的Pd（II）-二亚胺络合物（C据报道在有氧条件下作为催化剂。发现少量的催化剂（0.3摩尔％）对于在温和的反应条件下以18-20分钟的非常高的收率偶合形成产物非常有效。该催化体系与广泛范围的烯烃或芳基溴化物以及芳基或杂芳基硼酸兼容。在筛选了各种催化条件后，发现双齿席夫碱配体的Pd络合物能够有效催化这些反应，产率高达95％。还描述了溶剂，碱和催化剂负载量对偶联反应的影响。
• Palladium-Catalyzed Carbonylative Synthesis of 2,3-Disubstituted Chromones
  作者：Chaoren Shen、Wanfang Li、Hongfei Yin、Anke Spannenberg、Troels Skrydstrup、Xiao-Feng Wu

  DOI：10.1002/adsc.201500858

  日期：2016.2.4

  An unexpected palladium‐catalyzed carbonylative synthesis of 2,3‐disubstituted chromones has been developed. Starting from 2‐bromofluorobenzenes and ketones, the corresponding chromones were produced in good yields. By control experiments, this transformation was found to proceed through a sequential carbonylation/Claisen–Hasse rearrangement/intramolecular nucleophilic aromatic substitution approach

  已经开发出了出乎意料的钯催化的2,3-二取代色酮的羰基合成。从2-溴氟苯和酮开始，以高收率生产了相应的色酮。由对照实验中，这种转变被发现通过连续的羰基化/克莱森-哈斯重排/分子内的亲核芳香取代的方法（S进行Ñ AR）。更具体地说，反应顺序始于酮与邻溴氟苯的钯催化羰基化反应，得到乙烯基苯甲酸酯，随后通过克莱森-哈斯重排将其转化为1,3-二酮。最终产物的分子内年代后产生Ñ的氩反应原位形成1,3-二酮。
• Chroman‐4‐one‐Based Amino Bidentate Ligand: An Efficient Ligand for Suzuki‐Miyaura and Mizoroki‐Heck Coupling Reactions in Aqueous Medium
  作者：Danish Khan、Iram Parveen

  DOI：10.1002/ejoc.202100866

  日期：2021.9.21

  A new family of phosphine-free, air and moisture stable ligand are developed for coupling reaction. The synthesised ligand efficiently catalyzed the coupling reaction with PdCl2. The main advantage of the developed protocol is the tolerance of wide substrate including sterically hindered substrates, low ligand loading and short reaction time with good-to-excellent yield.

  为偶联反应开发了一个新的不含膦、空气和水分稳定的配体系列。合成的配体有效地催化了与 PdCl 2的偶联反应。所开发的协议的主要优点是对宽底物的耐受性，包括空间位阻底物、低配体负载和短反应时间，产率良好。
• SAEED, A.;SHARMA, A. P.;DURANI, N., J. MED. CHEM., 33,(1990) N2, C. 3210-3216
  作者：SAEED, A.、SHARMA, A. P.、DURANI, N.

  DOI：——

  日期：——