6-methoxy-2-(4-methoxy-phenyl)-3-phenyl-indene | 125791-29-9

• 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: 6-methoxy-2-(4-methoxy-phenyl)-3-phenyl-indene
• 英文别名: 6-methoxy-2-(4-methoxyphenyl)-3-phenyl-1H-indene；6-Methoxy-2-(4-methoxy-phenyl)-3-phenyl-inden
• CAS: 125791-29-9
• 化学式: C₂₃H₂₀O₂
• 分子量: 328.411
• InChiKey: DPJXOCQVFDUIRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-methoxy-2-(4-methoxy-phenyl)-3-phenyl-indene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-Hydroxy-phenyl)-1-phenyl-3H-inden-5-ol
  参考文献：
  名称：

  Differential Response of Estrogen Receptor Subtypes to 1,3-Diarylindene and 2,3-Diarylindene Ligands

  摘要：

  Estrogen receptors (ERs) control transcription of genes important for normal human development and reproduction. The signaling networks are complex, and there is a need for a molecular level understanding of the roles of receptor subtypes ER alpha and ER beta in normal physiology and as therapeutic targets. We synthesized two series of ER ligands, based on a common indene scaffold, in an attempt to develop compounds that can selectively modulate ER-mediated transcription. The 3-ethyl-1,2-diarylindenes, utilizing an amide linker for the 1-aryl extension, bind weakly to the ERs. The 2,3-diarylindenes bind with high affinity to the ER subtypes and demonstrate a range of different biological activities, both in transcriptional reporter gene assays and inhibition of estradiol-stimulated proliferation of MCF-7 cells. Several ligands differentiate between ER alpha and ER beta subtypes at an estrogen response element (ERE), displaying various levels of partial to full agonist activity at ER alpha, while antagonizing estradiol action at ER beta.

  DOI：

  10.1021/jm050226i
• 作为产物：
  描述：

  对甲氧基苯乙酸 在 三氯化铝 、 草酰氯 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 6-methoxy-2-(4-methoxy-phenyl)-3-phenyl-indene
  参考文献：
  名称：

  Differential Response of Estrogen Receptor Subtypes to 1,3-Diarylindene and 2,3-Diarylindene Ligands

  摘要：

  Estrogen receptors (ERs) control transcription of genes important for normal human development and reproduction. The signaling networks are complex, and there is a need for a molecular level understanding of the roles of receptor subtypes ER alpha and ER beta in normal physiology and as therapeutic targets. We synthesized two series of ER ligands, based on a common indene scaffold, in an attempt to develop compounds that can selectively modulate ER-mediated transcription. The 3-ethyl-1,2-diarylindenes, utilizing an amide linker for the 1-aryl extension, bind weakly to the ERs. The 2,3-diarylindenes bind with high affinity to the ER subtypes and demonstrate a range of different biological activities, both in transcriptional reporter gene assays and inhibition of estradiol-stimulated proliferation of MCF-7 cells. Several ligands differentiate between ER alpha and ER beta subtypes at an estrogen response element (ERE), displaying various levels of partial to full agonist activity at ER alpha, while antagonizing estradiol action at ER beta.

  DOI：

  10.1021/jm050226i

文献信息

• Selective Divergent Synthesis of Indanols, Indanones, and Indenes via Acid-Mediated Cyclization of (<i>Z</i>)- and (<i>E</i>)-(2-Stilbenyl)methanols and Its Application for the Synthesis of Paucifloral F Derivatives
  作者：Jira Jongcharoenkamol、Patsapon Chuathong、Yuka Amako、Masato Kono、Kasam Poonswat、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1021/acs.joc.8b01921

  日期：2018.11.2

  structurally related to the natural product paucifloral F. At higher temperatures, 1,2- and 2,3-disubstituted indenes could be selectively prepared in good to excellent yields. On the other hand, the (Z)-stilbenes, under similar conditions (PTS-Si), did not give the indanols; only the 1,2-disubstituted indenes could be obtained. To gain further insights into the stereochemistry at C2–C3 for the (Z)-stilbenes

  选自溴/碘苯甲醛衍生物，相应的（起始ž和（ - ）ë） - （2-芪）基甲醇可以在步骤2-5通过Pd-催化的交叉偶联反应制备（的Sonogashira和Heck反应），接着加入芳基锂/芳基格氏添加剂。对于（E）-斯蒂苯，随后在低温下使用固定在二氧化硅（PTS-Si）上的对-TsOH进行酸介导的环化反应，可得到2,3-反式在C2-C3处具有完全立体控制的-1-茚满醇。醇的进一步氧化提供了茚满酮，其在结构上与天然产物古朴的F有关。在较高的温度下，可以选择性地以良好至优异的产率制备1,2-和2,3-二取代的茚满。另一方面，在相似的条件下（PTS-Si），（Z）-苯乙烯基苯甲酸酯没有得到茚满醇；相反，（D）-Stilbenes没有得到茚满醇。只能得到1,2-二取代的茚。为了进一步了解（Z）-对甲磺胺在C2-C3的立体化学，采用氢化物或叠氮化物作为亲核试剂。相应的茚满产物在C2-C3处以顺式立体化学
• THE SYNTHESIS OF SOME INDENE AND DIHYDRONAPHTHALENE DERIVATIVES RELATED TO STILBESTROL
  作者：MILTON SILVERMAN、MARSTON TAYLOR BOGERT

  DOI：10.1021/jo01171a006

  日期：1946.1