(+/-)-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin | 866639-21-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: (+/-)-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin
• 英文别名: 3,4-dihydro-5,7-dimethoxy-4-(4-methoxyphenyl)coumarin；5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin；5,7-dimethoxy-4-(4-methoxyphenyl)chroman-2-one；5,7-Dimethoxy-4-(4-methoxyphenyl)-3,4-dihydrochromen-2-one
• CAS: 866639-21-6
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: COOUEGPUMYEYNP-UHFFFAOYSA-N

物化性质

• 熔点：
  133.3-133.8 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  442.0±45.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以79%的产率得到3,4-dihydro-4-(4'-hydroxyphenyl)-5,7-dihydroxycoumarin
  参考文献：
  名称：

  Regioselective synthesis and estrogenicity of (±)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins

  摘要：

  Nine new (+/-)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins have been synthesized from 2,4,6-trimethoxybenzaldehyde via a short, efficient, and regioselective pathway, together with the unsubstituted analogue (+/-)-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarin. The compounds were tested for estrogenic activity using a yeast-based estrogen screen. Weak estrogenicity was determined for seven members of the series. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.010
• 作为产物：
  描述：

  3,5-二甲氧基苯酚 、 反式-4-甲氧基肉桂酸 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到(+/-)-5,7-dimethoxy-4-(4-methoxyphenyl)-3,4-dihydrocoumarin
  参考文献：
  名称：

  从苯酚和肉桂酸衍生物方便地合成二氢香豆素

  摘要：

  描述了合成二氢香豆素衍生物的简便方法。尽管发现在Pd（OAc）2存在下，苯酚与丙烯酸酯在三氟乙酸中反应生成香豆素的产物的收率很低，但在没有Pd（OAc）的情况下，二氢香豆素衍生物的收率高到高。 ）2当在该反应中使用带有给电子基团的肉桂酸乙酯时。

  DOI：

  10.1016/j.tet.2005.07.062

文献信息

• Hexafluoroisopropanol and Acetyl Chloride Promoted Catalytic Hydroarylation with Phenols
  作者：Sudeshna Roy、Hashim F. Motiwala、Karl M. Koshlap、Jeffrey Aubé

  DOI：10.1002/ejoc.201701256

  日期：2018.1.23

  HFIP facilitates the mild catalytic hydroarylation of phenols to provide dihydrocoumarins using sub‐stoichiometric amounts of acetyl chloride as catalyst.

  HFIP促进了酚的轻度催化加氢芳基化反应，从而使用亚化学计量的乙酰氯作为催化剂提供了二氢香豆素。
• Stereochemical Control in the Reduction of 2-Chromanols
  作者：Kelin Li、Kumar Vanka、Ward H. Thompson、Jon A. Tunge

  DOI：10.1021/ol061727g

  日期：2006.10.1

  silane reductants and 2,4-trans-chromans using the smaller silane PhSiH(3). The stereochemical outcome has been rationalized on the basis of a Curtin-Hammett kinetic situation arising from hydride delivery to two different conformations of an intermediate oxocarbenium ion. This method provides a powerful way to control the relative stereochemistry of these substructures which are prevalent in bioactive

  [反应：见正文]还原C5取代的2-羟基苯并二氢吡喃选择性地使用较大的硅烷还原剂提供2,4-顺式苯并二氢吡喃，并使用较小的硅烷PhSiH（3）进行2,4-反式-苯并二氢吡喃。立体化学结果已根据Curtin-Hammett动力学情况进行了合理化，该动力学情况是由氢化物传递至中间体氧碳鎓离子的两个不同构象而引起的。该方法提供了一种有效的方法来控制这些在生物活性天然产物中普遍存在的亚结构的相对立体化学。
• Yb(OTf)₃-Catalyzed Reactions of 5-Alkylidene Meldrum's Acids with Phenols:  One-Pot Assembly of 3,4-Dihydrocoumarins, 4-Chromanones, Coumarins, and Chromones
  作者：Eric Fillion、Aaron M. Dumas、Bryan A. Kuropatwa、Neil R. Malhotra、Tamsyn C. Sitler

  DOI：10.1021/jo052000t

  日期：2006.1.1

  Yb(OTf)3-catalyzed annulation reactions of phenols with 5-alkylidene Meldrum's acids enabled the synthesis of structurally diverse heterocycles in high isolated yields. A series of 4-substituted 3,4-dihydrocoumarins, 2,2-disubstituted 4-chromanones, coumarins, and 2-substituted chromones were readily and efficiently assembled, including the naturally occurring coumarins citropten, scoparone, and ayapin

  Yb（OTf）3催化的苯酚与5-亚烷基Meldrum酸的环化反应能够以高分离产率合成结构多样的杂环。一系列4-取代的3,4-二氢香豆素，2,2-二取代的4-发色酮，香豆素和2-取代的色酮容易而有效地组装，包括天然存在的香豆素香茅素，香柏酮和阿平。将苯酚添加到双亲电子性5-亚烷基Meldrum的酸中，通过两种不同的多键形成方式进行：弗里德-克拉夫特C-烷基化/ O-酰化和弗里德-克拉夫特C-酰化/ O-烷基化。催化环化反应的区域选择性由亚烷基部分上的取代度控制。
• Small molecule amides as potent ROR-γ selective modulators
  作者：Pasha M. Khan、Bahaa El-Dien M. El-Gendy、Naresh Kumar、Ruben Garcia-Ordonez、Li Lin、Claudia H. Ruiz、Michael D. Cameron、Patrick R. Griffin、Theodore M. Kamenecka

  DOI：10.1016/j.bmcl.2012.11.025

  日期：2013.1

  The structure-activity relationship study of a diphenylpropanamide series of ROR-gamma selective modulators is reported. Compounds were screened using chimeric receptor Gal4 DNA-binding domain (DBD)-NR ligand binding domain cotransfection assay in a two-step format. Three different regions of the scaffold were modified to assess the effects on repression of ROR-gamma transcriptional activity and potency. The lead compound 1 exhibits modest mouse pharmacokinetics and an acceptable in vitro profile which makes it a suitable in vivo probe to interrogate the functions of ROR-gamma in animal models of disease. (C) 2012 Elsevier Ltd. All rights reserved.
• Reduction of Pyrrolyl- and Indolylamides with BH₃·THF: Cyclodeoxygenation versus Deoxygenation
  作者：Kelin Li、Jon A. Tunge

  DOI：10.1021/jo801627z

  日期：2008.11.7

  Herein we report that borane reductions of acylpyrroles and acylindoles that contain a pendant phenol take two different paths. Acylpyrroles undergo a reductive cyclization to make unusual chromanyl pyrroles. Treatment of related acylindoles under identical conditions results in deoxygenation without cyclization. The results are interpreted in terms of relative rates of cyclization and reduction of intermediate carbenium ions, where cyclization of the indole-stablized carbenium ion is slower.