7-methoxy-2-(3-methoxyphenyl)chroman-4-one | 32272-16-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-methoxy-2-(3-methoxyphenyl)chroman-4-one
• 英文别名: 3',7-Dimethoxyflavanone；7-methoxy-2-(3-methoxy-phenyl)-chroman-4-one；7-Methoxy-2-(3-methoxy-phenyl)-chroman-4-on；7-Methoxy-2-(3-methoxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 32272-16-5
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: MMYGVQSTLRGGMP-UHFFFAOYSA-N

物化性质

• 熔点：
  104 °C
• 沸点：
  465.4±45.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methoxy-2-(3-methoxyphenyl)chroman-4-one 在 五氯化磷 、 氢碘酸 、 乙酸酐 、 苯 作用下， 生成 3,7-二羟基-2-苯基-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  Hattori, Acta Phytochimica, 1932, vol. 6, p. 131,152

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 硫酸 作用下， 生成 7-methoxy-2-(3-methoxyphenyl)chroman-4-one
  参考文献：
  名称：

  v. Kostanecki; Widmer, Chemische Berichte, 1904, vol. 37, p. 4159

  摘要：

  DOI：

文献信息

• Mild and Efficient One-Pot Synthesis of Diverse Flavanone Derivatives via an Organocatalyzed Mannich-Type Reaction
  作者：Yong Lee、Srinivasu Vuppalapati、Likai Xia、Naushad Edayadulla

  DOI：10.1055/s-0033-1340466

  日期：——

  Abstract A facile ethylenediamine diacetate (EDDA)-catalyzed one-pot synthesis of biologically interesting flavanone derivatives from 2-hydroxyacetophenones, aromatic aldehydes, and aniline via a Mannich-type reaction is described. This synthetic method provides a rapid access to biologically interesting flavanone derivatives. To demonstrate this method, several biologically interesting natural products

  摘要 描述了一种简便的乙二胺二乙酸酯（EDDA）催化通过曼尼希型反应从2-羟基苯乙酮，芳族醛和苯胺进行一锅式合成生物学上令人感兴趣的黄烷酮衍生物的方法。这种合成方法可快速获得生物学上令人感兴趣的黄烷酮衍生物。为了证明该方法，合成了带有黄烷酮部分的几种生物学上有趣的天然产物，它们是外消旋体。 描述了一种简便的乙二胺二乙酸酯（EDDA）催化通过曼尼希型反应从2-羟基苯乙酮，芳族醛和苯胺进行一锅式合成生物学上令人感兴趣的黄烷酮衍生物的方法。这种合成方法可快速获得生物学上令人感兴趣的黄烷酮衍生物。为了证明该方法，合成了带有黄烷酮部分的几种生物学上有趣的天然产物，它们是外消旋体。
• Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold
  作者：Brian M. Muller、Jesse Mai、Reid A. Yocum、Marc J. Adler

  DOI：10.1039/c4ob00398e

  日期：——

  The impact of substitution on a novel colorimetric dynamic covalent switching scaffold was investigated using UV/Vis and NMR spectroscopy.

  通过紫外/可见光谱和核磁共振谱，研究了替代对一种新型比色动态共价开关支架的影响。
• Utilization of “2-Pyrrolidone Hydrotribromide” in the Synthesis of Flavones
  作者：Noboru Takeno、Tohoru Fukushima、Shin-ichi Takeda、Kazuyasu Kishimoto

  DOI：10.1246/bcsj.58.1599

  日期：1985.5

  The reaction of flavanone with “2-pyrrolidone hydrotribromide” in tetrahydrofuran gave 3-bromoflavanone in a good yield. On the other hand, flavone was obtained in 97% yield when this reaction was carried out in dimethyl sulfoxide at 80 °C. Under the same conditions, most flavones were obtained from the corresponding flavanones in high purity and good yields.

  在四氢呋喃中，黄酮与“2-吡咯烷酮三溴化物”的反应得到了3-溴黄酮，并且产率良好。另一方面，当在80°C下的二甲基亚砜中进行此反应时，得到了97%的黄酮。在相同条件下，大多数黄酮从相应的黄酮中以高纯度和良好产率获得。
• ——
  作者：Christelle Pouget、Catherine Fagnere、Jean‐Philippe Basly、Anne‐Elise Besson、Yves Champavier、Gerard Habrioux、Albert‐Jose Chulia

  DOI：10.1023/a:1014490817731

  日期：——

  Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors: therefore. in an effort to develop novel anti breast cancer agents. B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern.Methods. A series of flavanones was prepared by cyclisation of 2'-hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity or these compounds was investigated using human placental microsomes and radiolabeled [1.2,6,7-H-3]-androstenedione as substrate.Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring subtitution pattern. Hydroxylation at position 3' and/or 4' enhanced the anti-aromatase activity thus, 3'.4'-dihydroxy-7-methoxyflavanone was found to he twice more potent than aminoglutethimide. the first aromatase inhibitor clinically used.Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these Compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.
• Imafuku, Kimiaki; Honda, Masaaki; McOmie, J. F. W., Synthesis, 1987, # 2, p. 199 - 201
  作者：Imafuku, Kimiaki、Honda, Masaaki、McOmie, J. F. W.

  DOI：——

  日期：——