8-bromo-5,7-dimethoxycoumarin | 299184-53-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-bromo-5,7-dimethoxycoumarin
• 英文别名: 8-Bromo-5,7-dimethoxy-chromen-2-one；8-bromo-5,7-dimethoxychromen-2-one
• CAS: 299184-53-5
• 化学式: C₁₁H₉BrO₄
• 分子量: 285.094
• InChiKey: LXMVUTRBEJLMRM-UHFFFAOYSA-N

物化性质

• 熔点：
  226-227 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  438.5±45.0 °C(Predicted)
• 密度：
  1.572±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(甲氧基甲烯基)-2,2-二甲基-1,3-二氧己环-4,6-二酮 、 2-溴-3,5-二甲氧基苯酚 在 ytterbium(III) triflate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 以67%的产率得到8-bromo-5,7-dimethoxycoumarin
  参考文献：
  名称：

  Yb（OTf）3 -5-亚烷基Meldrum酸与苯酚的催化反应：3,4-二氢香豆素，4-色曼酮，香豆素和色酮的一锅组装。

  摘要：

  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。

  DOI：

  10.1021/jo052000t

文献信息

• Atom Economy. Palladium-Catalyzed Formation of Coumarins by Addition of Phenols and Alkynoates via a Net C−H Insertion
  作者：Barry M. Trost、F. Dean Toste、Kevin Greenman

  DOI：10.1021/ja0286573

  日期：2003.4.1

  A strategy to achieve ortho substitution of phenols initiated by an ortho-palladation to create coumarins was examined. Indeed, treatment of alkynoates with electron-rich phenols in the presence of a palladium catalyst and an acid does generate coumarins. The scope of the reaction with respect to the phenol and the alkynoates is defined. With unsymmetrical aromatic substrates, generally good regioselectivity that reflects the HOMO coefficients can be observed. In the course of these studies, numerous important naturally occurring coumarins have been synthesized, including fraxinol methyl ether, ayapin, herniarin, xanthoxyletin, and alloxanthoxyletin. The fact that a Pd(0) is the precatalyst rather than a Pd(+2) species and that an acid that reduces Pd(+2) salts, formic acid, functions better than other carboxylic acids raises doubts about the initial working hypothesis. A novel mechanism involving a palladium phenoxide formed from a hydridopalladium carboxylate and phenol is invoked to rationalize the results.
• [EN] ALDO-KETO REDUCTASE SUBFAMILY 1C3 (AKR1C3) INHIBITORS<br/>[FR] INHIBITEURS DE LA SOUS-FAMILLE 1C3 D'ALDO-CÉTO RÉDUCTASE (AKR1C3)
  申请人：GTX INC

  公开号：WO2013142390A1

  公开（公告）日：2013-09-26

  The present invention relates to a novel class of AKR1C3 inhibitors, to compositions containing them, to methods for their preparation, and to methods of use thereof. The AKR1C3 inhibitors may be useful in the treatment of, for example, prostate cancer, benign prostate hyperplasia (BPH), lung cancer, acne, seborrhea, hirsutism, baldness, alopecia, precocious puberty, adrenal hypertrophy, polycystic ovary syndrome, breast cancer, uterine cancer, uterine fibroids, endometriosis, myeloma and leiomyoma.
• 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。