4-(difluoromethoxy)-3,5-dimethoxybenzaldehyde | 446270-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(difluoromethoxy)-3,5-dimethoxybenzaldehyde
• CAS: 446270-61-7
• 化学式: C₁₀H₁₀F₂O₄
• mdl: MFCD02656321
• 分子量: 232.184
• InChiKey: CDASCEKDGKTDOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(difluoromethoxy)-3,5-dimethoxybenzaldehyde 、 2-(羧基乙酰氨基)苯甲酸 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以51%的产率得到(E)-2-[[4-(difluoromethoxy)-3,5-dimethoxyphenyl-1-oxo-2-propenyl]amino]benzoic acid
  参考文献：
  名称：

  3′,4′-Bis-difluoromethoxycinnamoylanthranilate (FT061): An orally-active antifibrotic agent that reduces albuminuria in a rat model of progressive diabetic nephropathy

  摘要：

  Cinnamoylanthranilates including tranilast have been identified as promising antifibrotics that can reduce fibrosis occurring in the kidney during diabetes, thereby delaying and/or preventing kidney dysfunction. Structure-activity relationships aimed at improving potency and metabolic stability have led to the discovery of FT061. This compound, which bears a bis-difluoromethoxy catechol, attenuates TGF-beta-stimulated production of collagen in cultured renal mesangial cells (approx 50% at 3 mu M). When dosed orally at 20 mg/kg to male Sprague Dawley rats, FT061 exhibited a high bioavailability (73%), C-max of 200 mu M and T-max of 150 min, and a half-life of 5.4 h. FT061 reduced albuminuria when orally dosed in rats at 200 mg kg/day in a late intervention study of a rat model of progressive diabetic nephropathy. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.100
• 作为产物：
  描述：

  2-氯-2,2-二氟乙酸甲酯 、 丁香醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以39%的产率得到4-(difluoromethoxy)-3,5-dimethoxybenzaldehyde
  参考文献：
  名称：

  [EN] HALOGENATED ANALOGUES OF ANTI-FIBROTIC AGENTS
  [FR] ANALOGUES HALOGÉNÉS D'AGENTS ANTIFIBROTIQUES

  摘要：

  本发明涉及具有规定的取代基的式(I)的卤代化合物。这些化合物可能作为抗纤维化剂有用。本发明还涉及它们的制备方法。

  公开号：

  WO2009079692A1

文献信息

• [EN] SYNTHESIS OF DIFLUOROMETHYL ETHERS AND SULFIDES<br/>[FR] SYNTHÈSE DE DIFLUOROMÉTHYLÉTHERS ET DE DIFLUOROMÉTHYLSULFURES
  申请人：UNIV CALIFORNIA

  公开号：WO2014107380A1

  公开（公告）日：2014-07-10

  The synthesis of difluoromethyl ethers and sulfides with a simple, non-ozone- depleting reagent is described. The difluoromethylation of phenols with this reagent occurs at room temperature within minutes with exceptional functional group tolerance. The mild conditions makes possible tandem processes for the conversion of aryl boronic acids, aryl halides and arenes to difluoromethyl ethers. Mechanistic studies support a reaction pathway involving nucleophilic attack of the phenolate to difluorocarbene.

  描述了使用一种简单、无臭氧破坏剂的方法合成二氟甲基醚和硫醚。使用这种试剂对酚进行二氟甲基化反应在室温下几分钟内就能完成，并且具有异常的官能团容忍性。温和的条件使得可能进行串联过程，将芳基硼酸、芳基卤代烃和芳烃转化为二氟甲基醚。机理研究支持一个涉及酚酚根攻击二氟卡宾的反应途径。
• [EN] HALOGENATED ANALOGUES OF ANTI-FIBROTIC AGENTS<br/>[FR] ANALOGUES HALOGÉNÉS D'AGENTS ANTIFIBROTIQUES
  申请人：FIBROTECH THERAPEUTICS PTY LTD

  公开号：WO2009079692A1

  公开（公告）日：2009-07-02

  The present invention relates to halogenated compounds of formula (I) with the substituents as described within the specification. The compounds may be useful as anti-fibrqtic agents. The present invention also relates to methods for their preparation.

  本发明涉及具有规定的取代基的式(I)的卤代化合物。这些化合物可能作为抗纤维化剂有用。本发明还涉及它们的制备方法。
• HALOGENATED ANALOGUES OF ANTI-FIBROTIC AGENTS
  申请人：Kelly Darren James

  公开号：US20120059188A9

  公开（公告）日：2012-03-08

  The present invention relates to halogenated compounds of formula (I) with the substituents as described within the specification. The compounds may be useful as anti-fibrotic agents. The present invention also relates to methods for their preparation.

  本发明涉及式(I)的卤代化合物，所述化合物的取代基如规范中所述。该化合物可以用作抗纤维化剂。本发明还涉及其制备方法。
• Halogenated analogues of anti-fibrotic agents
  申请人：Kelly Darren James

  公开号：US08624056B2

  公开（公告）日：2014-01-07

  The present invention relates to halogenated compounds of formula (I) with the substituents as described within the specification. The compounds may be useful as anti-fibrotic agents. The present invention also relates to methods for their preparation.

  本发明涉及公式（I）的卤代化合物，其取代基在规范中描述。这些化合物可能有用作为抗纤维化剂。本发明还涉及其制备方法。
• SYNTHESIS OF DIFLUOROMETHYL ETHERS AND SULFIDES
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20150336866A1

  公开（公告）日：2015-11-26

  The synthesis of difluoromethyl ethers and sulfides with a simple, non-ozone-depleting reagent is described. The difluoromethylation of phenols with this reagent occurs at room temperature within minutes with exceptional functional group tolerance. The mild conditions makes possible tandem processes for the conversion of aryl boronic acids, aryl halides and arenes to difluoromethyl ethers. Mechanistic studies support a reaction pathway involving nucleophilic attack of the phenolate to difluorocarbene.