6-氯-4-羟基-7-甲基香豆素 | 64729-38-0

• 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
• 中文名称: 6-氯-4-羟基-7-甲基香豆素
• 英文名称: 6-chloro-4-hydroxy-7-methylcoumarin
• 英文别名: 6-Chloro-4-hydroxy-7-methyl-2H-chromen-2-one；6-chloro-4-hydroxy-7-methylchromen-2-one
• CAS: 64729-38-0
• 化学式: C₁₀H₇ClO₃
• 分子量: 210.617
• InChiKey: WOILRPBEBXTBKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  6-氯-4-羟基-7-甲基香豆素 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 2-(4-hydroxy-6-chloro-7-methyl-2-oxo-2H-chromene-3-yl)-8-chloro-7-methyl-4H-furo[3,2-c]chromene-4-one
  参考文献：
  名称：

  Synthesis and Anti-inflammatory Activity of Novel Furochromenes

  摘要：

  A series of variously substituted furochromenes, hemiacetals 2, acetals 3, and rearranged compounds 4, were synthesized from variously substituted 4-hydroxycoumarins and evaluated in several in vitro assays, inhibition of mast cell degranulation induced by the activation of FCE receptor type I or calcium ionophore and leukotriene B-4 (LTB4) inhibition. The most active derivatives, 3p and 4p (8-iso-propyl substitution in coumarin ring) and 3r (5-methyl-8-chloro substitution), showed significant inhibition of mast cell degranulation (Fc epsilon-triggered) and LTB4, and exhibited significant local anti-inflammatory activity in PMA induced ear edema in CD1 mice, with potency equal (compounds 3p and 4p) or better (compound 3r) in comparison with zileuton, a reference drug used. It might be a promising direction for developing novel drugs as potential agents for the treatment of allergies and other inflammatory diseases.

  DOI：

  10.5562/cca2240
• 作为产物：
  描述：

  4-氯-3-甲基苯酚 、 丙二酸 在 zinc(II) chloride 、 三氯氧磷 作用下， 生成 6-氯-4-羟基-7-甲基香豆素
  参考文献：
  名称：

  Improved and rapid synthesis of new coumarinyl chalcone derivatives and their antiviral activity

  摘要：

  Two closely structurally related coumarins, 4-hydroxy-8-isopropyl-5-methylcoumarin and 4-hydroxy-6-chloro-7-methylcoumarin were acylated at C-3 and further converted to the respective chalcones and two series of eighteen new compounds, which were evaluated for possible antiviral activity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.175

文献信息

• Coumarin to Isocoumarin: One-Pot Synthesis of 3-Substituted Isocoumarins from 4-Hydroxycoumarins and Benzyne Precursors
  作者：Kashmiri Neog、Dhiraj Dutta、Babulal Das、Pranjal Gogoi

  DOI：10.1021/acs.orglett.7b00027

  日期：2017.2.3

  direct synthesis of 3-substituted isocoumarin from 4-hydroxycoumarin and a benzyne precursor is developed. This synthetic strategy proceeds via C–O and C–C bond cleavage as well as C–O and C–C bond formations in a single reaction vessel by simple treatment with CsF in the absence of catalyst. This methodology affords moderate to good yields of 3-substituted isocoumarins and is tolerant of a variety of

  开发了由4-羟基香豆素和苯炔前体的新型无过渡金属直接合成3-取代的香豆素。通过在不存在催化剂的情况下用CsF进行简单处理，即可在单个反应容器中通过C–O和C–C键断裂以及C–O和C–C键形成过程进行合成。该方法提供了中等至良好产率的3-取代的异香豆素，并且耐受包括卤化物在内的多种官能团。
• [EN] SUBSTITUTED FUROCHROMENE COMPOUNDS OF ANTIINFLAMMATORY ACTION<br/>[FR] COMPOSES DE FUROCHROMENE SUBSTITUES A ACTION ANTI-INFLAMMATOIRE
  申请人：PLIVA ISTRAZIVACKI INST D O O

  公开号：WO2005010006A1

  公开（公告）日：2005-02-03

  The present invention relates to novel compounds of the formula (I) including all stereoisomers and tautomers, to the pharmaceutically acceptable salts and solvates thereof, to the processes and reactive intermediates for their preparation and to their use in the prophylaxis and treatment of asthma and other inflammatory diseases and/or conditions in humans.

  本发明涉及公式（I）的新化合物，包括所有立体异构体和互变异构体，以及其药用可接受盐和溶剂合物，用于预防和治疗人类的哮喘和其他炎症性疾病和/或情况的过程和反应中间体，以及它们的使用。
• Pd-Catalyzed cross-coupling synthesis of 4-aryl-3-formylcoumarins
  作者：Maddali L. N. Rao、Sachchida Nand

  DOI：10.1039/d1ob02016a

  日期：——

  The threefold cross-coupling of triarylbismuth reagents with 4-chloro-3-formylcoumarins furnished the corresponding 4-aryl-3-formylcoumarins in a chemoselective manner with high yields under Pd-catalyzed conditions. This method was successfully applied to electronically different triarylbismuth reagents and 4-chloro-3-formylcoumarins preserving the 3-formyl group in the coumarin scaffold.

  三芳基铋试剂与 4-氯-3-甲酰基香豆素的三重交叉偶联以化学选择性方式在 Pd 催化条件下以高产率提供了相应的 4-芳基-3-甲酰基香豆素。该方法成功地应用于电子不同的三芳基铋试剂和保留香豆素支架中3-甲酰基的4-氯-3-甲酰基香豆素。
• Substituted furochromene compounds of antiinflammatory action
  申请人：Mercep Mladen

  公开号：US20060148890A1

  公开（公告）日：2006-07-06

  The present invention relates to novel compounds of the formula (I) including all stereoisomers and tautomers thereof, to the pharmaceutically acceptable salts and solvates thereof, to the processes and reactive intermediates for their preparation and to their use in the prophylaxis and treatment of asthma and other inflammatory diesases and/or conditions in humans.

  本发明涉及式（I）的新化合物，包括其所有立体异构体和互变异构体、药学上可接受的盐和溶剂合物，以及其制备过程和反应中间体，以及它们在预防和治疗人类哮喘和其他炎症性疾病和/或病况中的用途。
• Use of 4-Cyanocoumarins as Dienophiles in a Facile Synthesis of Highly Substituted Dibenzopyranones
  作者：Michael E. Jung、Damian A. Allen

  DOI：10.1021/ol802792g

  日期：2009.2.5

  A new synthesis of dibenzopyranones 14 is reported via the Diels-Alder cycloaddition of 4-cyanocoumarins 12 with 1-silyloxydienes 10 to give the adducts 13 which are then converted into 14 in one step via treatment with base and loss of the cyano and silyloxy groups.