6-bromo-2-oxo-2H-chromene-3-carbaldehyde | 108734-14-1

• 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: 6-bromo-2-oxo-2H-chromene-3-carbaldehyde
• 英文别名: 6-bromo-3-formylcoumarin；6-bromo-2-oxochromene-3-carbaldehyde
• CAS: 108734-14-1
• 化学式: C₁₀H₅BrO₃
• 分子量: 253.052
• InChiKey: ZMODGAASZKLLDT-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：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-2-oxo-2H-chromene-3-carbaldehyde 在 4-二甲氨基吡啶 、 三丁基膦 、 乙酸酐 、 三乙胺 、 L-脯氨酸 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 6-bromo-3-(2-phenyl-4,5,6,7-tetrahydrobenzofuran-3-yl)-2H-chromen-2-one
  参考文献：
  名称：

  通过分子内Wittig反应 合成呋喃[3,4- c ]香豆素和相关的呋喃香豆素衍生物†

  摘要：

  已经开发了一种新的，通用的功能性呋喃[3,4- c ]香豆素和相关呋喃香豆香豆素衍生物的新策略，该策略基于从α，β-不饱和酮开始的极其容易的分子内Wittig反应，三丁基膦和酰氯。有人提出磷化磷是构成关键呋喃环的关键中间体，一步就可以制得各种各样的呋喃香豆素。

  DOI：

  10.1039/c1ob06571h
• 作为产物：
  描述：

  tert-butyl 3-(5-bromo-2-hydroxyphenyl)-3-hydroxy-2-methylenenpropanoate 在 selenium(IV) oxide 、 氢碘酸 、 乙酸酐 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.0h， 生成 6-bromo-2-oxo-2H-chromene-3-carbaldehyde
  参考文献：
  名称：

  Convenient Synthesis of 3-Methylcoumarins and Coumarin-3-carbaldehydes

  摘要：

  Rapid, microwave-assisted Baylis-Hillman reactions of substituted salicylaldehydes, followed by one-pot hydrogen iodide-mediated cyclization and reduction of the corresponding adducts, has afforded 3-methylcoumarins in up to 94% yield in the final step. Subsequent microwave-assisted selenium dioxide oxidation of selected 3-methylcoumarins has provided convenient access to the corresponding coumarin-3-carbaldehydes and permitted a significant improvement over the yield obtained using conventional heating.

  DOI：

  10.1080/00397911.2010.523491

文献信息

• An Easy Conversion of 2<i>H</i>-Chromenes into Coumarins. An Entry to 3-Formyl Coumarins
  作者：Loïc Rene、Alain Lefebvre、Gilles Auzou

  DOI：10.1055/s-1986-31707

  日期：——

  3-Formyl coumarins 4 are easily prepared by conversion of 3-cyano-2-morpholino-2H-chromenes 1 in boiling aqueous hydrochloric acid.This transformation occurs in two steps from salicylaldehydes.

  3-甲酰基香豆素 4 很容易通过在沸腾的盐酸水溶液中转化 3-氰基-2-吗啉代-2H-色烯 1 来制备。该转化由水杨醛分两步进行。
• CRTH2 Receptor Ligands For Medicinal Uses
  申请人：Ulven Trond

  公开号：US20090099189A1

  公开（公告）日：2009-04-16

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis, wherein A represents a carboxyl group —COON, or a carboxyl bioisostere; A 1 , is hydrogen or methyl; ring Ar 1 is an optionally substituted phenyl ring 5- or 6-membered monocyclic heteroaryl ring, in which AA 1 CHO— and L2 are linked to adjacent ring atoms; rings Are 2 , Ar 3 each independently represent a phenyl or 5- or 6-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; t is 0 or 1; L2 and L3 are linker radicals as defined in the description.

  式(I)的化合物可用于治疗对CRTH2受体活性调节敏感的疾病，例如哮喘、鼻炎、过敏性气道综合症和过敏性鼻支气管炎，其中A代表羧基—COON或羧基生物同位素；A1为氢或甲基；环Ar1是一个可选取代的苯环5-或6-成员的单环杂环，其中AA1CHO—和L2与相邻的环原子连接；环Are2，Ar3各自独立地表示一个苯环或5-或6-成员的单环杂环，或由一个5-或6-成员的碳环或杂环组成的双环系统，该环或环系统被苯并或与一个5-或6-成员的单环杂环融合，该环或环系统是可选取代的；t为0或1；L2和L3是如描述中所定义的连接基团。
• CRTH2 receptor ligands for medicinal uses
  申请人：Ulven Trond

  公开号：US20110269763A1

  公开（公告）日：2011-11-03

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis: wherein A represents a carboxyl group —COOH, or a carboxyl bioisostere; A 1 is hydrogen or methyl; ring Ar 1 is an optionally substituted phenyl ring or 5- or 6-membered monocyclic heteroaryl ring, in which AA 1 CHO— and L2 are linked to adjacent ring atoms; rings Ar 2 , Ar 3 each independently represent a phenyl or 5- or 6-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; t is 0 or 1; L2 and L3 are linker radicals as defined in the description.

  式(I)的化合物可用于治疗对CRTH2受体活性调节敏感的疾病，例如哮喘、鼻炎、过敏性气道综合症和过敏性鼻支气管炎：其中A代表羧基—COOH或羧基生物同位素；A1为氢或甲基；环Ar1为可选取代的苯环或5-或6-成员的单环杂环，其中AA1CHO—和L2连接到相邻的环原子上；环Ar2、Ar3各自独立地表示苯环或5-或6-成员的单环杂环，或由5-或6-成员的碳环或杂环组成的双环系统，该环或环系统是苯并或与5-或6-成员的单环杂环融合，该环或环系统是可选的取代；t为0或1；L2和L3是如描述中定义的连接基。
• CRTH2 Receptor Ligands for Medical Use
  申请人：7TM Pharma A/S

  公开号：EP2336113A1

  公开（公告）日：2011-06-22

  4-Bromo-2-[1-(2,6-dichlorophenyl)-1H-pyrazole-4-carbonyl]phenoxyl acetic acid is useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis.

  4-溴-2-[1-（2,6-二氯苯基）-1H-吡唑-4-甲酰基]苯氧乙酸可用于治疗对调节 CRTH2 受体活性有反应的疾病，如哮喘、鼻炎、过敏性气道综合征和过敏性鼻支气管炎。
• CRTH2 RECEPTOR LIGANDS FOR MEDICINAL USES
  申请人：7TM Pharma A/S

  公开号：EP1758579A1

  公开（公告）日：2007-03-07