4-hydroxy-3-(4-methoxyphenyl)-5-methylfuran-2(5H)-one | 1019196-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-hydroxy-3-(4-methoxyphenyl)-5-methylfuran-2(5H)-one
• 英文别名: 3-hydroxy-4-(4-methoxyphenyl)-2-methyl-2H-furan-5-one
• CAS: 1019196-87-2
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: POVFCDYDWYRKIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-(4-methoxyphenyl)-5-methylfuran-2(5H)-one 在 sodium methylate 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 生成 (3-methoxy-4-(4-methoxyphenyl)-2-methyl-5-oxo-2,5-dihydrofuran-2-yl)methyl methanesulfonate
  参考文献：
  名称：

  Synthesis and anti-BVDV activity of novel δ-sultones in vitro: Implications for HCV therapies

  摘要：

  In this study we report the synthesis and activity against bovine viral diarrhea virus (BVDV) of a novel series of bicycle delta-sultones containing gamma-lactones. BVDV is responsible for major losses in cattle. Some of the synthesized delta-sultones showed pronounced anti-BVDV activity with EC50 values of 0.12-1.0 mu M and no significant cytotoxicity. Among them, the ortho bromosubstituted derivative 4f (EC50 = 0.12 mu M) showed better antiviral activity than other derivatives and was 10 fold more that of than positive control ribavirin (EC50 = 1.3 mu M). BVDV is also considered to be a valuable surrogate for the hepatitis C virus (HCV) in antiviral drug studies. The above results provided a novel candidate for the development of anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.012
• 作为产物：
  描述：

  对甲氧基苯乙酸 在 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 4-hydroxy-3-(4-methoxyphenyl)-5-methylfuran-2(5H)-one
  参考文献：
  名称：

  Synthesis and anti-BVDV activity of novel δ-sultones in vitro: Implications for HCV therapies

  摘要：

  In this study we report the synthesis and activity against bovine viral diarrhea virus (BVDV) of a novel series of bicycle delta-sultones containing gamma-lactones. BVDV is responsible for major losses in cattle. Some of the synthesized delta-sultones showed pronounced anti-BVDV activity with EC50 values of 0.12-1.0 mu M and no significant cytotoxicity. Among them, the ortho bromosubstituted derivative 4f (EC50 = 0.12 mu M) showed better antiviral activity than other derivatives and was 10 fold more that of than positive control ribavirin (EC50 = 1.3 mu M). BVDV is also considered to be a valuable surrogate for the hepatitis C virus (HCV) in antiviral drug studies. The above results provided a novel candidate for the development of anti-HCV agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.012

文献信息

• 3-Aryltetronic Acids: Efficient Preparation and Use as Precursors for Vulpinic Acids
  作者：Aurélie Mallinger、Thierry Le Gall、Charles Mioskowski

  DOI：10.1021/jo802038z

  日期：2009.2.6

  3-Aryltetronic acids were prepared in one step by treatment of a mixture of methyl arylacetates and methyl hydroxyacetates with potassium tert-butoxide, via tandem transesterification/Dieckmann condensation. Several mushroom or lichen pigments, vulpinic acids, were synthesized from 3-(4-methoxyphenyl)tetronic acid in three steps involving the reaction of the corresponding dianion with an α-ketoester

  通过串联酯交换反应/ Dieckmann缩合反应，用叔丁醇钾处理芳基乙酸甲酯和羟基乙酸甲酯的混合物，一步制得3-芳基酸。在三个步骤中，由3-（4-甲氧基苯基）tetronic酸合成了几种蘑菇或地衣颜料的硫化松香酸，这三个步骤涉及相应的二价阴离子与α-酮酸酯的反应以及所获得的叔醇的脱水成（E）的混合物-和（Z）-烯烃，它们在254nm的紫外线辐射下转化为天然（E）-异构体。樟脑酸，4,4'-二甲氧基硫代乙酸的合成，以及最近分离出的甲基3'，5'-dichloro-4,4'-di- O的首次合成因此，以有效的方式获得了苹果酸-草酸甲酯。
• One-Pot Synthesis of Tetronic Acids from Esters
  作者：Thierry Le Gall、Aurélie Mallinger、Charles Mioskowski

  DOI：10.1055/s-2008-1032061

  日期：2008.2

  Tetronic acids substituted by various groups were synthesized in one pot from the corresponding aryl- or heteroarylacetic acid esters and hydroxyacetic acid esters, by a tandem process involving a transesterification and a subsequent Dieckmann cyclization.

  通过涉及酯交换和随后的 Dieckmann 环化的串联方法，由相应的芳基-或杂芳基乙酸酯和羟基乙酸酯在一锅中合成被各种基团取代的 Tetronic 酸。