3-chloro-4-(4'-methylsulfonylphenyl)-5H-furan-2-one | 487047-31-4

• 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: 3-chloro-4-(4'-methylsulfonylphenyl)-5H-furan-2-one
• 英文别名: 2-chloro-3-(4-methanesulfonyl-phenyl)-2-buten-4-olide；4-chloro-3-(4-methylsulfonylphenyl)-2H-furan-5-one
• CAS: 487047-31-4
• 化学式: C₁₁H₉ClO₄S
• 分子量: 272.709
• InChiKey: MLVMRENYWBZNRK-UHFFFAOYSA-N

物化性质

• 沸点：
  525.4±50.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 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：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-4-(4'-methylsulfonylphenyl)-5H-furan-2-one 、 苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 苄基三乙基氯化铵 cesium fluoride 作用下， 以 水 、 甲苯 为溶剂， 反应 7.0h， 以74%的产率得到罗非昔布
  参考文献：
  名称：

  Preparation of aryl-substituted butenolides using mucohalic acids

  摘要：

  制备3-芳基-2-丁烯-4-内酯和2,3-双芳基-2-丁烯-4-内酯的方法和材料被公开。这些方法包括将粘酸与还原剂反应以得到2,3-二卤代-2-丁烯-4-内酯，该卤代物至少与一种芳基硼酸进行钯催化的交叉偶联反应。

  公开号：

  US20050131239A1
• 作为产物：
  描述：

  4-甲硫基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride Oxone 、 苄基三乙基氯化铵 、 cesium fluoride 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 72.0h， 生成 3-chloro-4-(4'-methylsulfonylphenyl)-5H-furan-2-one
  参考文献：
  名称：

  Reinvestigation of Mucohalic Acids, Versatile and Useful Building Blocks for Highly Functionalized α,β-Unsaturated γ-Butyrolactones

  摘要：

  [GRAPHICS]Mucohalic acids (mucochloric acid (1, 3,4-dichloro-5-hydroxy-5H-furan-2-one) and mucobromic acid (2, 3,4-dibromo-5-hydroxy-5H-furan-2-one)) are inexpensive, commercially available starting materials with multiple functional groups. These compounds have been modified by way of reduction followed by Suzuki cross-coupling reactions involving arylboronic acids to afford highly functionalized alpha,beta-unsaturated gamma-butyrolactones in excellent yield. The synthetic utility of these building blocks was effectively demonstrated through preparation of the antiinflammatory drug Vioxx.

  DOI：

  10.1021/ol027122b

文献信息

• Preparation of aryl-substituted butenolides using mucohalic acids
  申请人：Blazecka Garth Peter

  公开号：US20050131239A1

  公开（公告）日：2005-06-16

  Methods and materials for preparing 3-aryl-2-buten-4-olides and 2,3-bisaryl-2-buten-4-olides are disclosed. The methods include reacting a mucohalic acid with a reducing agent to give a 2,3-dihalo-2-buten-4-olide, which undergoes at least one Pd catalyzed cross-coupling reaction with an arylboronic acid.

  制备3-芳基-2-丁烯-4-内酯和2,3-双芳基-2-丁烯-4-内酯的方法和材料被公开。这些方法包括将粘酸与还原剂反应以得到2,3-二卤代-2-丁烯-4-内酯，该卤代物至少与一种芳基硼酸进行钯催化的交叉偶联反应。
• Reinvestigation of Mucohalic Acids, Versatile and Useful Building Blocks for Highly Functionalized α,β-Unsaturated γ-Butyrolactones
  作者：Ji Zhang、Peter G. Blazecka、Daniel Belmont、James G. Davidson

  DOI：10.1021/ol027122b

  日期：2002.12.1

  [GRAPHICS]Mucohalic acids (mucochloric acid (1, 3,4-dichloro-5-hydroxy-5H-furan-2-one) and mucobromic acid (2, 3,4-dibromo-5-hydroxy-5H-furan-2-one)) are inexpensive, commercially available starting materials with multiple functional groups. These compounds have been modified by way of reduction followed by Suzuki cross-coupling reactions involving arylboronic acids to afford highly functionalized alpha,beta-unsaturated gamma-butyrolactones in excellent yield. The synthetic utility of these building blocks was effectively demonstrated through preparation of the antiinflammatory drug Vioxx.