γ-oxo-2-dibenzofuranbutanoic acid methyl ester | 36109-81-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: γ-oxo-2-dibenzofuranbutanoic acid methyl ester
• 英文别名: γ-oxo-2-dibenzofuranbutyric acid methyl ester；gamma-Oxo-2-dibenzofuranbutyric acid methyl ester；methyl 4-dibenzofuran-2-yl-4-oxobutanoate
• CAS: 36109-81-6
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: DMEMPCIVGDAJMG-UHFFFAOYSA-N

物化性质

• 沸点：
  458.5±25.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  γ-oxo-2-dibenzofuranbutanoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 生成 呋罗布芬
  参考文献：
  名称：

  Purification of .gamma.-oxo-2-dibenzofuranbutyric acid

  摘要：

  本发明揭示了从混合物中分离.gamma.-氧代-2-二苯基呋喃丁酸和.gamma.-氧代-3-二苯基呋喃丁酸的方法。这样的混合物是通过传统方法在弗里德尔-克拉夫茨反应中从二苯基呋喃和琥珀酸酐制备.gamma.-氧代-2-二苯基呋喃丁酸得到的。酸的混合物被转化为它们相应的较低烷基酯的混合物，该混合物通过重结晶或色谱分离成其组分烷基酯。对.gamma.-氧代-2-二苯基呋喃丁酸的较低烷基酯进行水解，得到所需的相应酸。

  公开号：

  US03985774A1
• 作为产物：
  描述：

  二苯并呋喃 、 丁二酸单甲酯酰氯 在 三氯化铝 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 反应 3.0h， 以94%的产率得到γ-oxo-2-dibenzofuranbutanoic acid methyl ester
  参考文献：
  名称：

  The Effect of 1,3-Diaryl-[1H]-pyrazole-4-acetamides on Glucose Utilization in ob/ob Mice

  摘要：

  This article provides evidence of a new class of compounds, 1,3-diaryl-[1H]-pyrazole-4-acetamides, initially identified from their ability to increase glucose transport in an adipocyte and muscle cell line and ultimately demonstrating dramatic glucose lowering in ob/ob Mice, a diabetic animal model. The lead compound, 1, possessed some behavioral-like effects which were removed by structural variation during the course of this investigation. Specifically, 11 g (RI = meta-CF3, Ar2 = 4 ' biphenyl, R3 = diethylamide) illustrated the potency of this series with ED50 values for glucose lowering in ob/ob mice of 3.0 mg/kg/day. Concomitant with its effect on glucose lowering, 11g also caused a 50% reduction in insulin levels consistent with an agent that increases whole body insulin sensitivity. 11g showed favorable pharmacokinetic data with acceptable absorption, negligible metabolism, and good duration of action. 11g demonstrated no appreciable adipogenic effect through PPAR gamma agonism, a characteristic of the thiazolidinediones (TZD), and so represents a potentially new class of agents for the treatment of diabetes.

  DOI：

  10.1021/jm010032c

文献信息

• US3985774A
  申请人：——

  公开号：US3985774A

  公开（公告）日：1976-10-12
• The Effect of 1,3-Diaryl-[1H]-pyrazole-4-acetamides on Glucose Utilization in ob/ob Mice
  作者：Gregory R. Bebernitz、Greg Argentieri、Beverly Battle、Christine Brennan、Bork Balkan、Bryan F. Burkey、Michele Eckhardt、Jiaping Gao、Prasad Kapa、Robert J. Strohschein、Herbert F. Schuster、Mary Wilson、David D. Xu

  DOI：10.1021/jm010032c

  日期：2001.8.1

  This article provides evidence of a new class of compounds, 1,3-diaryl-[1H]-pyrazole-4-acetamides, initially identified from their ability to increase glucose transport in an adipocyte and muscle cell line and ultimately demonstrating dramatic glucose lowering in ob/ob Mice, a diabetic animal model. The lead compound, 1, possessed some behavioral-like effects which were removed by structural variation during the course of this investigation. Specifically, 11 g (RI = meta-CF3, Ar2 = 4 ' biphenyl, R3 = diethylamide) illustrated the potency of this series with ED50 values for glucose lowering in ob/ob mice of 3.0 mg/kg/day. Concomitant with its effect on glucose lowering, 11g also caused a 50% reduction in insulin levels consistent with an agent that increases whole body insulin sensitivity. 11g showed favorable pharmacokinetic data with acceptable absorption, negligible metabolism, and good duration of action. 11g demonstrated no appreciable adipogenic effect through PPAR gamma agonism, a characteristic of the thiazolidinediones (TZD), and so represents a potentially new class of agents for the treatment of diabetes.
• Purification of .gamma.-oxo-2-dibenzofuranbutyric acid
  申请人：American Home Products Corporation

  公开号：US03985774A1

  公开（公告）日：1976-10-12

  A process for the separation of .gamma.-oxo-2-dibenzofuranbutyric acid from a mixture of said acid and .gamma.-oxo-3-dibenzofuranbutyric acid is disclosed. Such a mixture is obtained by the prior art method of preparing .gamma.-oxo-2-dibenzofuranbutyric acid from dibenzofuran and succinic anhydride in a Friedel-Crafts reaction. The mixture of acids is converted to a mixture of their corresponding lower alkyl esters which is separated by recrystallization or chromatography into its component alkyl esters. Hydrolysis of the lower alkyl ester of .gamma.-oxo-2-dibenzofuranbutyric acid gives the desired corresponding acid.

  本发明揭示了一种从混合物中分离γ-氧代-2-二苯并呋喃丁酸和γ-氧代-3-二苯并呋喃丁酸的方法。这样的混合物是通过传统方法在Friedel-Crafts反应中从二苯并呋喃和琥珀酸酐制备γ-氧代-2-二苯并呋喃丁酸而得。这些酸的混合物被转化为它们相应的较低烷基酯混合物，该混合物通过重结晶或色谱法分离成其组分烷基酯。γ-氧代-2-二苯并呋喃丁酸的较低烷基酯水解产生所需的相应酸。