(5-Acetyl-1-benzofuran-6-yl) 1,3-benzodioxole-5-carboxylate | 862824-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (5-Acetyl-1-benzofuran-6-yl) 1,3-benzodioxole-5-carboxylate
• CAS: 862824-02-0
• 化学式: C₁₈H₁₂O₆
• 分子量: 324.29
• InChiKey: OEBZVPSNVCMAJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  75
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5-Acetyl-1-benzofuran-6-yl) 1,3-benzodioxole-5-carboxylate 在 吡啶 、 potassium tert-butylate 作用下， 生成 3-hydroxy-1-(6-hydroxybenzofuran-5-yl)-3-(3,4-methylenedioxy-phenyl)-propenone
  参考文献：
  名称：

  Amberlyst 15-Catalyzed Efficient Synthesis of 5-Acetyl-4-hydroxy-coumarone and 5-Acetyl-6-hydroxy-coumarone: Crucial Precursors for Several Naturally Occurring Furanoflavones

  摘要：

  本文描述了一种合成天然存在的呋喃黄酮和呋喃黄酮醌的新方法。角型和线型呋喃黄酮及呋喃黄酮醌仅需四个步骤即可合成，采用经济的试剂和简单的反应条件。我们方法的关键步骤是通过Amberlyst 15催化的苯氧基甲醛环化反应形成重要前体5-乙酰基-4-羟基香豆素和5-乙酰基-6-羟基香豆素。

  DOI：

  10.1055/s-2004-831180
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 吡啶 、 amberlyst-15 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.0h， 生成 (5-Acetyl-1-benzofuran-6-yl) 1,3-benzodioxole-5-carboxylate
  参考文献：
  名称：

  Amberlyst 15-Catalyzed Efficient Synthesis of 5-Acetyl-4-hydroxy-coumarone and 5-Acetyl-6-hydroxy-coumarone: Crucial Precursors for Several Naturally Occurring Furanoflavones

  摘要：

  本文描述了一种合成天然存在的呋喃黄酮和呋喃黄酮醌的新方法。角型和线型呋喃黄酮及呋喃黄酮醌仅需四个步骤即可合成，采用经济的试剂和简单的反应条件。我们方法的关键步骤是通过Amberlyst 15催化的苯氧基甲醛环化反应形成重要前体5-乙酰基-4-羟基香豆素和5-乙酰基-6-羟基香豆素。

  DOI：

  10.1055/s-2004-831180

文献信息

• Amberlyst 15-Catalyzed Efficient Synthesis of 5-Acetyl-4-hydroxy-coumarone and 5-Acetyl-6-hydroxy-coumarone: Crucial Precursors for Several Naturally Occurring Furanoflavones
  作者：Atul Goel、Manish Dixit

  DOI：10.1055/s-2004-831180

  日期：——

  A novel approach to the total synthesis of naturally occurring furanoflavones and furanochalcones is described. Angular and linear furanoflavones and furanochalcones have been prepared in just four steps, using economical reagents and simple reaction conditions. The key step of our approach is the formation of crucial precursors, 5-acetyl-4-hydroxy-coumarone and 5-acetyl-6-hydroxy-coumarone by Amberlyst 15-catalyzed cyclization of phen­oxyacetal.

  本文描述了一种合成天然存在的呋喃黄酮和呋喃黄酮醌的新方法。角型和线型呋喃黄酮及呋喃黄酮醌仅需四个步骤即可合成，采用经济的试剂和简单的反应条件。我们方法的关键步骤是通过Amberlyst 15催化的苯氧基甲醛环化反应形成重要前体5-乙酰基-4-羟基香豆素和5-乙酰基-6-羟基香豆素。
• Synthesis of functionalized acetophenones as protein tyrosine phosphatase 1B inhibitors
  作者：Manish Dixit、Brajendra K. Tripathi、Arvind K. Srivastava、Atul Goel

  DOI：10.1016/j.bmcl.2005.05.024

  日期：2005.7

  Protein tyrosine phosphatase 1B (PTP1B) is an enzyme that plays a critical role in down-regulating insulin signaling through dephosphorylation of the insulin receptor. Studies have shown that PTP1B knock-out mice showed increased insulin sensitivity in muscle and liver as well as resistance to obesity. A series of functionalized acetophenones were synthesized and evaluated for their PTP1B inhibitory activity. Some of the screened compounds displayed good inhibitory activity. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of benzofuran scaffold-based potential PTP-1B inhibitors
  作者：Manish Dixit、Brajendra K. Tripathi、Akhilesh K. Tamrakar、Arvind K. Srivastava、Brijesh Kumar、Atul Goel

  DOI：10.1016/j.bmc.2006.10.053

  日期：2007.1

  Protein tyrosine phosphatase 113 (PTP-1B) is an enzyme that plays a critical role in down-regulating insulin signaling through dephosphorylation of the insulin receptor. Studies have shown that PTP-1B knockout mice showed increased insulin sensitivity in muscle and liver as well as resistance to obesity. A series of hydroxy benzofuran methyl ketones and their naturally mimicking dimers and linear and angular furanochalcones and flavones have been evaluated as PTP-1B inhibitors. Screened compounds displayed good inhibitory activity. (c) 2006 Elsevier Ltd. All rights reserved.