benzofuran-3-yl-oxo-acetic acid | 186317-65-7

• 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: benzofuran-3-yl-oxo-acetic acid
• 英文别名: benzofuran-3-yl-glyoxylic acid；Benzofuran-3-yl-glyoxylsaeure；2-(1-Benzofuran-3-yl)-2-oxoacetic acid
• CAS: 186317-65-7
• 化学式: C₁₀H₆O₄
• 分子量: 190.155
• InChiKey: SNLJYBAQFBAFQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzofuran-3-yl-oxo-acetic acid 以 四氢呋喃 为溶剂， 生成 2-Benzofuran-3-yl-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-2-oxo-acetamide
  参考文献：
  名称：

  Isosteric replacement of the indole nucleus by benzothiophene and benzofuran in a series of indolylglyoxylylamine derivatives with partial agonist activity at the benzodiazepine receptor

  摘要：

  A number of benzothienyl- and benzofurylglyoxylylamine derivatives, which are analogues of previously described indolylglyoxylylamines with a partial agonist activity, are reported in this paper. They were synthesized and tested to verify the importance of the presence of the indole NH group in the interaction of this class of compounds with the benzodiazepine agonist receptor site, since it was reported in literature that a hydrogen bond donor group such as NH was not necessary to elicit an agonist response. Several thienylglyoxylylamine derivatives were also prepared and tested. None of the compounds showed a high affinity at the BzR, demonstrating that the indole NH plays a decisive role in the interaction of the agonist glyoxylylamine ligands with the receptor site.

  DOI：

  10.1016/s0223-5234(97)86173-9
• 作为产物：
  描述：

  (2-carboxymethoxy-phenyl)-glyoxylic acid 在 吡啶 、 盐酸 、 氢氧化钾 、 氯化亚砜 、 乙醚 、 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 生成 benzofuran-3-yl-oxo-acetic acid
  参考文献：
  名称：

  合成香豆酮-3-羰基合成酯和合成香豆酰基-3-乙酰基合成

  摘要：

  DOI：

  10.1002/hlca.193702001127

文献信息

• Benzofurans as Efficient Dienophiles in Normal Electron Demand [4 + 2] Cycloadditions
  作者：Nathalie Chopin、Hélène Gérard、Isabelle Chataigner、Serge R. Piettre

  DOI：10.1021/jo802205d

  日期：2009.2.6

  arising from the reaction have been shown to depend on different factors among which the type of the electron-withdrawing substituent of the benzofuran, the nature of the reacting diene, and the method of activation. In the presence of all-carbon dienes, the reaction yields the expected Diels−Alder adducts. When thermal activation is insufficient, a biactivation associating zinc chloride catalysis and

  贫电子的苯并呋喃的脱芳香化作用可能是通过芳香族的2,3-碳-碳双键作为亲二烯体参与正常的电子需求[4 + 2]环加成反应而实现的。由此产生的三环杂环在顺式环结处具有季中心，这是许多生物碱如吗啡，加兰他敏或卢纳丁的特征。已经表明，由反应产生的产物取决于不同的因素，其中包括苯并呋喃的吸电子取代基的类型，反应中的二烯的性质以及活化方法。在全碳二烯存在下，反应生成预期的Diels-Alder加合物。当热活化不足时，例如，当环己二烯参与该方法时，需要双活化使氯化锌催化和高压缔合以产生高收率和高立体选择性的环加合物。使用更多官能化的二烯，例如带有烷氧基或甲硅烷基氧基取代基的二烯，也显示出热活化的极限，在这种情况下，高压条件是非常合适的。Danishefsky的二烯的参与引发了反应位点的竞争。芳香族的2,3-碳-碳双键无疑是最具反应性的亲二烯体，而3-羰基单元成为与苯并呋喃具有竞争性的竞争性反应位点，尤
• INDOLE, AZAINDOLE AND RELATED HETEROCYCLIC AMIDOPIPERAZINE DERIVATIVES
  申请人：Bristol-Myers Squibb Company

  公开号：EP1381366B1

  公开（公告）日：2009-04-22
• Isosteric replacement of the indole nucleus by benzothiophene and benzofuran in a series of indolylglyoxylylamine derivatives with partial agonist activity at the benzodiazepine receptor
  作者：F Da Settimo、A Lucacchini、AM Marini、C Martini、G Primofiore、G Senatore、S Taliani

  DOI：10.1016/s0223-5234(97)86173-9

  日期：1996.1

  A number of benzothienyl- and benzofurylglyoxylylamine derivatives, which are analogues of previously described indolylglyoxylylamines with a partial agonist activity, are reported in this paper. They were synthesized and tested to verify the importance of the presence of the indole NH group in the interaction of this class of compounds with the benzodiazepine agonist receptor site, since it was reported in literature that a hydrogen bond donor group such as NH was not necessary to elicit an agonist response. Several thienylglyoxylylamine derivatives were also prepared and tested. None of the compounds showed a high affinity at the BzR, demonstrating that the indole NH plays a decisive role in the interaction of the agonist glyoxylylamine ligands with the receptor site.
• Synthèse de l'acide coumarone-3-carbonique et de l'acide coumaronyl-3-acétique
  作者：Valentine Titoff、H. Müller、T. Reichstein

  DOI：10.1002/hlca.193702001127

  日期：——