7-methylbenzofuran-2-carboxylic acid | 17349-64-3

• 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: 7-methylbenzofuran-2-carboxylic acid
• 英文别名: 7-Methyl-benzofuran-2-carbonsaeure；7-Methyl-1-benzofuran-2-carboxylic acid
• CAS: 17349-64-3
• 化学式: C₁₀H₈O₃
• 分子量: 176.172
• InChiKey: ZGVCUDGNUWNJDI-UHFFFAOYSA-N

物化性质

• 沸点：
  327.7±22.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  7-methylbenzofuran-2-carboxylic acid 在 sodium amalgam 、 氯化亚砜 、 氨 作用下， 以 1,4-二氧六环 、 sodium hydroxide 、 苯 为溶剂， 反应 7.0h， 生成 7-methyl-2,3-dihydro-1-benzofuran-2-carboxamide
  参考文献：
  名称：

  .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity

  摘要：

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.

  DOI：

  10.1021/jm00371a003
• 作为产物：
  描述：

  ethyl 7-methylbenzofuran-2-carboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.75h， 生成 7-methylbenzofuran-2-carboxylic acid
  参考文献：
  名称：

  .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity

  摘要：

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.

  DOI：

  10.1021/jm00371a003

文献信息

• [EN] TROPANE COMPOUNDS<br/>[FR] COMPOSÉS DE TROPANE
  申请人：EXELIXIS INC

  公开号：WO2009055077A1

  公开（公告）日：2009-04-30

  A compound according to Formula I or II: (I) or (II) wherein R1, R1b, R2, L1, and L2 and L2b are as defined in the specification, pharmaceutical compositions thereof, and methods of use thereof.

  根据公式I或II的化合物：（I）或（II），其中R1、R1b、R2、L1和L2以及L2b的定义如规范中所述，以及其药物组合物和使用方法。
• Modulation on C- and N-Terminal Moieties of a Series of Potent and Selective Linear Tachykinin NK₂Receptor Antagonists
  作者：Martina Gensini、Maria Altamura、Tula Dimoulas、Valentina Fedi、Danilo Giannotti、Sandro Giuliani、Antonio Guidi、Nicholas J. S. Harmat、Stefania Meini、Rossano Nannicini、Franco Pasqui、Manuela Tramontana、Antonio Triolo、Carlo Alberto Maggi

  DOI：10.1002/cmdc.200900389

  日期：2010.1.4

  Herein we describe the synthesis of a series of new potent tachykinin NK2 receptor antagonists by the modulation of the C‐ and N‐terminal moieties of ibodutant (MEN 15596, 1). The N‐terminal benzo[b]thiophene ring was replaced by different substituted naphthalenes and benzofurans, while further modifications were evaluated at the C‐terminal tetrahydropyran moiety. Most compounds demonstrated a high affinity

  本文中，我们描述了一系列新的有效速激肽NK的合成2通过ibodutant的C-和N-末端部分的调制（MEN 15596，受体拮抗剂1）。N末端的苯并[ b ]噻吩环被不同的取代萘和苯并呋喃取代，同时在C末端的四氢吡喃部分评估了进一步的修饰。大多数化合物表现出对人NK 2受体的高亲和力和体外拮抗剂的高效力，表明可以在分子的两个末端引入广泛的取代基，而不会影响与NK 2受体的相互作用。对选定的化合物进行了体内测试，证实了其作为NK的活性2个拮抗剂。特别是，对豚鼠静脉内和静脉内给药后，化合物61b能够拮抗NK 2诱导的结肠收缩，其作用力和作用持续时间与参考化合物1（MEN 15596，ibodutant）完全相同。
• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSES ORGANIQUES
  申请人：SPEEDEL EXPERIMENTA AG

  公开号：WO2005061457A1

  公开（公告）日：2005-07-07

  Novel substituted piperidines of the general formulae (I) and (II) with the substituent definitions as explained in detail in the description are described. The compounds are suitable in particular as renin inhibitors and are highly potent.

  描述了一种具有一般式(I)和(II)的新型替代哌啶化合物，其中详细说明了取代基定义。这些化合物特别适用作为肾素抑制剂，并且具有很高的效力。
• 硼酸类化合物及其制备方法和用途
  申请人：复旦大学

  公开号：CN107151255A

  公开（公告）日：2017-09-12

  本发明涉及药物化学和药物治疗学领域。具体涉及新的硼酸类化合物及其制备方法和用途，尤其涉及新的取代五元杂环硼酸类及取代苯并五元杂环硼酸类化合物及其制备方法，本发明制得的如下式结构的取代五元杂环硼酸类及取代苯并五元杂环硼酸类化合物经生物活性筛选试验，结果表明，所述的化合物具有抑制蛋白酶体的功能，可进一步用于制备治疗与蛋白酶体相关疾病的药物。
• Tandem Synthesis of 2-Carboxybenzofurans <i>via</i> Sequential Cu-Catalyzed C–O Coupling and Mo(CO)₆-Mediated Carbonylation Reactions
  作者：Qinliang Mo、Nan Sun、Liqun Jin、Baoxiang Hu、Zhenlu Shen、Xinquan Hu

  DOI：10.1021/acs.joc.0c01620

  日期：2020.9.4

  A modular tandem synthesis of 2-carboxybenzofurans from 2-gem-dibromovinylphenols has been established based on a sequence of Cu-catalyzed intramolecular C–O coupling and Mo(CO)6-mediated intermolecular carbonylation reactions. This protocol allowed one-step access to a broad variety of functionalized benzofuran-2-carboxylic acids, esters, and amides in good to excellent yields under Pd- and CO gas-free

  由2- 2-羧基苯并呋喃的模块化串联合成宝石-dibromovinylphenols已经基于Cu催化的分子内CO耦合和Mo（CO）的序列被建立6个介导的分子间羰基化反应。该方案允许在无Pd和CO气体条件下以良好至极佳的收率一步一步获得各种官能化的苯并呋喃-2-羧酸，酯和酰胺。