2-ethylbenzofuran-3-carboxylic acid | 52489-34-6

• 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: 2-ethylbenzofuran-3-carboxylic acid
• 英文别名: 2-ethyl-benzofuran-3-carboxylic acid；2-Aethyl-benzofuran-3-carbonsaeure；2-Aethyl-benzofuran-carbonsaeure-(3)；2-Aethyl-cumaron-carbonsaeure-(3)；2-Ethyl-1-benzofuran-3-carboxylic acid
• CAS: 52489-34-6
• 化学式: C₁₁H₁₀O₃
• mdl: MFCD17257563
• 分子量: 190.199
• InChiKey: TUGDACOXNMKOOC-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  327.5±22.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethylbenzofuran-3-carboxylic acid 在 五氯化磷 作用下， 生成 2-ethylbenzofuran-3-carboxylic acid chloride
  参考文献：
  名称：

  Royer,R.; Bisagni,E., Bulletin de la Societe Chimique de France, 1963, p. 1746 - 1752

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙基-3-乙酰基苯并呋喃 在 alkaline aqueous sodium hypobromite solution 作用下， 生成 2-ethylbenzofuran-3-carboxylic acid
  参考文献：
  名称：

  Bisagni et al., Journal of the Chemical Society, 1955, p. 3688,3692

  摘要：

  DOI：

文献信息

• Construction of Benzofuran-3(2<i>H</i>)-one Scaffolds with a Quaternary Center via Rh/Co Relay Catalyzed C–H Functionalization/Annulation of <i>N</i>-Aryloxyacetamides and Propiolic Acids
  作者：Wen-Kui Yuan、Ming-Hui Zhu、Rui-Sen Geng、Guang-Yi Ren、Lin-Bao Zhang、Li-Rong Wen、Ming Li

  DOI：10.1021/acs.orglett.9b00181

  日期：2019.3.15

  An unprecedented synthesis of valuable benzofuran-3(2H)-one scaffolds with a quaternary center was developed via Rh/Co relay catalyzed C–H functionalization/annulation of N-aryloxyacetamides with propiolic acids in moderate to good yields. The reaction features the simultaneous construction of the benzofuran motif containing a C2 quaternary center and a C3 carbonyl group. The preliminary mechanism

  通过Rh / Co中继催化N-芳氧基乙酰胺与丙酸的C–H官能化/环化，中等至良好的产率，开发了具有四元中心的有价值的苯并呋喃3（2 H）-1骨架的空前合成。该反应的特征在于同时构建含有C 2季中心和C 3羰基的苯并呋喃基序。初步机理研究证明，C3羰基的O原子起源于分子氧。
• 6-(Aryl-amido or aryl-amidomethyl)-naphthalen-2-yloxy-acidic derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1)
  申请人：Wyeth

  公开号：US20030045560A1

  公开（公告）日：2003-03-06

  This invention provides novel compounds, pharmaceutical compositions and methods of treating thrombotic disorders in mammals, the compounds having the formula: 1 Wherein: Ar is phenyl, naphthyl, furanyl, benzofuranyl, indolyl, pyrazolyl, oxazolyl, fluorenyl, phenylcycloalkane where the cycloalkane can be cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl and Ar can be optionally substituted by 1 to 3 groups selected from C 1 -C 6 alkyl, C 1 -C 6 alkoxy, hydroxy, phenyl-(CH 2 ) 0-6 —, phenyl-(CH 2 ) 0-6 O—, C 3 -C 6 cycloalkyl, —(CH 2 )—C 3 -C 6 cycloalkyl, halogen, C 1 -C 3 perflouroalkyl and C 1 -C 3 perfluoroalkoxy where phenyl can be substituted with from 1 to 3 groups selected from C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenyl, halogen, trifluoromethyl or trifluoromethoxy; R 1 is hydrogen, C 1 -C 6 alkyl or phenyl-(CH 2 ) 1-6 — where phenyl can be substituted with C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo, trifluoromethyl or trifluoromethoxy; R 2 and R 3 are H, C 1 -C 6 alkyl, phenyl-(CH 2 ) 0-3 —, halo and C 1 -C 3 perfluoroalkyl where phenyl can be substituted with C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo, trifluoromethyl or trifluoromethoxy; R 4 is —CHR 5 CO 2 H or —CH 2 -tetrazole where R 5 is H or benzyl; and n=0 or 1; or a pharmaceutically acceptable salt or ester form thereof.

  这项发明提供了新颖的化合物、药物组合物和治疗哺乳动物血栓性疾病的方法，这些化合物具有以下结构式：1其中：Ar为苯基、萘基、呋喃基、苯并呋喃基、吲哚基、吡唑基、噁唑基、芴基、苯基环烷烃，其中环烷烃可以是环丙基、环丁基、环戊基或环己基，Ar可以选择性地被1至3个来自C1-C6烷基、C1-C6烷氧基、羟基、苯基-(CH2)0-6—、苯基-(CH2)0-6O—、C3-C6环烷基、—(CH2)—C3-C6环烷基、卤素、C1-C3全氟烷基和C1-C3全氟烷氧基的基团取代；R1为氢、C1-C6烷基或苯基-(CH2)1-6—，其中苯基可以被C1-C6烷基、C1-C6烷氧基、卤素、三氟甲基或三氟甲氧基取代；R2和R3为H、C1-C6烷基、苯基-(CH2)0-3—、卤素和C1-C3全氟烷基，其中苯基可以被C1-C6烷基、C1-C6烷氧基、卤素、三氟甲基或三氟甲氧基取代；R4为—CHR5CO2H或—CH2-四唑基，其中R5为H或苄基；n=0或1；或其药用可接受的盐或酯形式。
• Encoded Library Technology as a Source of Hits for the Discovery and Lead Optimization of a Potent and Selective Class of Bactericidal Direct Inhibitors of <i>Mycobacterium tuberculosis</i> InhA
  作者：Lourdes Encinas、Heather O’Keefe、Margarete Neu、Modesto J. Remuiñán、Amish M. Patel、Ana Guardia、Christopher P. Davie、Natalia Pérez-Macías、Hongfang Yang、Maire A. Convery、Jeff A. Messer、Esther Pérez-Herrán、Paolo A. Centrella、Daniel Álvarez-Gómez、Matthew A. Clark、Sophie Huss、Gary K. O’Donovan、Fátima Ortega-Muro、William McDowell、Pablo Castañeda、Christopher C. Arico-Muendel、Stane Pajk、Joaquín Rullás、Iñigo Angulo-Barturen、Emilio Álvarez-Ruíz、Alfonso Mendoza-Losana、Lluís Ballell Pages、Julia Castro-Pichel、Ghotas Evindar

  DOI：10.1021/jm401326j

  日期：2014.2.27

  Tuberculosis (TB) is one of the world's oldest and deadliest diseases, killing a person every 20 s. InhA, the enoyl-ACP reductase from Mycobacterium tuberculosis, is the target of the frontline antitubercular drug isoniazid (INH). Compounds that directly target InhA and do not require activation by mycobacterial catalase peroxidase KatG are promising candidates for treating infections caused by INH resistant strains. The application of the encoded library technology (ELT) to the discovery of direct InhA inhibitors yielded compound 7 endowed with good enzymatic potency but with low antitubercular potency. This work reports the hit identification, the selected strategy for potency optimization, the structure-activity relationships of a hundred analogues synthesized, and the results of the in vivo efficacy studies performed with the lead compound 65.
• Chatterjea, Journal of the Indian Chemical Society, 1957, vol. 34, p. 299,304
  作者：Chatterjea

  DOI：——

  日期：——
• Methods for the homologation of benzofurancarboxylic acids using dianionic intermediates
  作者：Cheryl D. Buttery、David W. Knight、Andrew P. Nott

  DOI：10.1016/s0040-4039(00)88366-5

  日期：1982.1