1-(1-Benzofuran-2-yl)-3-(2-nitrophenyl)prop-2-en-1-one | 849510-79-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(1-Benzofuran-2-yl)-3-(2-nitrophenyl)prop-2-en-1-one
• CAS: 849510-79-8
• 化学式: C₁₇H₁₁NO₄
• 分子量: 293.279
• InChiKey: SGGACKIJMACUOK-UHFFFAOYSA-N

物化性质

• 熔点：
  136-139 °C
• 沸点：
  481.1±45.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1-Benzofuran-2-yl)-3-(2-nitrophenyl)prop-2-en-1-one 在 ammonium hydroxide 、 二氢吡啶 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以75%的产率得到(3-amino-1H-indol-2-yl)(benzofuran-2-yl)methanone
  参考文献：
  名称：

  由2-硝基查耳酮和氨或伯胺合成3-氨基吲哚

  摘要：

  在无过渡金属的条件下，实现了以氨或伯胺为“ N”源的3-氨基吲哚合成的分步经济策略。获得了一系列3-氨基吲哚，其中含有丰富的“ N”源，具有高效率，温和的条件，环境友好性和可扩展性。通过这种新开发的策略，成功完成了COX-2抑制剂和微管蛋白聚合抑制剂中间体的高效合成。

  DOI：

  10.1002/adsc.201900551
• 作为产物：
  描述：

  2-乙酰基苯并呋喃 、 邻硝基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 130.0 ℃ 、1.0 MPa 条件下， 反应 0.17h， 生成 1-(1-Benzofuran-2-yl)-3-(2-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis, and antitubercular evaluation of novel series of 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs

  摘要：

  Twenty-eight newer 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs were synthesized by microwave irradiation method and evaluated for in-vitro and in-vivo antitubercular activity against multidrug-resistant M. tuberculosis stains. Structure activity relationship study was carried out and found NO2 (o) substituted 3-benzo-furan-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin was most potent antitubercular agent against M. tuberculosis, even better than standard drug isoniazid and comparable with rifampin. Other synthesized compounds 7j, 7f, 7a, 7e and 5d, 5f were found moderate to good activity in in-vitro model at lower IC50 values 85 mu M, 154 mu M, 157 mu M, 164 mu M, 170 mu M and 190 mu ML respectively. In in-vivo animal model compound 7j was drastically reduced the bacterial load in lung and spleen tissues at the dose of 25 mg/kg body weight. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.035

文献信息

• Cobalt Nickel Bimetallic Nanocatalyst Supported on g‐C₃N₄ for Selective Hydrogenation of <i>α,β‐</i>Unsaturated Carbonyls and Nitroarenes
  作者：Vijay Tripathi、Panyala Linga Reddy、Pankaj E. Hande、Dharmendra S. Vishwakarma、Dipak J. Fartade、Leela S. Panchakarla、Santosh J. Gharpure

  DOI：10.1002/cctc.202300460

  日期：2023.8.7

  Chemoselective hydrogenation of the α,β-unsaturated carbonyls and nitroarene using CoNi@g-C3N4 bimetallic nanocatalyst.

  使用CoNi@gC 3 N 4双金属纳米催化剂对α,β-不饱和羰基和硝基芳烃进行化学选择性氢化。
• Design, synthesis, and antitubercular evaluation of novel series of 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs
  作者：Kuntal Manna、Yadvendra K. Agrawal

  DOI：10.1016/j.ejmech.2010.05.035

  日期：2010.9

  Twenty-eight newer 3-benzofuran-5-aryl-1-pyrazolyl-pyridylmethanone and 3-benzofuran-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin analogs were synthesized by microwave irradiation method and evaluated for in-vitro and in-vivo antitubercular activity against multidrug-resistant M. tuberculosis stains. Structure activity relationship study was carried out and found NO2 (o) substituted 3-benzo-furan-5-aryl-1-pyrazolylcarbonyl-4-oxo-naphthyridin was most potent antitubercular agent against M. tuberculosis, even better than standard drug isoniazid and comparable with rifampin. Other synthesized compounds 7j, 7f, 7a, 7e and 5d, 5f were found moderate to good activity in in-vitro model at lower IC50 values 85 mu M, 154 mu M, 157 mu M, 164 mu M, 170 mu M and 190 mu ML respectively. In in-vivo animal model compound 7j was drastically reduced the bacterial load in lung and spleen tissues at the dose of 25 mg/kg body weight. (C) 2010 Elsevier Masson SAS. All rights reserved.
• 3‐Aminoindole Synthesis from 2‐Nitrochalcones and Ammonia or Primary Amines
  作者：Guan Zhang、Lu Lin、Kai Yang、Shihui Wang、Qiang Feng、Jun Zhu、Qiuling Song

  DOI：10.1002/adsc.201900551

  日期：2019.8.21

  A step‐economic strategy for 3‐aminoindoles synthesis with ammonia or primary amines as “N” source under transition‐metal‐free conditions was achieved. A series of 3‐aminoindoles was obtained with abundant “N” source featuring high efficiency, mild conditions, environmental friendliness and scalability. Efficient syntheses of the intermediates of COX‐2 inhibitor and tubulin polymerization inhibitor

  在无过渡金属的条件下，实现了以氨或伯胺为“ N”源的3-氨基吲哚合成的分步经济策略。获得了一系列3-氨基吲哚，其中含有丰富的“ N”源，具有高效率，温和的条件，环境友好性和可扩展性。通过这种新开发的策略，成功完成了COX-2抑制剂和微管蛋白聚合抑制剂中间体的高效合成。