6-nitro-2-acetyl-7-hydroxybenzofuran | 83767-25-3

• 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: 6-nitro-2-acetyl-7-hydroxybenzofuran
• 英文别名: 1-(7-Hydroxy-6-nitro-1-benzofuran-2-yl)ethanone
• CAS: 83767-25-3
• 化学式: C₁₀H₇NO₅
• 分子量: 221.169
• InChiKey: QDPZBQLZXJZHRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 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：
  96.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-乙酰基-7-甲氧基苯并呋喃 在 Chlorure de pyridinium anhydre 、 硝酸 作用下， 以 乙酸酐 为溶剂， 反应 0.77h， 生成 6-nitro-2-acetyl-7-hydroxybenzofuran
  参考文献：
  名称：

  Bachelet, Jean-Pierre; Clavel, Jean-Marc; Demerseman, Pierre, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 737 - 739

  摘要：

  DOI：

文献信息

• Antibacterial activity and polarographic half-wave reduction potential of 2-nitrobenzo(b)furans.
  作者：YOSHITAKA OHISHI、KIYOSHI KURIYAMA、YOSHIO DOI、TERUO NAKANISHI

  DOI：10.1248/cpb.33.2854

  日期：——

  The antibacterial activities of a series of 2-nitrobenzo [b] furan derivatives against St. aureus, B. subtilis, E. coli, Sal. typhimurium, Sal. enteritidis, Sh. flexneri, Pr. vulgaris or Ps. aeruginosa were determined in vitro. Most of the compounds showed considerable activities against the bacteria except Pr. vulgaris and Ps. aeruginosa and one of them was about 30 times as active as nitrofurantoin against St. aureus. Mono- and dimethoxy derivatives (2a, 3a, 4a, 5f) were the most active. The polarographic half-wave potentials (E1/2) of the 2-nitrobenzo [b] furans at pH 7 were in a narrow range of -0.450±0.04 V, whereas the E1/2 values of regioisomeric nitrobenzo [b] furans were more negative (-0.560--0.726 V). In the case of 2-nitrobenzo [b] furans, substituent (s) on the benzene ring had little influence on the reduction potential of the 2-nitro group, whereas the antibacterial activity depended markedly on the substituent group (s).

  一系列2-硝基苯并[b]呋喃衍生物对金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌、鼠伤寒沙门氏菌、肠炎沙门氏菌、弗氏志贺菌、普通变形杆菌或铜绿假单胞菌的抗菌活性在体外被测定。大多数化合物对这些细菌显示出显著的活性，除了普通变形杆菌和铜绿假单胞菌，它们中的一种对金黄色葡萄球菌的活性大约是呋喃西林的30倍。单甲氧基和二甲氧基衍生物（2a, 3a, 4a, 5f）最为活跃。在pH 7时，2-硝基苯并[b]呋喃的极谱半波电位（E1/2）在一个狭窄的范围内，为-0.450±0.04 V，而区域异构的硝基苯并[b]呋喃的E1/2值更为负（-0.560至-0.726 V）。对于2-硝基苯并[b]呋喃来说，苯环上的取代基对2-硝基基团的还原电位几乎没有影响，然而抗菌活性明显取决于取代基团。
• Bachelet, Jean-Pierre; Clavel, Jean-Marc; Demerseman, Pierre, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 737 - 739
  作者：Bachelet, Jean-Pierre、Clavel, Jean-Marc、Demerseman, Pierre、Royer, Rene

  DOI：——

  日期：——