(Z)-3-(p-nitrobenzylidene)-2-coumaranone | 118974-78-0

• 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: (Z)-3-(p-nitrobenzylidene)-2-coumaranone
• 英文别名: (3Z)-3-[(4-nitrophenyl)methylidene]-1-benzofuran-2-one
• CAS: 118974-78-0
• 化学式: C₁₅H₉NO₄
• 分子量: 267.241
• InChiKey: JPFUFIRNYRQZRL-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-(p-nitrobenzylidene)-2-coumaranone 在 盐酸 、 三乙胺 作用下， 以 苯 为溶剂， 反应 27.0h， 生成 (4'SR;5'RS) ethyl 4-(4-nitrophenyl)-5-(orthohydroxyphenyl)-3-phenyl-4,5-dihydroisoxazoline-5-carboxylate
  参考文献：
  名称：

  Spiroheterocycles from the Reaction of Arylnitrile Oxides with Some (Z)-3-Arylidene-2(3H)-benzofuranones. New Access to Orthohydroxyphenylisoxazoline Esters

  摘要：

  DOI：

  10.3987/com-06-10918
• 作为产物：
  描述：

  苯并呋喃-2(3H)-酮 、 对硝基苯甲醛 以 乙醇 为溶剂， 反应 96.0h， 生成 3-[1-(4-nitro-phenyl)-meth-(E)-ylidine]-3H-benzofuran-2-one 、 (Z)-3-(p-nitrobenzylidene)-2-coumaranone
  参考文献：
  名称：

  Remote Induction of the Condensation of p-Nitrobenzaldehyde on the Methylene Group of 5-Hydroxy-2-coumaranone

  摘要：

  DOI：

  10.3987/com-87-4447

文献信息

• Synthesis of New Spirocyclopropane and Oxadiazole Products
  作者：Amel Haouas、Naoufel Ben Hamadi[]、Moncef Msaddek

  DOI：10.1002/jhet.2249

  日期：2015.11

  In explorations of synthesis and chemistry of spiroheterocycles, we found that the reaction of 2‐diazopropane with arylidene‐benzofuran‐2(3H)‐one and arylidene‐benzofuran‐3(2H)‐one derivatives generated the spirocyclopropane products. In addition to the expected cycloadducts, an unexpected oxadiazole was formed in some cases. The structures of the obtained adducts have been assigned by means of spectroscopic

  在螺环杂环化合物的合成和化学研究中，我们发现2-重氮丙烷与亚芳基-苯并呋喃-2（3 H）-one和亚芳基-苯并呋喃-3（2 H）-one衍生物的反应生成了螺环丙烷产物。除预期的环加合物外，在某些情况下还会生成意外的恶二唑。所获得的加合物的结构已经通过光谱方法进行了分配。
• Design of novel dispirooxindolopyrrolidine and dispirooxindolopyrrolothiazole derivatives as potential antitubercular agents
  作者：Chourouk Mhiri、Sarra Boudriga、Moheddine Askri、Michael Knorr、Dharmarajan Sriram、Perumal Yogeeswari、Frédéric Nana、Christopher Golz、Carsten Strohmann

  DOI：10.1016/j.bmcl.2015.07.069

  日期：2015.10

  With the aim to develop new potent antitubercular agents, a series of novel dispirooxindolopyrrolidines and dispirooxindolopyrrolothiazoles have been synthesized via a three-component 1,3-dipolar cycloaddition of (Z)-3-arylidenebenzofuran-2-ones, substituted isatin derivatives and alpha-aminoacids. The stereochemistry of the spiroadducts has been confirmed by an X-ray diffraction analysis. All the target heterocycles were evaluated for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv strain and the most active compounds were subjected to cytotoxicity studies against (RAW 264.7) cell lines. Among them, twelve compounds showed potent anti-tubercular activity with MIC ranging from 1.56 to 6.25 mu g/mL. In particular dispirooxindolopyrrolothiazole derivatives 5c and 5f were found to be the most active (MIC of 1.56 mu g/mL) with a good safety profile (27.53% and 20.74% at 50 mu M, respectively). This is the first report demonstrating the benzofuranone oxindole hybrids as potential antimycobacterial agents. (C) 2015 Elsevier Ltd. All rights reserved.
• BARBIER, MICHEL, HETEROCYCLES, 27,(1988) N 4, C. 955-959
  作者：BARBIER, MICHEL

  DOI：——

  日期：——