2-hydroxy-2-(3-methylbut-2-enyl)-2H-indene-1,3-dione | 145046-46-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-hydroxy-2-(3-methylbut-2-enyl)-2H-indene-1,3-dione
• 英文别名: 2-hydroxy-2-(3-methylbut-2-enyl)indene-1,3-dione
• CAS: 145046-46-4
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: FDIGUUCEGIFTHD-UHFFFAOYSA-N

物化性质

• 沸点：
  388.4±42.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  黄钟花醌 在 氧气 、 cobalt(II) diacetate tetrahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以20%的产率得到2-hydroxy-2-(3-methylbut-2-enyl)-2H-indene-1,3-dione
  参考文献：
  名称：

  Cobalt mediated ring contraction reaction of lapachol and initial antibacterial evaluation of naphthoquinones derived from lapachol

  摘要：

  The synthesis of 2-hydroxy-2-(3-methylbut-2-enyl)-2H-indene-1,3-dione 3, from lapachol which involves a ring contraction via the Hooker intermediate 1,2-dihydroxy-2-(3-methylbut-2-en-1-yl)-3-oxo-2,3-dihydro-1H-indene-1-carboxylic acid 2 is described. Different pyranonaphthoquinone derivatives, obtained in our previous synthetic work, were screened for antimycobacterial (Mycobacterium tuberculosis) activity and against resistant strains of Gram-positive (Bacillus cereus and Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. The results indicated significant activity of all the tested samples against M. tuberculosis and only moderate activity against the Gram-positive and Gram-negative bacteria.

  DOI：

  10.1007/s00044-011-9788-9

文献信息

• Gill, G. Bryon; Idris, Muhammad S. Hj.; Kirollos, Kirollos S., Journal of the Chemical Society. Perkin transactions I, 1992, # 18, p. 2355 - 2366
  作者：Gill, G. Bryon、Idris, Muhammad S. Hj.、Kirollos, Kirollos S.

  DOI：——

  日期：——
• Cobalt mediated ring contraction reaction of lapachol and initial antibacterial evaluation of naphthoquinones derived from lapachol
  作者：Kenneth O. Eyong、Senthil P. Kumar、Victor Kuete、Gabriel N. Folefoc、Henrietta Langmi、Marion J. J. Meyer、Namrita Lall、Sundarababu Baskaran

  DOI：10.1007/s00044-011-9788-9

  日期：2012.8

  The synthesis of 2-hydroxy-2-(3-methylbut-2-enyl)-2H-indene-1,3-dione 3, from lapachol which involves a ring contraction via the Hooker intermediate 1,2-dihydroxy-2-(3-methylbut-2-en-1-yl)-3-oxo-2,3-dihydro-1H-indene-1-carboxylic acid 2 is described. Different pyranonaphthoquinone derivatives, obtained in our previous synthetic work, were screened for antimycobacterial (Mycobacterium tuberculosis) activity and against resistant strains of Gram-positive (Bacillus cereus and Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. The results indicated significant activity of all the tested samples against M. tuberculosis and only moderate activity against the Gram-positive and Gram-negative bacteria.