2H-4,8-dimethylfuro[2',3':5,6]naphtho[1,2-b]pyran-2-one | 75550-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2H-4,8-dimethylfuro[2',3':5,6]naphtho[1,2-b]pyran-2-one
• 英文别名: 2,6-dimethyl-[1]benzofuro[7,6-h]chromen-8-one
• CAS: 75550-49-1
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: NHBONQRTTUFXGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2H-4,8-dimethylfuro[2',3':5,6]naphtho[1,2-b]pyran-2-one 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(phthalimidylmethyl)-2,6-dimethylfuro[2',3':5,6]naphtho[1,2-b]pyran-8-one
  参考文献：
  名称：

  Synthesis of Novel DNA-Intercalating Naphthopyrone Derivatives with Improved Water Solubility and Photophysical Properties

  摘要：

  DOI：

  10.1007/pl00010289
• 作为产物：
  描述：

  4-甲基-7-羟基-8-硝基香豆素 在 potassium carbonate 、 N,N-二乙基苯胺 作用下， 以 丙酮 为溶剂， 反应 39.0h， 生成 2H-4,8-dimethylfuro[2',3':5,6]naphtho[1,2-b]pyran-2-one
  参考文献：
  名称：

  Synthesis, crystal structure, and properties of 2H-4,8-dimethylfuro[2′,3′:5,6]naphtho[1,2-b]pyran-2-one, a novel DNA intercalator

  摘要：

  The furonaphthopyrone 6, a novel DNA intercalator, was synthesized in two steps (ca. 56% overall yield) starting from naphthopyrone 3. The new naphthopyrone derivatives 4 and 6 were fully characterized and the absorption and fluorescence spectroscopic properties of 6 were determined. The dark interactions of furonaphthopyrone 1 and 6 with DNA have been investigated by a fluorescence quenching technique and their apparent Scatchard binding constants were calculated. The crystal structure of 6 was determined. The planarity of 6 and the geometry of the active double bond between the alpha-pyrone and the furan moieties of 6 suggest that furonaphthopyrones are efficient monofunctional DNA intercalators.

  DOI：

  10.1007/bf00807082

文献信息

• Qian, Xuhong; Huang, Tian-Bao; Wei, Dong-Zhi, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 4, p. 715 - 718
  作者：Qian, Xuhong、Huang, Tian-Bao、Wei, Dong-Zhi、Zhu, Dong-Hui、Fan, Ming-Cai、Yao, Wei

  DOI：——

  日期：——
• Synthesis of Novel DNA-Intercalating Naphthopyrone Derivatives with Improved Water Solubility and Photophysical Properties
  作者：Zhi-Fu Tao、Mingcai Fan、Xuhong Qian

  DOI：10.1007/pl00010289

  日期：1999.9
• Synthesis, crystal structure, and properties of 2H-4,8-dimethylfuro[2′,3′:5,6]naphtho[1,2-b]pyran-2-one, a novel DNA intercalator
  作者：Xuhong Qian、Zhi-Fu Tao、Dongzhi Wei、Jie Sun

  DOI：10.1007/bf00807082

  日期：1996.5

  The furonaphthopyrone 6, a novel DNA intercalator, was synthesized in two steps (ca. 56% overall yield) starting from naphthopyrone 3. The new naphthopyrone derivatives 4 and 6 were fully characterized and the absorption and fluorescence spectroscopic properties of 6 were determined. The dark interactions of furonaphthopyrone 1 and 6 with DNA have been investigated by a fluorescence quenching technique and their apparent Scatchard binding constants were calculated. The crystal structure of 6 was determined. The planarity of 6 and the geometry of the active double bond between the alpha-pyrone and the furan moieties of 6 suggest that furonaphthopyrones are efficient monofunctional DNA intercalators.