8H-Pyrano[2,3-f]chromen-2-one | 6054-08-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8H-Pyrano[2,3-f]chromen-2-one
• 英文别名: Pyrano[2,3-f]chromenone
• CAS: 6054-08-6
• 化学式: C₁₂H₈O₃
• 分子量: 200.194
• InChiKey: YEUDWDRBSRVYSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8H-Pyrano[2,3-f]chromen-2-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成
  参考文献：
  名称：

  Pyranocoumarins as potential photochemotherapeutic agents: theoretical and physico-chemical studies on the mechanism of action

  摘要：

  The interactions between 2 angular pyranocoumarins and DNA have been studied in both ground and excited states. The compounds are able to intercalate inside DNA in a non-covalent manner and, under UV-A irradiation, to photobind covalently, forming pyran-side monoadducts and cross-links. The crystal structure of 4,6-dimethylpyranocoumarin was determined by X-ray diffraction techniques, and molecular arrangements in both ground and excited (singlet and triplet) states were calculated by the MNDO method. Results are discussed in terms of intercalation in the ground state, as shown by linear dichroism measurements, and covalent photobinding to pyrimidine bases of DNA under UV-A excitation.

  DOI：

  10.1016/0223-5234(91)90130-f
• 作为产物：
  描述：

  7-(propynyloxy)-2H-chromen-2-one 以 various solvent(s) 为溶剂， 以41%的产率得到8H-Pyrano[2,3-f]chromen-2-one
  参考文献：
  名称：

  合成8-去甲基黄嘌呤和8-去甲基正己烷的甲基衍生物，潜在的抗增殖剂

  摘要：

  合成了许多与8-去甲基黄嘌呤和8-去甲基正己烷有关的吡喃香豆素的新甲基衍生物。通过在沸腾的N，N-二乙基苯胺的7-羟基香豆素的合适的甲基衍生物的炔丙基或甲基炔丙基醚中环化进行合成。甲基已被引入到看起来最有希望增强化合物对DNA的光反应性的位置。

  DOI：

  10.1002/jhet.5570240234

文献信息

• Synthesis of pyrano[2,3-<i>f</i>]chromen-2-ones <i>vs.</i> pyrano[3,2-<i>g</i>]chromen-2-ones through site controlled gold-catalyzed annulations
  作者：Antonio Arcadi、Alessia Ciogli、Giancarlo Fabrizi、Andrea Fochetti、Roberta Franzini、Francesca Ghirga、Antonella Goggiamani、Antonia Iazzetti

  DOI：10.1039/c9ob01695c

  日期：——

  Regioselective access to 10-substituted-2H,8H-pyrano[2,3-f]chromen-2-ones through the gold-catalyzed intramolecular hydroarylation of readily available 7-(prop-2-yn-1-yloxy)-2H-chromen-2-one derivatives at their C-8 congested position was investigated by tuning the electronic and steric properties of the ligand on the gold complex. On the other hand, the combination of the JohnPhosAu(MeCN)SbF6 catalyzed

  通过容易获得的7-（prop-2-yn-1-yloxy）-的金催化的分子内氢芳基化反应，对10-取代的2 H，8 H-吡喃并[2,3- f ] chromen -2- one进行区域选择性的访问。通过调节金络合物上配体的电子和位阻性质，研究了其C-8拥挤位置的2 H-铬-2--2-酮衍生物。另一方面，JohnPhosAu（MeCN）SbF 6的组合催化8-碘-7-（prop-2-yn-1-yloxy）-2H-铬-2--2-酮衍生物的分子内氢芳基化反应，然后进行选择性钯/甲酸C–I还原允许排他形成2 H，8 H-吡喃并[3,2- g] chromen-2-one区域异构体。这两个协议的开发提供了探索这些新的吡喃香豆素衍生物的生物学活性所需的通用合成工具。
• Efficient and Short Route for the Regioselective Synthesis of Highly Substituted, Angularly Fused Furano-, Pyrano-, and Pyrrolocoumarin/Quinolone Derivatives by Metal-Mediated Cyclization
  作者：K. C. Majumdar、Shovan Mondal、Buddhadeb Chattopadhyay

  DOI：10.1080/00397910903219559

  日期：2010.6.25

  A one-step efficacious method for the construction of a variety of substituted furano-, pyrano-, and pyrrolocoumarins and pyrroloquinolones in good to excellent yields has been developed.

  已经开发出一种一步有效的方法来构建各种取代的呋喃基、吡喃基和吡咯香豆素以及吡咯并喹诺酮类，其产率很高。
• Cesium Fluoride-mediated Claisen Rearrangements of Phenyl Propargyl Ethers: Substituent Effects of an ortho-Alkoxy Group on the Benzene Ring or Modified Propargyl Residues
  作者：Tsutomu Ishikawa、Akiko Mizutani、Chizue Miwa、Yumie Oku、Naoko Komano (nee Ohkubo)、Atsuya Takami、Toshiko Watanabe

  DOI：10.3987/com-97-7946

  日期：——

  The expected 7-alkoxy-2-methylbenzo [b]furans were effectively given in the CsF-mediated Claisen rearrangement of phenyl propargyl ethers with an o-alkoxy substituent on the benzene ring. On the other hand CsF did not affect the production of the corresponding benzo[b]furans when ethers, carrying a propargyl residue modified by either 1,1-dimethyl or 3-ethoxycarbonyl functions, were used as substrates in the rearrangement.
• Faulques; Rene; Royer, European Journal of Medicinal Chemistry, 1983, vol. 18, # 1, p. 9 - 14
  作者：Faulques、Rene、Royer、et al.

  DOI：——

  日期：——
• Corrigendum
  作者：Majumdar、Mondal, Shovan、Chattopadhyay, Buddhadeb

  DOI：10.1080/00397911.2010.534664

  日期：2010.11.3