4-甲酰基-5,6-苯并香豆素 | 106236-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 中文名称: 4-甲酰基-5,6-苯并香豆素
• 英文名称: 4-formyl-5,6-benzocoumarin
• 英文别名: 3-oxo-3H-benzo[f]chromene-1-carbaldehyde
• CAS: 106236-82-2
• 化学式: C₁₄H₈O₃
• 分子量: 224.216
• InChiKey: MCHKYQNWTDXUDR-UHFFFAOYSA-N

物化性质

• 沸点：
  470.8±40.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.28
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-甲酰基-5,6-苯并香豆素 在 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 6.0h， 生成 1-diazomethyl-3H-naphtho<2,1-b>pyran-3-one
  参考文献：
  名称：

  Studies on stable diazoalkanes as potential fluorogenic reagents. II. Ring-fused 4-diazomethylcoumarins.

  摘要：

  准备了几种环状融合的4-季铵基甲基香豆素4a-f，作为稳定的偶氮烃，并且探讨了它们在酸性物质荧光标记中的应用。最容易获得的产物4-季铵甲基-2H-萘[1,2-b]吡喃-2-酮4a，在硅胶催化剂的存在下能够与羧酸反应，并且在氟硼酸催化剂的存在下也能与醇反应，产生良产率的荧光酯和醚。

  DOI：

  10.1248/cpb.34.390
• 作为产物：
  描述：

  2-萘酚 在 硫酸 、 二甲基亚砜 作用下， 以 水 为溶剂， 生成 4-甲酰基-5,6-苯并香豆素
  参考文献：
  名称：

  Design, synthesis, characterization, and biological evaluation of pyrido[1,2-a]pyrimidinone coumarins as promising anti-inflammatory agents

  摘要：

  Pursuing our recent interest regarding antimicrobial and anti-inflammatory activities of coumarin derivatives, we have synthesized a series of coumarin-linked pyridopyrimidinones by using Baylis Hillman adduct in aqueous condition with high purity. Pyrido[1,2-a]pyrimidin-2-ones are important class of heterocyclic compounds because of their use in medicinal and agro chemistry as active agents. All these newly synthesized compounds were evaluated for their antimicrobial and anti-inflammatory activity. Coumarin pyridopyrimidinones showed excellent anti-inflammatory activity against both MMP-2 and MMP-9 gelatinase zymography, whereas considerable good activity against Gram-positive and Gram-negative bacterial strains; however, antifungal activity observed in these series is more or less inactive. The active compounds of these series would be promising structural templates for the development of novel and more efficient anti-inflammatory agent.

  DOI：

  10.1080/00397911.2017.1397698

文献信息

• Donor-acceptor pyran-2-ones: Absorption and fluorescence spectra of 4-substituted 2<i>H</i>-1-benzo/napthopyran-2-ones
  作者：Rajesh S. Kenny、Uday C. Mashelkar

  DOI：10.1002/jhet.5570430230

  日期：2006.3

  The absorption spectra and emission spectra of 4-substituted 2H-1-benzo/napthopyran-2-ones 3a-1 have been determined in THF and DMSO. The substituent at the 4-position of the 2H-benzo/napthopyran-2-one, establishes a compact conjugation pathway in which the pyran-2-one nucleus can act as an acceptor ring.

  已经确定了在THF和DMSO中4-取代的2 H -1-苯并/萘并吡喃-2-酮3a-1的吸收光谱和发射光谱。在2 H-苯并/萘并吡喃-2-酮的4位上的取代基建立了紧密的共轭途径，其中吡喃-2-一核可充当受体环。
• Effects of Base for the Efficient Synthesis of 4-Formylcoumarins and 4-Formylcarbostyrils
  作者：Megharaja Holiyachi、Samundeeswari L. Shastri、Bahubali M. Chougala、Lokesh A. Shastri

  DOI：10.1080/00397911.2014.981754

  日期：2015.4.18

  The first efficient transformation of 4-bromomethylcoumarins and 4-bromomethylcarbostyrils to 4-formylcoumarins and 4-formylcarbostyril under aqueous conditions has been achieved by modifying the Kornblum method, resulting in excellent yield. The experimental method is very simple and economical; no further purification is required and the experimental conditions have been optimized. All the isolated compounds were characterized by infrared, NMR, and mass spectroscopy, and some of the compounds have been analyzed by single-crystal x-ray analysis.
• Gudimani, Parashuram; Holiyachi, Megharaja; Joshi, Shrinivas D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2021, vol. 60, # 3, p. 418 - 432
  作者：Gudimani, Parashuram、Holiyachi, Megharaja、Joshi, Shrinivas D.、Madar, Jyoti M.、Naik, Nirmala S.、Pawar, Varsha、Shastri, Lokesh A.、Shastri, Samundeeswari L.、Shettar, Arun K.、Sungar, Vinay A.

  DOI：——

  日期：——
• Synthesis, in vitro biological evaluation and molecular docking study of coumarin-1,4-dihydropyridine derivatives as potent anti-inflammatory agents
  作者：Madar, Jyoti M.、Shastri, Lokesh A.、Shastri, Samundeeswari L.、Holiyachi, Megharaja、Naik, Nirmala S.、Gudimani, Parashuram、Pawar, Varsha、Shettar, Arun K.、Joshi, Shrinivas D.、Sungar, Vinay A.

  DOI：10.56042/ijc.v61i2.60711

  日期：——