6-chloro-2-oxo-2H-chromene-4-carbaldehyde

• 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: 6-chloro-2-oxo-2H-chromene-4-carbaldehyde
• 英文别名: 6-chloro-4-formylcoumarin；6-Chloro-4-formylcoumarin；6-chloro-2-oxochromene-4-carbaldehyde
• 化学式: C₁₀H₅ClO₃
• 分子量: 208.601
• InChiKey: SGXYBVHPJZXVDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-2-oxo-2H-chromene-4-carbaldehyde 在 三乙烯二胺 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成
  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
• 作为产物：
  描述：

  6-羟基-4-甲基香豆素 在 selenium(IV) oxide 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 6-chloro-2-oxo-2H-chromene-4-carbaldehyde
  参考文献：
  名称：

  Microwave-Assisted Synthesis of Novel 2H-Chromene Derivatives Bearing Phenylthiazolidinones and Their Biological Activity Assessment

  摘要：

  制备了 6-羟基-2-氧代-2H-苯并吡喃-4-甲醛 (2)、6-氯-2-氧代-2H-苯并吡喃-4-甲醛 (3) 和 6-肼基-4-甲基-2H-苯并吡喃-2-酮 (5)，作为单药效基团关键中间体。在微波辅助和传统化学合成工艺下，将化合物 2、3 和 5 加入一系列多组分反应 (MCR)，以良好的产率获得了一系列三和/或四药效基团共轭物 8a、b、11、13、16、17、19 和 20。新合成的化合物通过红外光谱、核磁共振、13C-核磁共振、质谱和元素分析进行了表征。最后，对合成的化合物进行了生物活性筛选，结果表明它们对不同种类的细菌和真菌具有显著的抗菌活性。

  DOI：

  10.3390/molecules191219648

文献信息

• One-pot, green synthetic route for construction of coumarin C-4 bridged 2,6-dicyanoanilines and their photophysical study
  作者：Rashmi C. Kulkarni、S. Samundeeswari、Bahubali M. Chougala、Megharaja Holiyachi、Manohar V. Kulkarni、Lokesh A. Shastri

  DOI：10.1080/00397911.2016.1245751

  日期：2016.12.16

  conditions, avoids the use of toxic solvents, and gives excellent yield with high purity. All the synthesized compounds have been characterized by spectral analysis. Optical and thermal screening studies of all newly synthesized compounds showed excellent photophysical and thermal stability properties. GRAPHICAL ABSTRACT

  摘要 通过一锅三组分方法开发了一种高选择性和更有效的绿色方案，用于在乙醇水溶液中合成香豆素 2,6-二氰基苯胺。从机理上看，两分子丙二腈与醛和酮缩合生成加合物，通过形成两个新的 CC 键进行分子内环化，得到标题化合物。本方法提供了简化的纯化和环境友好的条件，避免使用有毒溶剂，并提供高纯度的优良收率。所有合成的化合物均已通过光谱分析表征。所有新合成化合物的光学和热筛选研究都显示出优异的光物理和热稳定性。图形概要
• Design and synthesis of coumarin–imidazole hybrid and phenyl-imidazoloacrylates as potent antimicrobial and antiinflammatory agents
  作者：Megharaja Holiyachi、S. Samundeeswari、Bahubali M. Chougala、Nirmala S. Naik、Jyoti Madar、Lokesh A. Shastri、Shrinivas D. Joshi、Sheshagiri R. Dixit、Suneel Dodamani、Sunil Jalalpure、Vinay A. Sunagar

  DOI：10.1007/s00706-017-2079-5

  日期：2018.3

  Pseudomonas spp. bacterial strains and two strains of fungi studies having Scopulariopsis spp. and Aspergillus terreus organisms. Similarly, antiinflammatory activity of all the compounds was screened against MMP-2 and MMP-9. Both antimicrobial and antiinflammatory results are excellent, among all compounds, sodium acrylate compounds are quite promising against microbial strains and matrix metalloproteins

  摘要在C4位合成了改进的单锅多组分三和四取代香豆素-咪唑杂化物的合成，收率良好。该反应在各种催化剂下进行，获得的优化条件结果令人满意。其中，三取代的香豆素-咪唑杂化化合物被转化为丙烯酸苯基-咪唑。此外，筛选所有新合成的化合物对革兰氏阳性弯曲杆菌和革兰氏阴性假单胞菌的抗菌活性。细菌菌株和两种真菌菌株的研究有鞘藻属。和曲霉生物。类似地，针对MMP-2和MMP-9筛选了所有化合物的抗炎活性。在所有化合物中，抗菌和抗炎效果都非常好，丙烯酸钠化合物在抵抗微生物菌株和基质金属蛋白（MMP）方面很有前途。所有分离的化合物均通过IR，NMR和质谱分析进行了表征。 图形概要
• Synthesis, characterization and molecular docking studies of substituted 4-coumarinylpyrano[2,3-c]pyrazole derivatives as potent antibacterial and anti-inflammatory agents
  作者：Bahubali M. Chougala、S. Samundeeswari、Megharaja Holiyachi、Lokesh A. Shastri、Suneel Dodamani、Sunil Jalalpure、Sheshagiri R. Dixit、Shrinivas D. Joshi、Vinay A. Sunagar

  DOI：10.1016/j.ejmech.2016.09.021

  日期：2017.1

  techniques. Most of the compounds exhibited promising antibacterial activity, in particular Gram-positive bacteria. The anti-inflammatory assay was evaluated against protein denaturation as well as HRBC membrane stabilization methods and compounds exhibit excellent anti-inflammatory activity in both methods. Molecular docking study has been performed for all the synthesized compounds with S. aureus dihydropteroate

  已开发出一种绿色，环保，高效的方案，并通过多组分反应（MCR）合成了一系列基于香豆素的吡喃并[2,3- c ]吡唑衍生物（3）。通过化合物（3）在酸性条件下的反应，分离出意外的3-香豆基-3-吡唑基丙酸（4）。此外，化合物（4）的分子内环化导致C 4 C 4色子（9），然后使用多种技术筛选这些化合物的生物学活性。大多数化合物表现出有希望的抗菌活性，特别是革兰氏阳性细菌。评估了抗炎测定的抗蛋白质变性以及HRBC膜稳定化方法，化合物在这两种方法中均表现出出色的抗炎活性。已经用金黄色葡萄球菌二氢蝶呤合成酶（DHPS）对所有合成的化合物进行了分子对接研究，获得的结果是很有希望的。
• Green approach for the synthesis of 4-coumarin-4<i>H</i>-pyrans from 4-formylcoumarins and their antibacterial study
  作者：Alpana Saxena、Lokesh Shastri、Vinay Sunagar

  DOI：10.1080/00397911.2017.1336557

  日期：2017.9.2

  ABSTRACT A series of 4H-pyranocoumarin derivatives have been successfully synthesized under eco-friendly condition using triethylamine as a catalyst in short reaction time with excellent yield at room temperature. All the synthesized compounds were characterized by spectral analysis and screened for their antibacterial activity against Escherichia coli and Staphylococcus aureus, the results are quite

  摘要 以三乙胺为催化剂，在环境友好的条件下，成功合成了一系列 4H-吡喃香豆素衍生物，在室温下反应时间短，收率高。所有合成的化合物均通过光谱分析和筛选对大肠杆菌和金黄色葡萄球菌的抗菌活性，结果很有希望。图形概要
• Highly stereoselective direct aldol reaction of 4-formylcoumarins with acetone catalyzed by L-proline in water–acetone mixtures
  作者：Megharaja Holiyachi、Samundeeswari L. Shastri、Bahubali M. Chougala、Lokesh A. Shastri、Vinay A. Sunagar

  DOI：10.1080/00397911.2016.1205197

  日期：2016.8.17

  aldol reactions have been developed for substituted 4-formylcoumarins with acetone in water using L-proline and phthalimido-prolinamide catalysts without use of additives. Stereoselective products obtained were in excellent yields (up to 97%) with high purity (up to 99%) and enatioselectivities (up to 95%). The isolated compounds were confirmed by infrared, NMR, high-performance liquid chromatography

  摘要 使用 L-脯氨酸和邻苯二甲酰亚胺-脯氨酰胺催化剂，在不使用添加剂的情况下，已开发出有机催化的直接分子间羟醛反应，用于在水中用丙酮取代 4-甲酰基香豆素。获得的立体选择性产物具有优异的产率（高达 97%）、高纯度（高达 99%）和对映选择性（高达 95%）。分离出的化合物经红外、核磁共振、高效液相色谱和质谱证实，其中一些经单晶X射线晶体学证实。图形概要