4-methyl-7-nonafluorobutylsulfonyloxy coumarin | 93131-78-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 4-methyl-7-nonafluorobutylsulfonyloxy coumarin
• 英文别名: (4-methyl-2-oxochromen-7-yl) 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
• CAS: 93131-78-3
• 化学式: C₁₄H₇F₉O₅S
• 分子量: 458.258
• InChiKey: DFSOGUWHSRYWEN-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C(Solv: ethanol (64-17-5))
• 沸点：
  406.8±45.0 °C(Predicted)
• 密度：
  1.643±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4-methyl-7-nonafluorobutylsulfonyloxy coumarin 在 C₉₄H₁₃₄O₄P₂Pd₂ 、 cesium fluoride 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以89%的产率得到7-fluoro-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  An Improved Catalyst System for the Pd-Catalyzed Fluorination of (Hetero)Aryl Triflates

  摘要：

  The stable Pd(0) species [(1,5-cyclooctadiene)(L.Pd)(2)] (L = AdBrettPhos) has been prepared and successfully evaluated as a precatalyst for the fluorination of aryl triflates derived from biologically active and heteroaryl phenols, challenging substrates for our previously reported catalyst system. Additionally, this precatalyst activates at room temperature under neutral conditions, generates 1,5-cyclooctadiene as the only byproduct, and leads to overall cleaner reaction profiles.

  DOI：

  10.1021/ol402859k
• 作为产物：
  描述：

  间苯二酚 在 吡啶 、 1-n-butyl-3-methylimidazolium chloroaluminate 作用下， 生成 4-methyl-7-nonafluorobutylsulfonyloxy coumarin
  参考文献：
  名称：

  4-Methyl-7-Amino/Amido Coumarin Derivatives as Potential Antimicrobials and Antioxidants

  摘要：

  一批先前合成的4-甲基-7-氨基和酰胺香豆素4a–u已被筛选其抗菌和抗氧化性能。与各自的标准相比，一些化合物表现出有前景的抗菌和抗真菌活性（MIC范围为4-64 μg/mL）。化合物4u显示出与标准环丙沙星相当的抗菌活性，而化合物4u和4t在与标准氟康唑相比时显示出有前景的抗真菌活性。针对拓扑异构酶的计算对接研究揭示了4u具有氢键和显著的疏水相互作用，这可能是其相对于其他化合物具有更优越抗菌活性的原因。化合物4c和4m显示出与标准BHT相当的抗氧化活性，这可以归因于存在供电子取代基。

  DOI：

  10.1007/s10600-020-03106-y

文献信息

• Cross-Coupling of Amide and Amide Derivatives to Umbelliferone Nonaflates: Synthesis of Coumarin Derivatives and Fluorescent Materials
  作者：Shane M. Hickey、Samuel O. Nitschke、Martin J. Sweetman、Christopher J. Sumby、Douglas A. Brooks、Sally E. Plush、Trent D. Ashton

  DOI：10.1021/acs.joc.0c00813

  日期：2020.6.19

  properties of aqueous-soluble derivatives were determined, and they displayed auxochrome-based variations. Gram-scale synthesis provided an acrylamide analogue, which was used to fabricate a fluorescent poly(2-hydroxylethyl methacrylate) (pHEMA) hydrogel that was resistant to leaching in ultrapure H2O. We envisage that our reported protocol to access 7-amino-4-methylcoumarin derivatives will find use toward

  描述了4-甲基伞形酮衍生的壬二酸酯与酰胺，氨基甲酸酯和磺酰胺之间的布赫瓦尔德-哈特维格交叉偶联反应。以良好至优异的产率制备了多种N-取代的7-氨基香豆素类似物。测定了水溶性衍生物的光物理性质，并且它们显示出基于色素的变化。克级合成提供了一种丙烯酰胺类似物，该丙烯酰胺类似物用于制造可抵抗超纯H 2 O浸出的荧光聚（甲基丙烯酸2-羟乙酯）（pHEMA）水凝胶。我们设想，我们报告的访问7-氨基-该领域的研究人员将发现4-甲基香豆素衍生物可用于开发基于荧光香豆素的新型荧光探针。
• Simultaneous exploration of TBAF·3H 2 O as a base as well as a solvating agent for the palladium catalyzed Suzuki cross-coupling of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation
  作者：M. Nibin Joy、Yadav D. Bodke、K.K. Abdul Khader、Ayyiliyath M. Sajith、Talavara Venkatesh、A.K. Ajeesh Kumar

  DOI：10.1016/j.jfluchem.2016.01.002

  日期：2016.2

  A concise, efficient and facile protocol for the synthesis of a variety of 4-methyl-7-aryl/heteroaryl coumarins has been developed by utilizing the palladium catalyzed Suzuki cross-coupling reaction of 4-methyl-7-nonafluorobutylsulfonyloxy coumarin with a wide range of electronically diverse boronic acids under microwave irradiation. In the presence of a suitable catalyst, ligand and base, the coupling

  通过利用钯催化的4-甲基-7-九氟丁基磺酰氧基香豆素与宽范围的钯催化的Suzuki交叉偶联反应，已开发出一种简捷，高效且简便的合成多种4-甲基-7-芳基/杂芳基香豆素的方案。微波辐射下各种电子硼酸的合成 在合适的催化剂，配体和碱的存在下，偶联反应顺利进行，以令人满意的至优异的产率得到联芳基。TBAF·3H 2的双重作用发现O作为溶剂以及溶剂，以及使用dppp作为具有适中咬合角（91°）的配体有助于反应成功。该优化条件的突出特征包括：反应时间短，产率高至优异以及对多种官能团的优异耐受性。
• A rapid and modified approach for C-7 amination and amidation of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation
  作者：M. Nibin Joy、Yadav D. Bodke、K. K. Abdul Khader、M. Syed Ali Padusha、Ayyiliyath M. Sajith、A. Muralidharan

  DOI：10.1039/c4ra01720j

  日期：——

  A rapid approach for the synthesis of an array of 4-methyl-7-substituted coumarins has been developed.

  已开发出一种合成4-甲基-7-取代香豆素阵列的快速方法。
• Synthesis of Coumarins Coupled with Benzamides as Potent Antimicrobial Agents
  作者：Muthipeedika Nibin Joy、Vasiliy A. Bakulev、Yadav D. Bodke、Sandeep Telkar

  DOI：10.1007/s11094-020-02245-4

  日期：2020.9

  A series of new coumarin derivatives coupled with benzamides have been synthesized and screened for their antimicrobial properties. Some compounds displayed promising antibacterial activity (MIC ranging within 5 – 150 μg/mL) and moderate antifungal activity as compared to the respective standards. Compounds 6p, 6l and 6m displayed promising antibacterial activity comparable with the standard drug ciprofloxacin, and compound 6m exhibited better antifungal activity in comparison to other synthesized compounds. In silico docking studies of the active compounds were carried out against the gyrase enzyme, and it was concluded that compound 6p exhibited significant hydrogen bonding and hydrophobic interactions which could be the plausible reason for its superior activity as compared to the other synthesized compounds.

  我们合成了一系列与苯甲酰胺联用的新型香豆素衍生物，并对它们的抗菌特性进行了筛选。与相应的标准物质相比，一些化合物显示出良好的抗菌活性（MIC 范围在 5 - 150 μg/mL 之间）和适度的抗真菌活性。化合物 6p、6l 和 6m 显示出与标准药物环丙沙星相当的抗菌活性，与其他合成化合物相比，化合物 6m 显示出更好的抗真菌活性。针对回旋酶对活性化合物进行了硅对接研究，得出的结论是化合物 6p 表现出明显的氢键和疏水相互作用，这可能是其活性优于其他合成化合物的合理原因。
• 7-Azaspiroketal as a unique and effective auxochrome moiety: demonstration in a fluorescent coumarin dye and application in cell imaging
  作者：Harish K. Indurthi、Pooja Goswami、Samarpita Das、Pallavi Saha、Biplob Koch、Deepak K. Sharma

  DOI：10.1039/d3nj04934e

  日期：——

  groups with azacyclic groups has been described as a promising auxochrome to improve the low fluorescent quantum yields (ΦF) of conventional fluorophores. However, the insufficient brightness and poor solubility of fluorophores pose a significant bottleneck for bioimaging. A new type of fluorescent coumarin dye was designed and synthesized using 7-azaspiroketals as the electron-donating auxochrome group

  用氮杂环基团取代给电子的N , N-二烷基基团被描述为一种有前途的助色剂，可改善传统荧光团的低荧光量子产率 ( Φ F )。然而，荧光团的亮度不足和溶解度差给生物成像带来了重大瓶颈。以7-氮杂螺缩酮为供电子助色基团，设计并合成了一种新型荧光香豆素染料。这种修饰产生了具有改善的溶解度和亮度的高质量香豆素荧光团。据我们所知，这是在任何类别的供体-受体染料中使用顶点-N-取代的氮杂螺缩酮作为电子供体基团的第一份报告。此外，这些新型染料在活细胞生物成像中的成功应用已得到证实。