7-ethynyl-4-hydroxymethyl-chromen-2-one | 736957-97-4

• 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: 7-ethynyl-4-hydroxymethyl-chromen-2-one
• 英文别名: 7-Ethynyl-4-(hydroxymethyl)chromen-2-one
• CAS: 736957-97-4
• 化学式: C₁₂H₈O₃
• 分子量: 200.194
• InChiKey: YCIKUBKEJOERKK-UHFFFAOYSA-N

物化性质

• 沸点：
  408.6±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-ethynyl-4-hydroxymethyl-chromen-2-one 在 tris-triazole ligand 、 potassium acetate 、 copper(II) sulfate 、 维生素 C 作用下， 以 乙腈 为溶剂， 反应 50.0h， 生成 succinic acid mono{7-[1-(4-carboxybenzyl)-1H-[1,2,3]triazol-4-yl]-2-oxo-2H-chromen-4-ylmethyl} ester
  参考文献：
  名称：

  A Fluorogenic Probe for the Copper(I)-Catalyzed Azide−Alkyne Ligation Reaction:  Modulation of the Fluorescence Emission via ³(n,π*)−(π,π*) Inversion

  摘要：

  Chemoselective ligation reactions represent a powerful approach for labeling of proteins or small molecules in a biological environment. We report here a fluorogenic probe that is activated by click chemistry, a highly versatile bio-orthogonal and chemoselective ligation reaction which is based on the azide moiety as the functional group. The electron-donating properties of the triazole ring that is formed in the course of the coupling reaction was effectively utilized to modulate the fluorescence output of an electronically coupled coumarin fluorophore. Under physiological conditions the probe is essentially nonfluorescent and undergoes a bright emission enhancement upon ligation with an azide. Time-resolved emission spectroscopy and semiempirical quantum-mechanical calculations suggest that the fluorescence switching is due to an inversion of the energy ordering of the emissive 1(pi,pi*) and nonemissive 3(n,pi*) excited states. The rapid kinetics of the ligation reaction render the probe attractive for a wide range of applications in biology, analytical chemistry, or material science.

  DOI：

  10.1021/ja049684r
• 作为产物：
  描述：

  4-(hydroxymethyl)-2-oxo-2H-chromen-7-yl trifluoromethanesulfonate 在 甲醇 、 四(三苯基膦)钯 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 36.25h， 生成 7-ethynyl-4-hydroxymethyl-chromen-2-one
  参考文献：
  名称：

  A Fluorogenic Probe for the Copper(I)-Catalyzed Azide−Alkyne Ligation Reaction:  Modulation of the Fluorescence Emission via ³(n,π*)−(π,π*) Inversion

  摘要：

  Chemoselective ligation reactions represent a powerful approach for labeling of proteins or small molecules in a biological environment. We report here a fluorogenic probe that is activated by click chemistry, a highly versatile bio-orthogonal and chemoselective ligation reaction which is based on the azide moiety as the functional group. The electron-donating properties of the triazole ring that is formed in the course of the coupling reaction was effectively utilized to modulate the fluorescence output of an electronically coupled coumarin fluorophore. Under physiological conditions the probe is essentially nonfluorescent and undergoes a bright emission enhancement upon ligation with an azide. Time-resolved emission spectroscopy and semiempirical quantum-mechanical calculations suggest that the fluorescence switching is due to an inversion of the energy ordering of the emissive 1(pi,pi*) and nonemissive 3(n,pi*) excited states. The rapid kinetics of the ligation reaction render the probe attractive for a wide range of applications in biology, analytical chemistry, or material science.

  DOI：

  10.1021/ja049684r

文献信息

• μ-Hydroxyl trinuclear copper(ii) clusters: reactivity and unusual formation in the three-component synthesis of 1,2,3-triazoles in aqueous media
  作者：Yuan-Bo Cai、Lei Liang、Jing Zhang、Hao-Ling Sun、Jun-Long Zhang

  DOI：10.1039/c3dt32906b

  日期：——

  copper(II) complexes (Cu-1 and Cu-5), we found that the μ-OH trinuclear copper(II) complex (Cu-6) was the active catalyst precursor. Through analysing the reaction intermediates we found that Cu(II) was partially reduced to Cu(I) and an adduct formed during catalytic process, which involves the alkyne coordinating to the Cu centers. This is the first example where a μ-OH trinuclear copper(II) complex has

  μ-羟基三核铜（II）化合物，其核心结构非常类似于多铜氧化酶的中心部分，已经得到了广泛的研究，并且已经证实了原型在C–H键氧化中的重要性。在研究过程中，Cu（II）Salens催化三组分（叠氮化钠，环氧化物和非活化末端炔烃1,3-Huisgen环加成反应，我们观察到由三个（R，R）-N-（5-磺基水杨基亚基）-1,2支撑的μ-OH桥接三核铜簇的异常形成-二氨基环己烷配体（Cu-6）在催化过程中。更有趣的是，通过对单核铜（II）配合物（Cu-1和Cu-5）的活性进行比较研究，我们发现μ-OH三核铜（II）配合物（Cu-6）是活性催化剂前体。通过分析反应中间体，我们发现Cu（II）被部分还原为Cu（II）I）和在催化过程中形成的加合物，其涉及与Cu中心配位的炔。这是第一个在催化氧化以外的铜催化反应中分离出μ-OH三核铜（II）配合物的第一个例子，这为研究μ-OH铜簇可能是铜催化反应中的中间体提供了有价值的线索。水性介质。
• Synthesis, photophysical properties and in vitro evaluation of a chlorambucil conjugated ruthenium(<scp>ii</scp>) complex for combined chemo-photodynamic therapy against HeLa cells
  作者：Jing-Xiang Zhang、Mei Pan、Cheng-Yong Su

  DOI：10.1039/c7tb00702g

  日期：——

  agent, but problems like drug instability, "off-target" binding and in situ monitoring after administration often limit its clinical application. In this regard, we designed a new heteroleptic Ru(ii) complex CHL-RuL, bearing a CHL conjugated pendant, which is desired to serve as an image-guided chemo-photodynamic combined theranostic agent. CHL-RuL shows considerable promise as a photosensitizer for

  与常规化学疗法相比，化学疗法与光动力疗法的组合可以提高治疗效率并减少副作用。苯丁酸氮芥（CHL）是一种DNA烷基化剂，但是诸如药物不稳定，“脱靶”结合和给药后就地监测等问题通常会限制其临床应用。在这方面，我们设计了一种带有CHL共轭侧基的新型杂配Ru（ii）复合物CHL-RuL，希望将其用作图像引导的化学光动力组合治疗剂。CHL-RuL作为双光子激发光动力疗法的光敏剂显示出广阔的前景：强且宽的UV-Vis吸收带集中在400 nm左右，强红色发射（〜702 nm），在微秒级具有长寿命，中等单线态氧量子产率 和显着的两光子吸收截面（118 GM）。更有趣的是，这种化学修饰使CHL-RuL在HeLa细胞中具有更大的细胞摄取和明显的线粒体积累。此外，相对于正常的MRC-5细胞，CHL-RuL对癌细胞HeLa细胞显示出轻微的选择性细胞毒性。MTT分析结果和双光子扫描细胞成像表明，CHL-RuL对He
• One-Step Derivatization of Reducing Oligosaccharides for Rapid and Live-Cell-Compatible Chelation-Assisted CuAAC Conjugation
  作者：Takuya Machida、Nicolas Winssinger

  DOI：10.1002/cbic.201600003

  日期：2016.5.3

  Chelation‐assisted click chemistry at micromolar copper concentrations: A simple procedure enabling functionalization of unprotected reducing oligosaccharides and rapid glycoconjugation at low copper concentrations is reported. It can be used to functionalize biomolecules bearing alkyne moieties introduced through metabolic labeling, including in live cells.

  在微摩尔铜浓度下的螯合辅助点击化学：据报道，一种简单的方法可以使未保护的还原性寡糖功能化，并在低铜浓度下实现快速的糖缀合。它可用于功能化带有通过代谢标记引入的炔烃部分的生物分子，包括在活细胞中。
• Template-Directed Fluorogenic Oligonucleotide Ligation Using “Click” Chemistry: Detection of Single Nucleotide Polymorphism in the Human p53 Tumor Suppressor Gene
  作者：Huabing Sun、Xiaohua Peng

  DOI：10.1021/bc4001678

  日期：2013.7.17

  into oligonucleotides, which were then used in highly efficient DNA interstrand cross-linking and ligation reactions via “click” chemistry. The template-directed fluorogenic ligation “click” chemistry reaction was used for single nucleotide polymorphism analysis, where the target DNA catalyzes the ligation of two nonfluorescent probes to generate a fluorescent product. The upstream oligonucleotide probe

  合成了一种新型的非荧光炔烃修饰的香豆素亚磷酰胺并将其成功掺入寡核苷酸中，然后通过“点击”化学将其用于高效的DNA链交联和连接反应中。模板指导的荧光连接“点击”化学反应用于单核苷酸多态性分析，其中目标DNA催化两个非荧光探针的连接以产生荧光产物。上游寡核苷酸探针是非荧光炔修饰的香豆素，下游探针是叠氮化物修饰的寡核苷酸。当与完全互补的模板结合时，寡核苷酸被连接以产生在连接点带有荧光团的荧光产物。