3,3'-(4-pyridylmethylene)-bis(4-hydroxy-2H-chromen-2-one) | 392290-55-0

• 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: 3,3'-(4-pyridylmethylene)-bis(4-hydroxy-2H-chromen-2-one)
• 英文别名: 3,3'-(pyridine-4-ylmethylene)bis(4-hydroxy-2H-chromen-2-one)；3,3'-[(Pyridin-4-yl)methylene]bis(4-hydroxy-2H-1-benzopyran-2-one)；4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)-pyridin-4-ylmethyl]chromen-2-one
• CAS: 392290-55-0
• 化学式: C₂₄H₁₅NO₆
• mdl: MFCD00839110
• 分子量: 413.386
• InChiKey: AJQRDMVKOFZTNT-UHFFFAOYSA-N

物化性质

• 熔点：
  261-263 °C(Solv: 1,4-dioxane (123-91-1))
• 沸点：
  721.7±60.0 °C(Predicted)
• 密度：
  1.560±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  sodium hydroxide 、 neodymium(III) nitrate hexahydrate 、 3,3'-(4-pyridylmethylene)-bis(4-hydroxy-2H-chromen-2-one) 以 水 为溶剂， 生成 Nd(p-PyDC(2-))(OH)*2H2O
  参考文献：
  名称：

  Theoretical and spectroscopic studies of pyridyl substituted bis-coumarins and their new neodymium (III) complexes

  摘要：

  Ab initio, DFT and spectroscopic studies of 3,3 '-(o-pyridinomethylene)di-[4-hydroxycoumarin], 3,3 '-(m-pyridinomethylene)di-[4-hydroxycoumarin] and 3,3 '-(p-pyridinomethylene)di-[4-hydroxycoumarin] were performed. The molecular and electronic structures of the compounds were investigated using accurate HF and B3LYP/6-31G(d) calculations. Molecular quantities as vertical ionization potential, electron affinity, electronegativity, hardness and electrophilicity indices of the neutral species were calculated and discussed. Molecular electrostatic potential was considered as an additional molecular characteristic for predicting the most probable sites for electrophilic attack. The molecular structure and quantities of the dianionic species, which are active in solution, were calculated and discussed. The theoretical results suggested that both carbonyl and both hydroxyl oxygen atoms are preferred binding sites for electrophilic attack, in particular for a metal coordination. Further, the coordination abilities of the compounds were studied in complexation reactions with Nd(III). Complexes of Nd(III) with o-, m- and p-3,3 '-(pyridinomethylene)di-[4-hydroxycoumarin] were synthesized and characterized by different physicochemical methods: elemental analysis, IR, H-1 NMR spectroscopies and mass spectral data. The experimental data confirmed the theoretical predictions that the ligands in Nd(III) complexes are tetradentate and bound the metal ion through both carbonyl and both deprotonated hydroxyl oxygen atoms. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.chemphys.2005.01.026
• 作为产物：
  描述：

  4-吡啶甲醛 、 4-羟基香豆素 在 1,3-bis(carboxymethyl)-1H-benzo[d]imidazol-3-ium bromide coated on copper oxide nanoparticles 作用下， 以 neat (no solvent) 为溶剂， 反应 3.0h， 以93%的产率得到3,3'-(4-pyridylmethylene)-bis(4-hydroxy-2H-chromen-2-one)
  参考文献：
  名称：

  两性离子液体（ZIL）包覆的CuO可作为通过机械化学法通过一锅多组分反应绿色合成双香豆素衍生物的有效催化剂†

  摘要：

  使用两性离子液体（ZIL）涂覆的氧化铜（CuO）和机械球磨，已经开发了一种方便，无溶剂的双香豆素合成策略。的ZIL从咪唑/苯并咪唑和磺酸/羧酸盐基于部分制造。ZIL的使用提供了一个有趣的多功能机会，可以使用阴离子部分将它们固定在CuO上，而阳离子部分则可以自由用于催化应用。使用扫描电子显微镜，透射电子显微镜，能量色散X射线光谱，粉末X射线衍射，循环伏安法，固态紫外可见吸收和光谱发射法对杂化催化剂进行了充分表征。他们三个发现生成的基于ZIL的和CuO偶联的杂化催化剂（ZIL @ CuO1-3）具有各种尺寸，形状，光物理特征和电化学性质。ZIL和CuO在ZIL @ CuO1中的超分子组装与其各自的母体组分以及其他两种杂化材料ZIL @ CuO2-3相比，催化活性大大提高。。通过改变所用球的数量，研磨时间和研磨速度来优化反应条件。使用质子-核磁光谱法阐明了反应机理，并使用光谱法充分鉴定了所有最终

  DOI：

  10.1039/c6nj03763a

文献信息

• The magnetic nanostructured natural hydroxyapatite (HAP/Fe3O4 NPs): an efficient, green and recyclable nanocatalyst for the synthesis of biscoumarin derivatives under solvent-free conditions
  作者：Batool Akhlaghinia、Parvin Sanati、Arezou Mohammadinezhad、Zeinab Zarei

  DOI：10.1007/s11164-019-03788-2

  日期：2019.5

  The magnetic nanostructured natural hydroxyapatite (HAP/Fe3O4 NPs) as a novel magnetic nanocatalyst was synthesized and fully characterized. The excellent catalytic activity of HAP/Fe3O4 NPs was investigated in the synthesis of biscoumarin derivatives under mild, green and solvent-free conditions. A series of aromatic (bearing different functional groups), heteroaromatic and aliphatic aldehydes have

  摘要合成并充分表征了 磁性纳米结构天然羟基磷灰石（HAP / Fe 3 O 4 NPs）。HAP / Fe 3 O 4的优异催化活性在温和，绿色和无溶剂条件下合成双香豆素衍生物中研究了NP。一系列芳香族（具有不同的官能团），杂芳香族和脂肪族醛已被转化为双香豆素，具有良好的分离产率。本方法与绿色化学原理非常吻合的显着优点是：催化剂便宜，无毒，易于处理且可重复使用多达六次循环，纳米结构催化剂的磁分离，后处理简单，反应时间短，产品的高收率和使用无溶剂条件。 图形概要
• Trityl bromide versus nano-magnetic catalyst in the synthesis of henna-based xanthenes and bis-coumarins
  作者：Mahmoud Zarei、Mohammad Ali Zolfigol、Ahmad Reza Moosavi-Zare、Ehsan Noroozizadeh

  DOI：10.1007/s13738-017-1155-4

  日期：2017.10

  trityl bromide (TrBr) as a new, efficient, mild and neutral catalyst was used for the synthesis of henna-based xanthenes (aryl-5H-dibenzo[b,i]xanthene-5,7,12,14(13H)-tetraones) and bis-coumarins by in situ generation of trityl carbocation under solvent-free conditions in comparison with [Fe3O4@SiO2@(CH2)3-Im-SO3H]Cl as an acidic and reusable catalyst for the first time. Graphical Abstract

  摘要在这项工作中，三苯甲基溴（TrBr）作为一种新型，高效，温和和中性的催化剂被用于合成指甲花基黄嘌呤（芳基5 H-二苯并[ b，i ]吨蒽5,7,12,14与（Fe 3 O 4 @SiO 2 @（CH 2）3 -Im-SO 3 H] Cl为酸性相比，在无溶剂条件下通过原位生成三苯甲基碳正离子合成（13H）-四酮）和双香豆素首次可重复使用的催化剂。 图形概要
• BiVO4-NPs: an efficient nano-catalyst for the synthesis of biscoumarins, bis(indolyl)methanes and 3,4-dihydropyrimidin-2(1H)-ones (thiones) derivatives
  作者：Farhad Shirini、Monireh Pourghasemi Lati

  DOI：10.1007/s13738-016-0959-y

  日期：2017.1

  4-dihydropyrimidin-2(1H)-ones (thiones) derivatives. The structures of the products were characterized by IR, 1H NMR and 13C NMR spectroscopy and comparison with the authentic samples. Easy work-up procedure, excellent yields, short reaction times and reusability of the catalyst are some advantages of this work. In addition, in this article and for the first time, the preparation of 3,4-dihydropyrimidin-2(1H)-ones

  BiVO 4 -NPs可用作促进双香豆素，双（吲哚基）甲烷和3,4-二氢嘧啶-2（1 H）-ones（thiones）衍生物合成的有效且可重复使用的纳米催化剂。产物的结构通过IR，1 H NMR和13 C NMR光谱表征，并与真实样品进行比较。简便的后处理程序，优异的收率，较短的反应时间和催化剂的可重复使用性是这项工作的一些优势。另外，在本文中并且首次报道了从醛的被保护的衍生物包括肟，半咔唑酮和1,1-二乙酸酯制备3,4-二氢嘧啶-2（1 H）-酮和-硫酮的报道。
• Heterogeneous <scp> SO ₃ H </scp> @ <scp> Fe ₃ O ₄ </scp> magnetic nanocatalyst as an efficient and reusable medium for the synthesis of 3,3′‐(arylmethylene)‐bis‐(4‐hydroxycoumarin), bis‐(indolyl)‐methane, and 1,8‐dioxo‐octahydroxanthene derivatives
  作者：Xiaobo Wu、Wan‐Xi Peng

  DOI：10.1002/jccs.202000087

  日期：2020.11

  This work aimed to synthesize a new heterogeneous catalyst (SO3H@Fe3O4 magnetic nanoparticles) and the study of its catalytic behavior in synthesizing 3,3′‐(arylmethylene)‐bis‐(4‐hydroxycoumarin), bis‐(indolyl)‐methane, and 1,8‐dioxo‐octahydroxanthene derivatives. The characterization of obtained material has been performed by means of Fourier‐transform infrared spectroscopy, thermogravimetric analysis

  这项工作旨在合成一种新的非均相催化剂（SO 3 H @ Fe 3 O 4磁性纳米粒子），并研究其在合成3,3'-（芳基亚甲基）-双-（4-羟基香豆素），双-（吲哚基）-甲烷和1,8-二氧代-八氢氧杂蒽衍生物。通过傅立叶变换红外光谱，热重分析，X射线衍射，振动样品磁力计和透射电子显微镜对获得的材料进行表征。与以前的方法相比，这种新方法的主要特性是反应时间短，反应条件温和，通过永久磁场简单回收催化剂，具有出色的收率，并且催化剂可重复使用至少六次。
• Sulfonated rice husk ash (RHA-SO3H) as a highly efficient and reusable catalyst for the synthesis of some bis-heterocyclic compounds
  作者：Mohadeseh Seddighi、Farhad Shirini、Manouchehr Mamaghani

  DOI：10.1039/c3ra44053b

  日期：——

  Sulfonated rice husk ash (RHA-SO3H), a newly reported solid acid catalyst, was efficiently used for the synthesis of 4,4′-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols), 3,3′-(arylmethylene)-bis-(4-hydroxycoumarins) and bis(indolyl)methanes. The procedure gave the products in excellent yields within very short reaction times under mild and green conditions. Also this catalyst can be reused several times without appreciable loss of its catalytic activity.

  磺化稻壳灰（RHA-SO3H），一种新近报道的固体酸催化剂，被高效地用于合成4,4′-（芳基亚甲基）-双-（3-甲基-1-苯基-1H-吡唑-5-醇）、3,3′-（芳基亚甲基）-双-（4-羟基香豆素）以及双（吲哚基）甲烷。该方法在温和且环保的条件下，利用极短的反应时间即可获得优异的产率。此外，该催化剂可多次重复使用，且其催化活性无明显损失。