13-phenyl-12H-pyrano[2,3-b:6,5-b’]dichromene-12,14(13h)-dione | 64191-25-9

• 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: 13-phenyl-12H-pyrano[2,3-b:6,5-b’]dichromene-12,14(13h)-dione
• 英文别名: 7-phenyl-7H-bis-[1]benzopyrano[4,3-b:3',4'-c]pyran-6,8-dione；9-phenyl-1,8-dioxo-9H-dibenzo[c,h]-2,7,10-trioxanthene；7-phenyl-4aH-pyrano[3,2-c:5,6-c']dichromene-6,8-dione；7-phenyl-7H-pyrano[3,2-c:5,6-c']dichromene-6,8-dione；3,3'-benzylidene-4,4'-epoxydicoumarin；7-phenyl-7H-pyrano[3,2-c;5,6-c'] dichromium ene-6,8-dione；7-phenyl-6H,7H,8H-pyrano[3,2-c:5,6-c']dichromene-6,8-dione；13-phenyl-2,10,16-trioxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4,6,8,17,19,21-octaene-11,15-dione
• CAS: 64191-25-9
• 化学式: C₂₅H₁₄O₅
• mdl: MFCD02163992
• 分子量: 394.383
• InChiKey: PEWKLAOLUAHLOK-UHFFFAOYSA-N

物化性质

• 熔点：
  393-395 °C
• 沸点：
  668.5±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,3'-phenylmethylene-bis-4-hydroxycoumarin 在 乙酸酐 、 二甲基亚砜 作用下， 反应 0.03h， 以66%的产率得到13-phenyl-12H-pyrano[2,3-b:6,5-b’]dichromene-12,14(13h)-dione
  参考文献：
  名称：

  Reaction of Dimethyl Sulfoxide-Acetic Anhydride with 4-Hydroxy-coumarin and Its Derivatives Under Microwave Conditions

  摘要：

  在微波条件下合成的4-羟基香豆素和各种双香豆素在相同条件下用DMSO-Ac2O试剂处理，得到了不同的产物。文献中报告的常规反应方法与此进行了比较，并首次在最短时间内通过微波条件获得了更高的产量。

  DOI：

  10.14233/ajchem.2013.13483

文献信息

• A new approach for the synthesis of biologically active chromene compounds using a photo catalyst TiO₂-Ag
  作者：George Kupar Kharmawlong、Ridaphun Nongrum、John Elisa Kumar、Bhusan Chhetri、Arun Kumar Yadav、Rishanlang Nongkhlaw

  DOI：10.1080/00397911.2021.2016836

  日期：2022.1.17

  (EDS), and powder XRD technique and thermogravimetric analysis (TGA). In addition, the in-vitro study of helminths against S. obvelata were investigated and it was found that chromene derivatives were active against S. obvelata and showed no sign of acute toxicity in mice.

  摘要 报道了一种在室温可见光照射下以TiO 2掺杂Ag为光催化剂合成色烯衍生物的绿色高效方法。我们的方法的优点是反应条件干净，后处理程序简单，使用环保溶剂，催化剂可回收，最重要的是产品收率较高。发现该光催化剂可在短时间内高效合成色烯衍生物。采用傅里叶变换红外光谱(FT-IR)、透射电子显微镜(TEM)、扫描电子显微镜(SEM)、能量色散X射线光谱(EDS)、粉末XRD技术和热重分析(TGA)制备光催化剂并对其进行表征。 ）。此外，体外对蠕虫对S. obvelata的研究进行了调查，发现色烯衍生物对S. obvelata有活性，并且在小鼠中没有显示出急性毒性的迹象。
• Evaluation of Antibacterial Activities of 4-Hydroxycoumarin Derivatives
  作者：Yue Hu、Jing Li、Chang-Wei Lv、Di Qu、Zheng Hou、Min Jia、Jiang-Tao Li、Zi-Dan Zhang、Xiao-Xing Luo、Zhi Yuan、Ming-Kai Li

  DOI：10.1515/zpch-2015-0630

  日期：2016.1.28

  Three kinds of 4-hydroxycoumarin derivatives, namely, biscoumarins (1–4), epoxydicoumarins (5–8) and dihydropyrans (9–12), were synthesized and the antibacterial activity of each of them was evaluated. The result of preliminary bioassay shows that the lowest minimal inhibitory concentration (MIC) of compounds 1 and 2 against drug-sensitive S. aureus (ATCC 29213) and methicillin-resistant S. aureus (MRSA XJ 75302, Mu50, ATCC 700699 and USA 300) is 4–64 ug/mL. Additionally, there are two classical intramolecular O—H⋯O hydrogen bonds (HBs) in the structures of biscoumarins (1–4), and their corresponding HB energies were further calculated by the density functional theory (DFT) [B3LYP/6-31G*] method.

  摘要：合成了三种4-羟基香豆素衍生物，分别为双香豆素（1-4）、环氧双香豆素（5-8）和二氢吡喃（9-12），并评估了它们的抗菌活性。初步生物测定结果显示，化合物1和2对药物敏感型金黄色葡萄球菌（ATCC 29213）和耐甲氧西林金黄色葡萄球菌（MRSA XJ 75302、Mu50、ATCC 700699和USA 300）的最低最小抑制浓度（MIC）为4-64 ug/mL。此外，双香豆素（1-4）的结构中存在两个经典的分子内O—H⋯O氢键（HBs），并且它们的对应HB能量进一步通过密度泛函理论（DFT）[B3LYP/6-31G*]方法计算。
• Pseudo Multicomponent Reaction: Synthesis of Fused Pyrano Biscoumarin Analogs from 1,2-diols
  作者：Narasashetty Jagadishbabu、Kalegowda Shivashankar

  DOI：10.1002/jhet.2742

  日期：2017.3

  A simple and efficient method has been developed for the synthesis of fused pyrano biscoumarins using lead tetraacetate as an oxidizing agent by the condensation of one equivalent of 1,2‐diols and four equivalent of 4‐hydroxy coumarin in acetonitrile as solvent at 80°C with good to excellent yields.

  已开发出一种简单有效的方法，以四乙酸铅为氧化剂，通过在80°C于乙腈中缩合一当量的1,2-二醇和四当量的4-羟基香豆素作为氧化剂，合成熔融的吡喃双香豆素。产量高到极好。
• P₂O₅/SiO₂as a New, Efficient and Reusable Catalyst for Preparation of 4,4′-Epoxydicoumarins Under Solvent-free Conditions
  作者：Liqiang Wu、Xiao Wang

  DOI：10.1155/2011/849795

  日期：——

  An efficient solvent-free procedure for the preparation of 4,4′-epoxydicoumarins via the ondensation of 4-hydroxycoumarin with aldehydes in the presence of catalytic amount of phosphorus pentoxide/silica gel at 110^°C is described. The advantages of this method are generality, high yields, short reaction times, ease of product isolation, low cost and ecologically friendly.

  通过在110°C下在磷酸五氧化硅胶的催化作用下，将4-羟基香豆素与醛缩合，制备4,4′-环氧基香豆素的高效无溶剂方法被描述。该方法的优点包括通用性高、产率高、反应时间短、产品分离容易、成本低且环保友好。
• DABCO-modified super-paramagnetic nanoparticles as an efficient and water-compatible catalyst for the synthesis of pyrano[3,2-<i>c</i>:5,6-<i>c</i>']dichromene-6,8-dione derivatives under mild reaction conditions
  作者：Zahra Heydari、Saeed Bahadorikhalili、Parviz Rashidi Ranjbar、Mohammad Mahdavi

  DOI：10.1002/aoc.4561

  日期：2018.12

  electron microscopy, vibrating‐sample magnetometer, thermogravimetric analysis, X‐ray photoelectron spectroscopy and Fourier‐transform infrared spectroscopy. This catalyst was used for the synthesis of pyrano[3,2‐c:5,6‐c']dichromene‐6,8‐dione derivatives. Several starting materials were used, and all of them led to the desired products in high isolated yields (19 examples). The catalyst also showed very

  本文基于超顺磁性氧化铁纳米粒子的固定化1,4-二氮杂双环[2.2.2]辛烷（DABCO），介绍了一种新型催化剂。对于催化剂的合成，首先通过（3-氯丙基）三甲氧基硅烷对二氧化硅-磁性氧化铁核壳纳米粒子进行功能化。然后，功能化的二氧化硅磁性氧化铁核壳纳米粒子与DABCO反应形成最终催化剂。通过扫描电子显微镜，振动样品磁力计，热重分析，X射线光电子能谱和傅里叶变换红外光谱对催化剂进行了表征。该催化剂用于合成吡喃并[3,2- c：5,6- c'] dichromene-6,8-dione衍生物。使用了几种起始原料，所有这些原料均以高分离产率获得了所需的产物（19个实例）。催化剂在反应中也显示出非常好的可重复使用性。