10,10-dimethyl-7-phenyl-10,11-dihydro-7H-benzo[c]xanthen-8(9H)-one | 1224601-83-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 10,10-dimethyl-7-phenyl-10,11-dihydro-7H-benzo[c]xanthen-8(9H)-one
• 英文别名: 10,10-Dimethyl-7-phenyl-10,11-dihydro-7h-benzo[c]xanthen-8(9h)-one；10,10-dimethyl-7-phenyl-9,11-dihydro-7H-naphtho[1,2-b]chromen-8-one
• CAS: 1224601-83-5
• 化学式: C₂₅H₂₂O₂
• 分子量: 354.448
• InChiKey: OIMPYZBJIJSTPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  萘酚 、 苯甲醛 、 5,5-二甲基-1,3-环己二酮 在 tetrabutylammonium prolinate ionic liquid(at)(CH₂)3Si(at)silica nanoparticles 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 以82%的产率得到10,10-dimethyl-7-phenyl-10,11-dihydro-7H-benzo[c]xanthen-8(9H)-one
  参考文献：
  名称：

  高效可重复使用的TBAPIL@Si(CH2)3@nano-silica基纳米催化剂制备苯并氧杂蒽衍生物的制备及应用

  摘要：

  制备脯氨酸四丁基铵离子液体（TBAPIL），合成介孔二氧化硅纳米粒子（NPs）。这两者通过丙基三乙氧基硅烷连接以制备可重复使用的催化剂TBAPIL@Si(CH 2 ) 3@silica NPs (TBAPILS)。通过傅里叶变换红外光谱 (FT-IR) 和核磁共振 (NMR) 分析检查 TBAPIL 的形成。X 射线衍射分析证实了二氧化硅 NPs 的结构和 TBPAIL 在其上的连接。透射电子显微镜证明了二氧化硅纳米粒子的蓬勃发展。扫描电子显微镜图揭示了二氧化硅 NPs 和 TBAPILS 的形态变化。FT-IR 分析也证实了 TBAPILS 催化剂的形成。此外，还检查了 TBAPILS 在合成四氢苯并氧杂蒽-11-酮的各种衍生物方面的有效性。所得化合物的形成和结构经FT-IR、元素分析、1 HNMR和13C NMR光谱分析。发现催化剂 TBAPILS 可以成功使用多达五个循环而没有显着的活性损失。

  DOI：

  10.1007/s13738-021-02211-1

文献信息

• A new strategy for the synthesis of benzoxanthenes catalyzed by proline triflate in water
  作者：Jianjun Li、Lingmei Lu、Weike Su

  DOI：10.1016/j.tetlet.2010.02.149

  日期：2010.5

  Catalyzed by proline triflate, benzoxanthenes were obtained in good yields from the condensation of naphthols, aldehydes, and 1,3-dicarbonyl compounds in water. A possible mechanism of this reaction is proposed.

  在三氟甲磺酸脯氨酸的催化下，萘酚，醛和1,3-二羰基化合物在水中的缩合可得到高收率的苯并氧杂蒽。提出了该反应的可能机理。
• Pentafluorophenylammonium Triflate (PFPAT): An Efficient, Practical, and Cost-Effective Catalyst for One-Pot Condensation of β-Naphthol, Aldehydes and Cyclic 1,3-Dicarbonyl Compounds
  作者：Samad Khaksar、Nosratollah Behzadi

  DOI：10.2174/138620712803901153

  日期：2012.11.7

  A pentafluorophenylammonium triflate (PFPAT) catalyst (10 mol%) efficiently promoted one-pot condensation of β-naphthol, aldehydes, and cyclic 1,3-dicarbonyl compounds in good to excellent yield under mild reaction conditions. These catalytic condensations have advantages from the viewpoint of green chemistry. PFPAT organocatalyst is air-stable, cost-effective, easy to handle, and easily removed from

  在轻度的反应条件下，五氟苯基三氟甲磺酸铵（PFPAT）催化剂（10 mol％）有效地促进了β-萘酚，醛和环状1,3-二羰基化合物的一锅缩合。从绿色化学的观点来看，这些催化缩合具有优点。PFPAT有机催化剂是空气稳定的，具有成本效益的，易于处理的，并且易于从反应混合物中除去。
• Eco-friendly synthesis of tetrahydrobenzo[c]xanthenes catalyzed by functional ionic liquid in water
  作者：Jiaojiao Yang、Jinming Yang、Ting Zhu、Pingping Wang、Dong Fang

  DOI：10.1007/s00706-013-1057-9

  日期：2013.11

  AbstractA clean procedure for the synthesis of tetrahydrobenzo[c]xanthenes was established in the presence of a functional ionic liquid, 1-butyl-(4-dimethylamino)pyridinium hydroxide [BDMAP][OH]. The reaction was carried out via the one-pot multi-component condensation of aromatic aldehydes, cyclic 1,3-dicarbonyl compounds, and α-naphthol in aqueous media, to afford good to excellent yields ranging

  摘要在功能性离子液体1-丁基-（4-二甲基氨基）吡啶鎓氢氧化物[BDMAP] [OH]存在下，建立了合成四氢苯并[ c ]黄嘌呤的清洁方法。该反应是通过在水性介质中一锅法将芳族醛，环状1,3-二羰基化合物和α-萘酚进行多组分缩合来实现的，在60-90范围内，产率从80％到85％不等。分钟 反应后，催化剂可以循环使用几次，而催化活性没有明显降低。 图形概要
• Magnetite-Containing Sulfonated Polyacrylamide as a Nanocatalyst for the Preparation of Biscoumarins
  作者：Kaveh Parvanak Boroujeni、Shahla Hadizadeh、Sodabeh Hasani、Abdulhamid Fadavi、Mansooreh Shahrokh

  DOI：10.17344/acsi.2017.3437

  日期：2017.9.10

  Magnetite-containing sulfonated polyacrylamide was easily prepared through polymerization of the corresponding monomers followed by the reaction with Fe3O4 nanoparticles. The characterization of the obtained catalyst was performed by Fourier transform infrared spectroscopy (FT-IR), thermal gravimetric analysis (TGA), scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), X-ray diffraction (XRD), and vibrating sample magnetometer (VSM). The acidic SO3H moiety was found to be 1.1 mmol per gram of the obtained polymer. The catalytic activity of the polymer was examined for the synthesis of biscoumarin derivatives by two-component one-pot domino Knoevenagel-type condensation/Michael reaction between aldehydes and 4-hydroxycoumarin. Biscoumarins were obtained in high to excellent yields in short time. The work-up procedure of this reaction was very simple. The catalyst is stable (as a bench top catalyst) with easy-handling and it can be used again.
• A multicomponent, solvent-free, one-pot synthesis of benzoxanthenones catalyzed by HY zeolite: their anti-microbial and cell imaging studies
  作者：Velladurai Rama、Kuppusamy Kanagaraj、Kasi Pitchumani

  DOI：10.1016/j.tetlet.2011.10.143

  日期：2012.2

  An atom-economical, multicomponent condensation of naphthols, aldehydes, and cyclic 1,3-dicarbonyl compounds catalyzed by HY zeolites under solvent-free conditions is reported. This ecofriendly protocol offers several advantages such as a green and cost-effective procedure with excellent yield, shorter reaction time, simpler work-up, recovery, and reusability of metal-free solid acid heterogeneous catalyst and tolerance of a wide range of functional groups. The biological studies such as in vitro anti-microbial activities of the prepared new compounds and cell imaging studies on K562 leukemia cell lines by selected benzoxanthenones are evaluated. (C) 2011 Elsevier Ltd. All rights reserved.