9,9-dimethyl-12-(4-methoxyphenyl)-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one | 1011735-72-0

• 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: 9,9-dimethyl-12-(4-methoxyphenyl)-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one
• 英文别名: 9,9-dimethyl-12-(4-methoxyphenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one；12-(4-methoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one；9,10-dihydro-9,9-dimethyl-12-(4-methoxyphenyl)-8H-benzo[a]xanthen-11(12H)-one；9,9-dimethyl-12-(4-methoxyphenyl)-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one；12-(4-methoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one；9,9-dimethyl-12-(4-methoxyphenyl)-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one；9,9-Dimethyl-12-(4-methoxyphenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one；12-(4-methoxyphenyl)-9,9-dimethyl-10,12-dihydro-8H-benzo[a]xanthen-11-one
• CAS: 1011735-72-0
• 化学式: C₂₆H₂₄O₃
• 分子量: 384.475
• InChiKey: KWUNEYBBGDQKMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9,9-dimethyl-12-(4-methoxyphenyl)-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以80%的产率得到9,9-dimethyl-12-(4-methoxyphenyl)-8,9,10,12-tetrahydrobenzo[a]xanthene-11-thione
  参考文献：
  名称：

  Synthesis, Spectroscopic Analysis, and In-Vitro Antimicrobial Evaluation of some Tetrahydrobenzo[a]Xanthene-11-Thiones

  摘要：

  A series of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-thiones were synthesized by the reaction of substituted 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones with Lawesson's Reagent in toluene under standard reaction conditions. All synthesized compounds were characterized by IR, NMR (H-1 and C-13), and mass spectra. Moreover, 2D-NMR (HOMOCOSY, HSQC, and HMBC) studies were also performed for compound 10b. The synthesized compounds were also screened for their antibacterial activities. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional figures.]

  DOI：

  10.1080/10426507.2012.757611
• 作为产物：
  描述：

  12-(4-methoxyphenyl)-8,9,10,12-tetrahydro-7aH-naphtho[1,2-e]pyrrolo[2,1-b][1,3]oxazine 在 dipotassium peroxodisulfate 、 copper(II) bis(trifluoromethanesulfonate) 、 silver nitrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.5h， 生成 9,9-dimethyl-12-(4-methoxyphenyl)-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one
  参考文献：
  名称：

  解构环化介导的呫吨衍生物的一锅法合成

  摘要：

  通过解构环化方法在一锅操作下实现了萘嗪直接转化为各种呫吨衍生物。在有氧反应条件下进行连续氧化C(sp 3 )–O/C(sp 3 )–N裂解和分子内/分子间成环反应。对基材进行的机理分析表明，C(sp 3 )-O 键断裂取代了 C(sp 3 )-N 键断裂。通过C(sp 3 )–O裂解原位生成的Betti碱中间体被成功分离。基于分子对接研究，分子间环状产物表现出良好的α-葡萄糖苷酶抑制特性。

  DOI：

  10.1039/d4ob00093e

文献信息

• A novel polymeric catalyst for the one-pot synthesis of xanthene derivatives under solvent-free conditions
  作者：Behrooz Maleki、Shahram Barzegar、Zeinalabedin Sepehr、Mina Kermanian、Reza Tayebee

  DOI：10.1007/s13738-012-0092-5

  日期：2012.10

  simple, efficient, and environmentally benign route was developed for the preparation of 14-aryl or alkyl-14H-dibenzo[a,j]xanthene, 1,8-dioxo-octahydroxanthene and 12-aryl—8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones from condensation of various aldehydes with (i) β-naphthol, (ii) cyclic 1,3-dicarbonyl compounds and (iii) β-naphthol and cyclic 1,3-dicarbonyl compounds, using novel polymeric catalyst [poly(AMPS-co-AA)]

  开发了一种简单，有效且环境友好的方法，用于制备14-芳基或烷基14 H-二苯并[a，j]氧杂蒽，1,8-二氧代-八氢氧杂蒽和12-芳基-8,9,10，各种醛与（i）β-萘酚，（ii）环状1,3-二羰基化合物和（iii）β-萘酚和环状1,3-二羰基化合物缩合而成的12-四氢苯并[a]黄嘌呤-11-酮，在无溶剂条件下使用新型聚合物催化剂[聚（AMPS-co-AA）]。使用容易获得的催化剂，更短的反应时间，更好的产率，反应的简单性，非均相系统和容易的后处理是本方法的优点。
• Rapid, efficient and solvent-free synthesis of (un)symmetrical xanthenes catalyzed by recyclable sulfated polyborate
  作者：Manisha S. Patil、Amey V. Palav、Chetan K. Khatri、Ganesh U. Chaturbhuj

  DOI：10.1016/j.tetlet.2017.06.027

  日期：2017.7

  straightforward approach to the synthesis of 1,8-dioxo-octahydroxanthenes, 14-phenyl-14H-dibenzo[a,j]xanthene and tetrahydrobenzoxanthene-11-ones under solvent-free conditions using sulfated polyborate as a highly efficient catalyst. The procedure offers several advantages including cleaner reaction profile, mild reaction condition, economic, recyclable and environmentally benign catalyst, high yields, simple

  本研究描述了一种在无溶剂条件下使用硫酸盐快速合成1,8-二氧-八氢氧杂蒽，14-苯基-14 H-二苯并[ a，j ]氧杂蒽和四氢苯并氧杂蒽-11的快速，简单和直接的方法。多硼酸盐作为高效催化剂。该方法具有几个优点，包括更清洁的反应曲线，温和的反应条件，经济，可循环使用和对环境无害的催化剂，高收率，简单的实验和后处理程序。尽管非萃取性后处理/纯化以及催化剂的可重复使用性使该方法在经济上可大规模使用。
• 4-Imidazol-1-yl-butane-1-sulfonic acid or a novel liquid salt? The NMR analysis and dual solvent-catalytic efficiency for one-pot synthesis of xanthenes
  作者：Nader Ghaffari Khaligh、Lim Shi Teng、Ong Chiu Ling、Mohd Rafie Johan、Juan Joon Ching

  DOI：10.1016/j.molliq.2019.01.041

  日期：2019.3

  structure of the product was investigated by the NMR analysis in CD3OD and DMSO‑d6. This work demonstrated that 4-imidazol-1-yl-butane-1-sulfonic acid could not be obtained through the above reaction and the mixture of zwitterionic (I) and ionic (II) structure is produced. The structure of the liquid salt (I + II) was characterized and analyzed by 2D NMR. Then, the dual solvent-catalytic efficiency of

  咪唑和1,4-丁烷磺酸等摩尔混合物的反应在90°C下在乙苯中进行12 h，并通过NMR分析在CD 3 OD和DMSO- d 6中研究产物的结构。这项工作表明通过上述反应不能获得4-咪唑-1-基-丁烷-1-磺酸，并且生成了两性离子（I）和离子（II）结构的混合物。通过2D NMR对液态盐（I + II）的结构进行表征和分析。然后，在温和的条件下研究了液态盐（I + II）的双溶剂催化效率，以合成多种黄嘌呤，从而在较短的反应时间内以良好的产率提供了所需的产物。研究了液态盐（I + II）的可回收性，其后三个运行的平均回收率为89％。循环使用的液态盐即使经过3次运行也没有表现出明显的催化活性损失，其结构与新鲜液态盐（I + II）相同。
• Phosphoric acid supported on alumina (H3PO4/Al2O3) as an efficient and reusable catalyst for the one-pot synthesis of benzoxanthene pigments
  作者：Hamid Reza Shaterian、Kobra Azizi、Nafiseh Fahimi

  DOI：10.1007/s11164-013-1047-x

  日期：2014.4

  Phosphoric acid supported on alumina (H3PO4/Al2O3) is an efficient catalyst for the catalytic multi-component condensation reaction and a wide variety of syntheses of benzoxanthene pigments in good yields. The remarkable features of this new procedure are high conversions, shorter reaction times, cleaner reaction, and simple experimental and work-up procedures.

  负载于氧化铝上的磷酸（H3PO4/Al2O3）是一种高效的催化剂，可用于催化多组分缩合反应及一系列在良好产率下合成苯并二氧杂蒽类色素的合成中。该新方法的显著特点包括高转化率、较短的反应时间、更纯净的反应过程及简单易行的实验和后处理步骤。
• Immobilization of Lewis acidic ionic liquid on perlite nanoparticle surfaces as a highly efficient solid acid catalyst for the solvent-free synthesis of xanthene derivatives
  作者：L. Moradi、M. Mirzaei

  DOI：10.1039/c9ra03312b

  日期：——

  modified with Lewis acidic ionic liquid (perlite NP@IL/ZrCl4) through a two step procedure. The prepared solid acid catalyst was characterized by Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX) and thermo gravimetric analysis (TGA). Perlite NP@IL/ZrCl4 was used as a new solid acid, reusable and green

  在这项研究中，珍珠岩纳米粒子通过简单的方法制备，然后通过两步过程用路易斯酸性离子液体（珍珠岩 NP@IL/ZrCl 4 ）进行改性。采用傅里叶变换红外光谱(FTIR)、扫描电子显微镜(SEM)、X射线衍射(XRD)、能量色散X射线光谱(EDX)和热重分析(TGA)对制备的固体酸催化剂进行了表征。珍珠岩 NP@IL/ZrCl 4被用作一种新的固体酸、可重复使用的绿色非均相纳米催化剂，用于一锅法合成呫吨衍生物。使用催化量（0.005 g，0.4 mol%）制备的催化剂在无溶剂条件下合成呫吨，后处理简单，产物收率高至优异。该催化剂的可重复使用性和高效率使该方法对大规模环保操作具有吸引力。