12-(2-methoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one | 1187642-03-0

• 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: 12-(2-methoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• 英文别名: 9,9-dimethyl-12-(2-methoxyphenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one；9,9-dimethyl-12-(2-methoxyphenyl)-8,9,10,12-tetrahydrobenzo[α]xanthen-11-one；12-(2-methoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one；9,9-dimethyl-12-(2-methoxyphenyl)-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one；9,10-dihydro-12-(2-methoxyphenyl)-9,9-dimethyl-8H-benzo[a]xanthen-11(12H)-one；12-(2-methoxyphenyl)-9,9-dimethyl-10,12-dihydro-8H-benzo[a]xanthen-11-one
• CAS: 1187642-03-0
• 化学式: C₂₆H₂₄O₃
• 分子量: 384.475
• InChiKey: LUQPGMUCQDGYBN-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：

  12-(2-methoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 0.67h， 以77%的产率得到12-(2-methoxyphenyl)-9,9-dimethyl-10,12-dihydro-8H-benzo[a]xanthene-11-thione
  参考文献：
  名称：

  Synthesis of novel 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-thiones and evaluation of their biocidal effects

  摘要：

  Novel 12-aryl-8,9,10,12-tetrahydrobenzolakanthene-11-thiones have been synthesized in high yields by treatment of the corresponding oxo analogs with Lawesson's reagent. The structure has been confirmed by X-ray analysis. The compounds were tested for in vitro antifungal activity against Rhizoctonia bataticola, Sclerotium rolfsii, Fusarium oxysporum and Alternaria porii. The compounds exhibited moderate to good activity against all pathogens. Insecticidal activity of these compounds against Spodoptera litura was observed to be comparable to commercial pyrethroid insecticide, cypermethrin. The urease inhibitory activity has also been studied. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.025
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 邻甲氧基苯甲醛 、 2-萘酚 在 4-十二烷基苯磺酸 作用下， 以 水 为溶剂， 反应 2.0h， 以90%的产率得到12-(2-methoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
  参考文献：
  名称：

  12-Aryl-8,9,10,12-四氢苯并[a]xanthen-11-one衍生物在水介质中超声催化对十二烷基苯磺酸的催化合成

  摘要：

  摘要 通过芳香醛、2-萘酚和 5,5-二甲基-1 的三组分缩合有效合成 12-芳基-8,9,10,12-四氢苯并[a]xanthen-11-one 衍生物， 3-环己二酮在 40-42°C 下以 76-93% 的产率在超声波照射下使用对十二烷基苯磺酸作为催化剂在水介质中进行。图形概要

  DOI：

  10.1080/00397911.2011.555048

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。
• Introduction of O-sulfonated poly(4-vinylpyrrolidonium) chloride as a polymeric and reusable catalyst for the synthesis of xanthene derivatives
  作者：Farhad Shirini、Peyman Najafi Moghadam、Simin Moayedi、Mohadeseh Seddighi

  DOI：10.1039/c4ra04915b

  日期：——

  O-Sulfonated poly(4-vinylpyrrolidonium) chloride is prepared from the reaction of poly(4-vinylpyrrolidone) [PVP], as a cheap and commercially available reagent, and neat chlorosulfonic acid at room temperature. A variety of techniques including infrared spectra (IR), thermal gravimetric analysis (TGA), scanning electron microscopy (SEM), X-ray diffraction (XRD), pH analysis and Hammett acidity (Ho) were used to characterize this solid acid. This polymeric reagent showed excellent catalytic activity for the synthesis of xanthene derivatives including 1,8-dioxooctahydroxanthenes, 14-aryl-14H-dibenzo[a,j] xanthenes and 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones under solvent free conditions. The products were formed in excellent yields over short reaction times and the catalyst can be reused several times without any appreciable loss in its activity.

  采用廉价的市售试剂聚(4-乙烯基吡咯烷酮)[PVP]和纯氯磺酸在室温下反应制备了O-磺化聚(4-乙烯基吡咯烷酮-氯)。通过红外光谱(IR)、热重分析(TGA)、扫描电子显微镜(SEM)、X射线衍射(XRD)、pH分析和Hammett酸性(Ho)等多种技术对这种固体酸进行了表征。这种聚合物试剂在无溶剂条件下对制备包括1,8-二氧杂八氢吖啶、14-芳基-14H-二苯并[a,j]吖啶和12-芳基-8,9,10,12-四氢苯并[a]吖啶-11-酮在内的吖啶衍生物表现出优异的催化活性。产物的产率很高，反应时间短，催化剂可以重复使用多次而不会明显降低其活性。
• Glycine as a Green Catalyst for the Preparation of Xanthenes
  作者：Farzaneh Mohamadpour

  DOI：10.1080/00304948.2020.1834343

  日期：2021.1.2

  (2021). Glycine as a Green Catalyst for the Preparation of Xanthenes. Organic Preparations and Procedures International: Vol. 53, No. 1, pp. 59-67.

  （2021年）。甘氨酸作为制备黄嘌呤的绿色催化剂。国际有机制剂和程序：第 53，第1号，第59-67页。
• Synthesis of the nano-magnetic ionic liquid based on caffeine and its catalytic application in the synthesis of xanthenes
  作者：Masoumeh Salami、Ali Ezabadi

  DOI：10.1007/s11164-020-04224-6

  日期：2020.10

  In this research, a novel nano-sized cube-shaped magnetic ionic liquid based on caffeine was synthesized and characterized by various spectroscopic and analytical techniques including Fourier transform infrared spectroscopy, Raman spectroscopy, proton NMR (1H NMR), carbon-13 NMR (13C NMR), mass spectroscopy, thermal gravimetric analysis/differential thermal gravimetric analysis, elemental analysis

  在这项研究中，合成了一种新型的基于咖啡因的纳米级立方体形离子液体，并通过多种光谱和分析技术进行了表征，包括傅立叶变换红外光谱，拉曼光谱，质子NMR（1 H NMR），碳13 NMR（13 C NMR），质谱，热重分析/微分热重分析，元素分析，电感耦合等离子体分析，X射线衍射，能量色散X射线分析，场发射扫描电子显微镜和振动样品磁力计。在无溶剂条件下合成各种黄嘌呤时，纳米磁性IL表现出卓越的催化活性。
• Sulfonation of carbonized xylan-type hemicellulose: a renewable and effective biomass-based biocatalyst for the synthesis of O- and N-heterocycles
  作者：Jiliang Ma、Xinwen Peng、Linxin Zhong、Runcang Sun

  DOI：10.1039/c8nj01329b

  日期：——

  application of biomass-based carbonaceous solid acids in catalysis is attracting increasing attention in the field of chemistry. In this study, a heterogeneous carbon-based solid acid biocatalyst (CXH-SO3H) with regular spherical structure was synthesized from xylan-type hemicellulose (XH) by a simple two-step method. The catalyst was successfully applied in the synthesis of O- and N-heterocycles with yields

  基于生物质的碳质固体酸在催化中的应用在化学领域引起了越来越多的关注。在这项研究中，通过简单的两步法从木聚糖型半纤维素（XH）合成具有规则球形结构的异质碳基固体酸生物催化剂（CXH-SO 3 H）。该催化剂已成功用于O和N杂环的合成，产率分别为80-99％和60-97％。鉴于环境和经济，CXH-SO 3H显示出环境友好，易于操作，后处理简单，优异的产率以及避免使用有机溶剂和昂贵的催化剂的优点。此外，所合成的固体酸催化剂可以使用数个循环而不会显着降低其催化活性。FT-IR，XRD和SEM的结果表明，在CXH-SO 3 H的理化结构上没有观察到明显的差异。因此，环保型CXH-SO 3 H催化剂是从低成本原料绿色合成O和N杂环的有前途的候选者，在部分替代可商购的固体和液体酸催化剂和贵金属方面具有良好的前景。催化剂。