12-(4-nitrophenyl)-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one | 114382-97-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 12-(4-nitrophenyl)-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one
• 英文别名: 12-(4-nitrophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one；12-(4-Nitrophenyl)-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one
• CAS: 114382-97-7
• 化学式: C₂₃H₁₇NO₄
• 分子量: 371.392
• InChiKey: FXKRMVWLHRMFNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  12-(4-nitrophenyl)-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 1.5h， 以85%的产率得到C₂₃H₁₇NO₃S
  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：

  1,3-环己二酮 、 对硝基苯甲醛 、 2-萘酚 在 五氯化铌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以95%的产率得到12-(4-nitrophenyl)-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one
  参考文献：
  名称：

  Niobium Pentachloride Catalyzed One-Pot Multicomponent Condensation Reaction of β-Naphthol, Aryl Aldehydes and Cyclic 1, 3-Dicarbonyl Compounds

  摘要：

  五氯化铌催化了 β-萘酚、芳基醛和环 1,3-二羰基化合物的单锅多组分缩合反应。因此，以良好至极佳的收率制备出了多种 8、9、10、12-四氢苯并[a] 呫吨-11-酮衍生物。

  DOI：

  10.2174/15701786113109990029

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。
• Xanthenones: calixarenes-catalyzed syntheses, anticancer activity and QSAR studies
  作者：Daniel Leite da Silva、Bruna Silva Terra、Mateus Ribeiro Lage、Ana Lúcia Tasca Góis Ruiz、Cameron Capeletti da Silva、João Ernesto de Carvalho、José Walkimar de Mesquita Carneiro、Felipe Terra Martins、Sergio Antonio Fernades、Ângelo de Fátima

  DOI：10.1039/c4ob02611j

  日期：——

  An efficient method is proposed for obtaining tetrahydrobenzo[a]xanthene-11-ones and tetrahydro-[1,3]-dioxolo[4,5-b]xanthen-9-ones. The method is based on the use of p-sulfonic acid calix[n]arenes as catalysts under solvent-free conditions. The antiproliferative activity of fifty-nine xanthenones against six human cancer cells was studied. The capacity of all compounds to inhibit cancer cell growth

  提出了一种有效的方法来获得四氢苯并[a] x吨-11-酮和四氢-[1,3]-二氧杂环戊[4,5-b]黄嘌呤-9-酮。该方法基于在无溶剂条件下使用对磺酸杯芳烃[n]芳烃作为催化剂。研究了五十九种黄酮酮对六种人类癌细胞的抗增殖活性。所有化合物抑制癌细胞生长的能力取决于细胞的组织学起源。QSAR研究表明，在衍生自β-萘酚的化合物中，最有效的抗神经胶质瘤（U251）和肾（NCI-H460）癌细胞的化合物是具有较高氢键供体能力的化合物。
• 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。
• A Simple and Green Approach for the Synthesis of Tetrahydrobenzo[a]-xanthen-11-one Derivatives Using Tetrabutyl Ammonium Fluoride in Water
  作者：Ching-Fa Yao、Shijay Gao、Chen Tsai

  DOI：10.1055/s-0028-1088214

  日期：2009.4

  An efficient and simple procedure for the synthesis of 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives has been described. This one-pot multicomponent reaction involves the reaction of aldehydes, 2-naphthol, and cyclic 1,3-diketones in the presence of catalytic amount of recyclable TBAF in water.

  已描述一种高效简单的合成12-芳基或12-烷基-8,9,10,12-四氢苯并[a]荧蒽-11-酮衍生物的程序。这种“一锅法”多组分反应涉及在可回收的催化剂TBAF（四丁基氟化铵）存在下，用水作为溶剂，反应醛、2-萘酚和环状1,3-二酮。
• A novel method for the synthesis of tetrahydrobenzo[a]-xanthen-11-one derivatives using cerium(III) chloride as a highly efficient catalyst
  作者：Mazaahir Kidwai、Anwar Jahan、Neeraj Kumar Mishra

  DOI：10.1016/j.crci.2012.01.002

  日期：2012.4

  Résumé Cerium(III) chloride is found to be an highly efficient catalyst for the addition of aldehydes, β-naphthol and cyclic 1,3-dicarbonyl compounds/Meldrum's acid via a multicomponent reaction. The easy availability of starting materials, novel and eco-friendly procedure makes this strategy more useful for the preparation of tetrahydrobenzo[a]-xanthen-11-one, and benzo[f]chromen-3-one derivatives.

  摘要 氯化铈(III)被发现是一种高效的催化剂，可通过多组分反应促进醛、β-萘酚和环状1,3-二酮化合物/梅尔德朗酸的加成。起始材料易于获取，工艺新颖且环保，使得这种策略在制备四氢苯并[a]喹啉-11-酮和苯并[f]色烯-3-酮衍生物方面更加实用。