12-(4-bromophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one | 1219810-73-7

• 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-(4-bromophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• 英文别名: 12-(4-Bromophenyl)-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one
• CAS: 1219810-73-7
• 化学式: C₂₃H₁₇BrO₂
• 分子量: 405.291
• InChiKey: IDUROBSVORFXON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 、 对溴苯甲醛 、 2-萘酚 在 三聚氯氰 作用下， 反应 0.5h， 以90%的产率得到12-(4-bromophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
  参考文献：
  名称：

  氰尿酰氯催化的多组分无溶剂合成12-芳基8,9,10,12-四氢苯并[a]-黄嘌呤-11-one衍生物

  摘要：

  利用芳基醛，2-萘酚和三酚的三组分一锅法反应制备12-芳基-8,9,10,12-四氢-苯并[ a ]黄原-11-酮衍生物的有效直接方法描述了在无溶剂条件下催化量的氰尿酰氯（2,4,6-三氯-1,3,5-三嗪，TCT）存在下的环状1,3-二羰基化合物。以高收率和短反应时间获得所需产物。

  DOI：

  10.1007/s12039-010-0049-0

文献信息

• 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。
• 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。
• One-Pot, Three-Component Condensation of Aldehydes, 2-Naphthol and 1,3-Dicarbonyl Compounds
  作者：Li-Ping Mo、Hong-Li Chen

  DOI：10.1002/jccs.201000025

  日期：2010.4

  A practical and efficient procedure for the one‐pot multicomponent couping of aryl aldehydes, 2‐naphthol and cyclic 1,3‐dicarbonyl compounds using perchloric acid adsorbed on silica gel (HClO4‐SiO2) as a highly efficient, inexpensive, convenient, reusable heterogeneous catalyst under solvent‐free conditions has been developed. Various biologically important 12‐aryl‐8,9,10,12‐tetrahydrobenzo[a]xanthen‐11‐one

  一种实用高效的方法，可通过吸附在硅胶上的高氯酸（HClO 4 -SiO 2）作为芳烃醛，2-萘酚和环状1,3-二羰基化合物的单锅多组分偶合，高效，廉价，方便，已开发出在无溶剂条件下可重复使用的多相催化剂。各种具有生物学重要意义的12-芳基-8,9,10,12-四氢苯并[ a ]黄嘌呤-11-one衍生物均已高效合成，收率很高。本方法具有许多优点，例如反应时间短，后处理简单，产率高，成本低以及反应条件温和。此外，该催化剂可以简单地回收和再利用而不会明显损失其催化活性。
• Triphenylphosphine-m-sulfonate/carbon tetrabromide as an easily recoverable catalyst system for the efficient synthesis of xanthene and xanthenone derivatives under solvent-free conditions
  作者：Cong-De Huo、Xia-Zhen Bao、Dong-Cheng Hu、Xiao-Dong Jia、Chou-Gu Sun、Cheng Wang

  DOI：10.1016/j.cclet.2014.01.023

  日期：2014.5

  Abstract A solid complex, readily prepared from commercially available sodium triphenylphosphine- m -sulfonate (TPPMS) and carbon tetrabromide, can be used as an easily recoverable and reusable catalyst system for one-pot condensation of 2-naphthol with aldehydes to construct 14-aryl(alkyl)-14 H -dibenzo[ a , j ]xanthene derivatives and one-pot condensation of 2-naphthol with aldehydes and cyclic 1

  摘要由市售的三苯基膦-间磺酸钠（TPPMS）和四溴化碳易于制备的固体配合物，可作为易于回收和重复使用的催化剂体系，用于2-萘酚与醛的一锅缩合以构建14-芳基（烷基）-14 H-二苯并[a，j]氧杂蒽衍生物和2-萘酚与醛和环状1,3-二羰基化合物的一锅缩合反应，以构建12-芳基（烷基）-8,9,10,12 -四氢苯并[a]黄酮-11-酮衍生物。
• Nano-WO 3 -supported sulfonic acid: New, efficient and high reusable heterogeneous nano catalyst
  作者：Ali Amoozadeh、Salman Rahmani

  DOI：10.1016/j.molcata.2014.09.020

  日期：2015.1

  Nano-WO3-supported sulfonic acid [n-WO3-SO3H (n-WSA)] is easily prepared from the reaction of nano WO3 with chlorosulfonic acid as sulfonating agent. This new catalyst is characterized by X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), FT-IR spectroscopy, thermal gravimetric analysis (TGA), pH analysis and Hammett acidity function. Nano-WO3-supported sulfonic acid is used as an efficient and recyclable catalyst for some organic reactions such as synthesis of 1,8-dioxo-octahydroxanthene, tetrahydrobenzoxanthene and benzimidazolo quinazolinone derivatives. All of the reactions are very fast and the yields are excellent. The used catalyst was easily separated and reused for 10 runs without appreciable loss of its catalytic activity. (C) 2014 Elsevier B.V. All rights reserved.