12-(4-hydroxyphenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one | 1171121-19-9

• 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-hydroxyphenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• 英文别名: 12-(4-hydroxyphenyl)-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one
• CAS: 1171121-19-9
• 化学式: C₂₃H₁₈O₃
• 分子量: 342.394
• InChiKey: RYACJVHYCDECRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 、 对羟基苯甲醛 、 2-萘酚 在 O-sulfonated poly(4-vinylpyrrolidonium) chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 0.58h， 以93%的产率得到12-(4-hydroxyphenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
  参考文献：
  名称：

  Introduction of O-sulfonated poly(4-vinylpyrrolidonium) chloride as a polymeric and reusable catalyst for the synthesis of xanthene derivatives

  摘要：

  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。

  DOI：

  10.1039/c4ra04915b

文献信息

• Sonochemical syntheses of xanthene derivatives using zeolite-supported transition metal catalysts in aqueous media
  作者：Kazem D. Safa、Elham Taheri、Maryam Allahvirdinesbat、Aligholi Niaei

  DOI：10.1007/s11164-015-2192-1

  日期：2016.4

  An efficient green method for the syntheses of biologically active xanthene derivatives by use of zeolite-supported transition metal catalysts is described. A Fe-Cu/ZSM-5 heterogeneous catalyst has the highest activity in the one-pot syntheses with a wide range of aldehydes and cyclic 1,3-diketones, under ultrasonic irradiation in water at ambient temperatures. The three-component condensation in the presence of supported metal catalysts is operationally simple, requires no expensive or toxic reagents, and gives high yields in short reaction times.

  描述了一种高效的绿色方法，通过使用分子筛支持的过渡金属催化剂合成生物活性黄烷衍生物。Fe-Cu/ZSM-5杂多催化剂在常温水相超声照射条件下，与多种醛和环状1,3-二酮进行一步合成时表现出最高活性。在支持金属催化剂存在下的三组分缩合反应操作简单，无需昂贵或有毒的试剂，且在短反应时间内能获得高产率。
• 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。
• Multicomponent, solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one derivatives catalysed by cyanuric chloride
  作者：Zhan-Hui Zhang、Peng Zhang、Shu-Hong Yang、Hong-Juan Wang、Jia Deng

  DOI：10.1007/s12039-010-0049-0

  日期：2010.5

  An efficient and direct protocol for the preparation of 12-aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one derivatives employing a three-component one-pot reaction of aryl aldehydes, 2-naphthol and cyclic 1,3-dicarbonyl compounds in the presence of a catalytic amount of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine, TCT) under solvent-free conditions is described. The desired products are obtained

  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。
• Facile and rapid synthesis of divers xanthene derivatives using lanthanum(III) chloride/chloroacetic acid as an efficient and reusable catalytic system under solvent-free conditions
  作者：Behjat Pouramiri、Maryam Shirvani、Kermani Tavakolinejad

  DOI：10.2298/jsc160803034p

  日期：——

  LaCl 3 /ClCH 2 COOH was used as an efficient, and recyclable catalytic system for synthesis of 8H-benzo[a]xanthe, hexahydro-1H-xanthene and pyran-10,12(11H)-dione derivatives via a one-pot three-component reaction of aldehydes, 2-naphthol, and cyclic 1,3-dicarbonyl compounds. The reactions proceeded rapidly at 70 o C under solvent-free conditions and the desired products were obtained in good to excellent

  LaCl 3 / ClCH 2 COOH被用作一种可回收的高效催化体系，用于通过一锅法3合成8H-苯并[a]黄嘌呤，六氢-1H-黄嘌呤和吡喃-10,12（11H）-二酮衍生物醛，2-萘酚和环状1,3-二羰基化合物的双组分反应。该反应在无溶剂条件下于70 o C迅速进行，并以良好至极好的收率获得了所需的产物。
• 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.