12-(3-methoxyphenyl)-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one | 1224601-95-9

• 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-(3-methoxyphenyl)-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one
• 英文别名: 12-(3-methoxyphenyl)-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one；12-(3-Methoxyphenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one；12-(3-methoxyphenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• CAS: 1224601-95-9
• 化学式: C₂₄H₂₀O₃
• 分子量: 356.421
• InChiKey: RKRZMBVSLNHICH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-环己二酮 、 3-甲氧基苯甲醛 、 2-萘酚 在 五氯化铌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以63%的产率得到12-(3-methoxyphenyl)-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

• 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。
• A new strategy for the synthesis of benzoxanthenes catalyzed by proline triflate in water
  作者：Jianjun Li、Lingmei Lu、Weike Su

  DOI：10.1016/j.tetlet.2010.02.149

  日期：2010.5

  Catalyzed by proline triflate, benzoxanthenes were obtained in good yields from the condensation of naphthols, aldehydes, and 1,3-dicarbonyl compounds in water. A possible mechanism of this reaction is proposed.

  在三氟甲磺酸脯氨酸的催化下，萘酚，醛和1,3-二羰基化合物在水中的缩合可得到高收率的苯并氧杂蒽。提出了该反应的可能机理。
• Succinimide-N-sulfonic acid: An efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions
  作者：Farhad Shirini、Nader Ghaffari Khaligh

  DOI：10.1016/j.dyepig.2012.06.022

  日期：2012.12

  A mild, simple and convenient procedure for the synthesis of xanthene derivatives is described via three component condensation of aldehydes with 2-naphthol, 1,3-cyclohexanedione and/or a mixture of 2-naphthol and 1,3-cyclohexanediones using succinimide-N-sulfonic acid as an efficient, cheap and readily synthesis catalyst under solvent-free conditions. The structures of the products were characterized

  通过醛与2-萘酚，1,3-环己二酮和/或2-萘酚和1,3-环己二酮的混合物使用琥珀酰亚胺-N进行三组分缩合，描述了一种温和，简单，方便的合成x吨衍生物的方法。-磺酸在无溶剂条件下作为一种高效，廉价且易于合成的催化剂。产品的结构通过其物理常数，与真实样品的比较以及IR，1 H NMR和13 C NMR光谱进行表征。本方法提供了许多优点，例如高收率，简单的方法，低成本，短的反应时间，无溶剂和温和的反应条件以及使用可重复使用的催化剂。
• Microwave-assisted and scandium triflate catalyzed synthesis of tetrahydrobenzo[a]xanthen-11-ones
  作者：Madharam Sudershan Rao、Bhupender S. Chhikara、Rakesh Tiwari、Amir N. Shirazi、Keykavous Parang、Anil Kumar

  DOI：10.1007/s00706-011-0577-4

  日期：2012.2

  Synthesis of 12-aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-ones was achieved by one-pot condensation of beta-naphthol, substituted benzaldehydes, and 1,3-dicarbonyl compounds catalyzed by Sc(OTf)(3) under microwave irradiation in excellent isolated yields. The catalyst was recycled up to four cycles with no appreciable loss in catalytic activity. The compounds were evaluated for Src kinase activity and anticancer activity.
• Niobium Pentachloride Catalyzed One-Pot Multicomponent Condensation Reaction of β-Naphthol, Aryl Aldehydes and Cyclic 1, 3-Dicarbonyl Compounds
  作者：Mohammad Nasseri、Ali Allahresani、Abbas Esmaeili

  DOI：10.2174/15701786113109990029

  日期：2014.1.31

  Niobium pentachloride catalyzed one-pot multicomponent condensation reaction of β-naphthol, aryl aldehydes and cyclic 1,3-dicarbonyl compounds. Thus, a variety of 8,9,10,12-tetrahydrobenzo[a] xanthen-11-one derivatives were produced in good to excellent yields.

  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。