9-<2-Chlor-phenyl>-1.2-benzo-5.6.7.8-tetrahydro-xanthenon-(8) | 114382-95-5

• 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: 9-<2-Chlor-phenyl>-1.2-benzo-5.6.7.8-tetrahydro-xanthenon-(8)
• 英文别名: 12-(2-chlorophenyl)-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one；12-(2-chlorophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
• CAS: 114382-95-5
• 化学式: C₂₃H₁₇ClO₂
• 分子量: 360.84
• InChiKey: XBKJDWWJJHLEJZ-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

• 作为反应物：
  描述：

  9-<2-Chlor-phenyl>-1.2-benzo-5.6.7.8-tetrahydro-xanthenon-(8) 、 氨基硫脲 在 溶剂黄146 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 24.0h， 以65%的产率得到12-(2-chlorophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one thiosemicarbazone
  参考文献：
  名称：

  NMR spectral and structural studies on some xanthenones and their thiosemicarbazone derivatives: Crystal and molecular structure of 12-(2-chlorophenyl)-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one

  摘要：

  A series of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones [1a-9a] were prepared employing a three component one-pot reaction of aryl aldehyde, 2-naphthol and 1,3-cyclohexanedione using BF3 center dot OEt2 as catalyst. Thiosemicarbazone derivatives [1b-5b] were also prepared in the presence of acid catalyst. All the synthesized compounds have been characterized by IR and NMR. The structure of 5b was confirmed by HSQC spectral analysis. Single crystal X-ray structural analysis of 12-(2-chloropheny1)8,9,10,12-tetrahydrobenzo[a]xanthen-11-one evidences the envelope and flattened-boat conformations of cyclohexenone and pyran rings respectively. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.11.003
• 作为产物：
  描述：

  2-氯苯甲醛 、 1,3-环己二酮 、 2-萘酚 在 甲烷磺酸 作用下， 以 neat (no solvent) 为溶剂， 反应 0.67h， 以87%的产率得到9-<2-Chlor-phenyl>-1.2-benzo-5.6.7.8-tetrahydro-xanthenon-(8)
  参考文献：
  名称：

  甲磺酸催化一锅合成12-芳基或12-烷基-8,9,10,12-四氢苯并[a]黄嘌呤-11-酮衍生物

  摘要：

  在无溶剂条件下，通过一锅法醛，2-萘酚，2-萘酚的缩合反应，已开发出有效合成12-芳基或12-烷基-8,9,10,12-四氢苯并[ a ]黄嘌呤-11-one衍生物的方法。和环状1,3-二羰基化合物在催化量的甲磺酸存在下 该方案具有条件温和，反应时间短，产率高和操作简单的优点。

  DOI：

  10.1002/jhet.882

文献信息

• 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。
• Niobium Pentachloride Catalyzed One-Pot Multicomponent Condensation Reaction of &amp;#946;-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。
• 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.
• 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.
• Manganese Perchlorate–Catalyzed Greener Synthesis of 12-Aryl or 12-Alkyl-8,9,10,12-tetrahydrobenzo[<font>α</font>]xanthen-11-one Derivatives Under Ultrasonication
  作者：Bhupinder Kaur、Anupama Parmar、Harish Kumar

  DOI：10.1080/00397911.2010.525677

  日期：2012.2.1

  A greener and more efficient protocol for the synthesis of 12-aryl or 12-alkyl-8,9,10,12-tetrahydrobenzo[alpha]xanthen-11-one derivatives has been developed via one-pot, three-component reaction of aromatic aldehydes, 2-naphthol, and 1,3-cyclohexadione or 5,5-dimethyl 1,3-cyclohexadione using manganese perchlorate hydrate as a catalyst under ultrasonic irradiation. Good yield, shorter reaction time, simple workup procedure, and milder reaction conditions make this protocol efficient and environmentally benign.