5-benzo[d][1,3]dioxole-14H-dibenzo[a,j]xanthene | 37097-04-4

• 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: 5-benzo[d][1,3]dioxole-14H-dibenzo[a,j]xanthene
• 英文别名: 9-(3',4'-Methylendioxyphenyl)dibenzoxanthen；14-benzo[1,3]dioxol-5-yl-14H-dibenzo[a,j]xanthene；14-Benzo[1,3]dioxol-5-yl-14H-dibenzo[a,j]xanthen；2-(1,3-benzodioxol-5-yl)-13-oxapentacyclo[12.8.0.03,12.04,9.017,22]docosa-1(14),3(12),4,6,8,10,15,17,19,21-decaene
• CAS: 37097-04-4
• 化学式: C₂₈H₁₈O₃
• 分子量: 402.449
• InChiKey: NXHNQAUCHBNEHP-UHFFFAOYSA-N

物化性质

• 熔点：
  240-241 °C(Solvent: Dimethylformamide ; Ethanol)
• 沸点：
  569.5±50.0 °C(Predicted)
• 密度：
  1.338±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  胡椒醛 、 2-萘酚 在 indium(III) triflate 作用下， 以 水 为溶剂， 反应 9.0h， 以90%的产率得到5-benzo[d][1,3]dioxole-14H-dibenzo[a,j]xanthene
  参考文献：
  名称：

  三氟甲磺酸铟催化一锅法合成14-烷基或芳基-14H-二苯并[a, j]呫吨在水中

  摘要：

  已开发出一种温和、高效且环境友好的方法，用于在催化量的铟 (III) 存在下，通过 2-萘酚和醛缩合合成 14-烷基或芳基-14H-二苯并[a, j] 呫吨。 ) 三氟甲磺酸酯 (2 mol%) 在 100°C 的水中。反应中使用了不同类型的芳香族和脂肪族醛，并且在所有情况下都以中等至极好的收率合成了产物。© 2009 Wiley Periodicals, Inc. 杂原子化学 20:232–234, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20539

  DOI：

  10.1002/hc.20539

文献信息

• Yb(OTf)3 catalyzed condensation reaction of β-naphthol and aldehyde in ionic liquids: a green synthesis of aryl-14H-dibenzo[a,j]xanthenes
  作者：Weike Su、Dong Yang、Can Jin、Bo Zhang

  DOI：10.1016/j.tetlet.2008.03.124

  日期：2008.5

  A facile, efficient and green synthesis of aryl-14H-dibenzo[a,j]xanthenes has been developed by one-pot condensation of β-naphthol and substituted benzaldehydes in the presence of ytterbium triflates in ionic liquids.

  在离子液体中，在tri三氟es存在下，通过一锅缩合β-萘酚和取代的苯甲醛，已经开发了一种简便，高效且绿色的芳基14 H-二苯并[ a，j ]蒽酮。
• Synthesis of 14-aryl-14<i>H</i>-dibenzo[<i>a,j</i>]xanthene Derivatives Catalysed by Expanded Graphite under Solvent-Free Condition
  作者：Geng-Chen Li

  DOI：10.3184/030823408x340771

  日期：2008.8

  A convenient eco-friendly procedure has been developed for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives by one-pot condensation of 2-naphthol and aryl aldehydes catalysed by expanded graphite under solvent-free conditions. The present methodology offers several advantages such as excellent yields, shorter reaction times, low cost and reusability of the catalyst.

  已经开发了一种方便的环保程序，用于在无溶剂条件下通过膨胀石墨催化的 2-萘酚和芳基醛的一锅缩合合成 14-芳基-14H-二苯并[a,j] 呫吨衍生物。本方法提供了几个优点，例如优异的产率、更短的反应时间、低成本和催化剂的可重复使用性。
• Synthesis and Luminescence of 14-Aryl- or Alkyl-14<i>H</i>-dibenzo[<i>a,j</i>]xanthenes Catalyzed by 2-1′-Methylimidazolium-3-yl-1-ethyl Sulfate
  作者：Hui Wu、Xiu-Mei Chen、Yu Wan、Hai-Qiang Xin、Hua-Hong Xu、Cai-Hui Yue、Li-Ling Pang、Rui Ma

  DOI：10.1080/00397910902838854

  日期：2009.10.12

  A facile and efficient synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes has been accomplished by treatment of -naphthol with aryl or alkyl aldehydes catalyzed by 2-1'-methylimidazolium-3-yl-1-ethyl sulfate in ionic liquid [BMIM][BF4] at 80 degrees C. The luminescence of products was studied in detail.
• Synthesis and in vitro study of 14-aryl-14H-dibenzo[a.j]xanthenes as cytotoxic agents
  作者：Asish K. Bhattacharya、Kalpeshkumar C. Rana、Mohammad Mujahid、Irum Sehar、Ajit K. Saxena

  DOI：10.1016/j.bmcl.2009.08.033

  日期：2009.10

  A simple and expedient method for the synthesis of a series of 14-aryl-14H-dibenzo[a.j]xanthenes is described through a one-pot condensation of beta-naphthol with aryl aldehydes catalysed by TaCl(5) under solvent-free conventional heating. The major advantages of the present method are: high yields, less reaction time, solvent-free condition and easy purification of the products. The synthesized 14-aryl-14H-dibenzo[a.j]xanthenes were evaluated against a panel of six human cancer lines of different tissues. Synthesized compound 30 showed IC(50) of 37.9 and 41.3 mu M against Colo-205 and 502713, respectively, whereas 3g showed IC(50) of 41.9 mu M against Colo-205. (C) 2009 Elsevier Ltd. All rights reserved.
• Silica sulfuric acid: A simple, efficient, and reusable heterogeneous catalyst for the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes under conventional heating and solvent-free conditions
  作者：Raveendra K. Hunnur、B. Sunilkumar、P. S. Kumar、N. Srinivasulu、R. H. Udupi、V. Hima bindu

  DOI：10.1007/s10593-008-0035-3

  日期：2008.2

  A novel approach towards the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes is described from a known reaction between substituted aldehydes and beta-naphthol in the presence of heterogeneous catalyst silica sulfuric acid under conventional heating as well as solvent-free conditions to afford good to excellent yields. The catalyst is reusable; it can be used several times without any decrease in the product yield.