14-(3,4,5-trimethoxyphenyl)-14H-dibenzo[a,j]xanthene | 58162-90-6

• 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: 14-(3,4,5-trimethoxyphenyl)-14H-dibenzo[a,j]xanthene
• 英文别名: 2-(3,4,5-Trimethoxyphenyl)-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: 58162-90-6
• 化学式: C₃₀H₂₄O₄
• 分子量: 448.518
• InChiKey: LZGQOODZYBGIGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 2-萘酚 在 boron sulfonic acid 作用下， 反应 0.42h， 以85%的产率得到14-(3,4,5-trimethoxyphenyl)-14H-dibenzo[a,j]xanthene
  参考文献：
  名称：

  在无溶剂条件下使用硼磺酸作为固体多相催化剂高效地一锅合成x吨衍生物

  摘要：

  摘要 介绍了一种在硼磺酸（B（HSO 4）3）存在下通过一锅缩合醛，2-萘酚和二甲酮/萘酚合成生物活性x吨​​衍生物的高效，便捷和绿色方法。）作为高效多相可重复使用的固体酸催化剂，在无溶剂条件下具有良好至优异的收率。反应中使用了不同类型的芳香族和脂肪族醛，并且在所有情况下均成功合成了产物。另外，短的反应时间，简单的方法，无毒和催化剂的可重复使用性是本方法的其他值得注意的优点。 图形概要

  DOI：

  10.1007/s11164-014-1537-5

文献信息

• Metal free Lewis acid promoted one-pot synthesis of 14-aryl-14H dibenzo [a,j] xanthenes and their simple biological evolution
  作者：Uppalaiah Kusampally、Ramakanth Pagadala、Chinna Rajanna Kamatala

  DOI：10.1016/j.tetlet.2017.07.037

  日期：2017.8

  A green, competent one-pot synthesis of 14-aryl 14H-dibenzo [a,j] xanthene and its bio-computational studies are reported. Target compounds are prepared by the condensation of 2-naphthol with benzaldehyde and its substituents using metal free benzyltrimethylammonium tribromide (BTMA-Br3) catalyst under solvent free thermal and microwave conditions. This technique has more advantages such as high yield

  报道了绿色的，能胜任的一锅合成14-芳基14 H-二苯并[ a，j ]氧杂蒽及其生物计算研究。使用无金属苄基三甲基三溴化铵（BTMA-Br 3）催化剂，在无溶剂的热和微波条件下，通过将2-萘酚与苯甲醛及其取代基缩合来制备目标化合物。该技术具有更多的优点，例如高收率，清洁的过程，低的反应时间，简单的后处理和温和的路易斯有机酸催化剂。
• Crystallography and computational electronic structure investigations on 14-(3, 4, 5-trimethoxyphenyl)-14H-dibenzo[a,j]xanthene
  作者：Karnambaram Anandhan、Maria Susai Boobalan、Perumal Venkatesan、Andivelu Ilangovan、Mahabir Prasad Kaushik、Chidambaram Arunagiri

  DOI：10.1016/j.molstruc.2015.05.025

  日期：2015.10

  found to be, a = 13.9419(2) A, b = 14.1503(2) A, c = 20.2765(3) A, α = 85.892(1)°, β = 87.098(1)°, γ = 61.487(1)°, V = 3505.36(9), Z = 6 respectively. Three symmetrically independent DBX molecules were present in the asymmetric unit. The structural superimposition study shows that the molecule A and B in same conformation, whereas molecule C in opposite conformation. The pyran ring in xanthene core is almost

  摘要 本研究对14-(3, 4, 5-三甲氧基苯基)-14 H-二苯并[ a , j ]呫吨(DBX)的晶体结构和Hirshfeld表面分析进行了研究和报道。DBX 被确定为具有 P-1 空间群的三斜系统。发现的晶胞参数是，a = 13.9419(2) A, b = 14.1503(2) A, c = 20.2765(3) A, α = 85.892(1)°, β = 87.098(1)°, γ = 61.487(1)°，V = 3505.36(9)，Z = 6。不对称单元中存在三个对称独立的 DBX 分子。结构叠加研究表明分子A和B的构象相同，而分子C的构象相反。呫吨核中的吡喃环几乎垂直于3,4,5-三甲氧基苯基取代基的吡喃环。类似地，分子A、B和C中呫吨核的相同吡喃环以船形构象排列。固态结构已通过弱的 C–H⋯O 和 C–H⋯π 相互作用稳定下来。二维指纹图的 Hirshfeld 表面分析表明
• Das, Biswanath; Paidipala, Humani; Nagendra, Siddavatam, Indian Journal of Heterocyclic Chemistry, 2011, vol. 21, # 1, p. 9 - 12
  作者：Das, Biswanath、Paidipala, Humani、Nagendra, Siddavatam

  DOI：——

  日期：——
• Synthesis, DNA-binding study, and antioxidant activity of 14-aryl-14H-dibenzo[a,j]xanthene derivatives
  作者：Andivelu Ilangovan、Karnambaram Anandhan、Kaushik Mahabir Prasad、Pakkiri Vijayakumar、Rajalingam Renganathan、Devanesan Arul Ananth、Thilagar Sivasudha

  DOI：10.1007/s00044-014-1124-8

  日期：2015.1

  A simple and efficient one-pot method for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives using Ni(ClO4)(2)center dot 6H(2)O as a catalyst is described. DNA-binding properties of 14-aryl-14H-dibenzo[a,j]xanthene derivatives 1a, 1j, 1l, 1m, and 1n were investigated using calf thymus DNA by electronic absorption spectroscopy and fluorescence spectroscopy. Binding constant (K (b)) with DNA was calculated from the absorption measurements. The spectral changes observed such as hypochromicity, red shift, and isosbestic point are consistent with the intercalation mode of binding of the chromophore into the stack DNA base pairs. Among the five, compound 1n with strong electron donating substituents on the phenyl ring shows better intercalative binding with DNA. Investigations of antioxidant properties show that the dibenzo[a,j]xanthene 1m with -OH group substitution has high radical scavenging properties against DPPH and ABTS(+).
• Magnetite–Sulfuric Acid Magnetic Nanoparticles: Preparation and Applica­tion in Synthesis of Mono-, Bis-, and Tris-14H-Dibenzo[a,j]xanthen-14-yl­arenes under Solvent-Free Conditions
  作者：Ali Karimi、Zeinab Dalirnasab、Marzie Karimi

  DOI：10.1055/s-0033-1338595

  日期：——

  Novel magnetite-sulfuric acid (Fe3O4 center dot SO3H) magnetic nanoparticles were prepared by the direct reaction of chlorosulfonic acid with magnetite nanoparticles, and characterized by IR spectroscopy, thermogravimetric analysis, X-ray diffraction, and scanning electron microscopy. The catalytic activity of the Fe3O4 center dot SO3H nanoparticles in the reaction of 2-naphthol with aryl mono-, di- and trialdehydes was examined, and these catalysts were shown to exhibit remarkable catalytic performance in the solvent-free synthesis of mono-, bis-, and tris-14H-dibenzo[a,j]xanthen-14-ylarenes. The catalyst retained its activity for several cycles.