14-(2-methylphenyl)-14H-dibenzo[a,j]xanthene | 66596-02-9

• 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: 14-(2-methylphenyl)-14H-dibenzo[a,j]xanthene
• 英文别名: 14-(2-methyl)14-H-dibenzo[a,j]xanthene；2-(2-methylphenyl)-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: 66596-02-9
• 化学式: C₂₈H₂₀O
• 分子量: 372.466
• InChiKey: OZGXWUXVLGDJOB-UHFFFAOYSA-N

物化性质

• 熔点：
  208 °C(Solv: acetic acid (64-19-7))
• 沸点：
  541.7±45.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.59
• 重原子数：
  29.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-甲基苯甲醛 、 2-萘酚 在 C₁₄H₃₄N₂O₆S₂⁽²⁺⁾*2HO₄S^(1-) 作用下， 以 neat (no solvent) 为溶剂， 以70%的产率得到14-(2-methylphenyl)-14H-dibenzo[a,j]xanthene
  参考文献：
  名称：

  特定任务的双阳离子酸性离子液体催化高效，快速合成苯并黄酮酮衍生物

  摘要：

  已经开发出一种快速而直接的方法，该方法使用任务特定的阳离子酸性离子液体作为无溶剂条件下的高效且易于获得的催化剂，来合成二苯并[a，j]黄嘌呤和1,8-二氧代-八氢黄酮。制备了一系列的Brønsted-Lewis酸性离子液体，并研究了它们对从醛和2-萘酚或二甲酮合成各种黄酮衍生物的催化活性。无需有机溶剂和柱色谱法即可轻松进行产物分离，以及酸性离子液体催化剂的可重复使用性，使得该方法对于大规模合成而言经济实惠。

  DOI：

  10.1016/j.molliq.2016.07.128

文献信息

• Microwave-assisted green synthesis of dibenzo[a,j]xanthenes using p-dodecylbenzenesulfonic acid as an efficient Bronsted acid catalyst under solvent-free conditions
  作者：Davinder Prasad、Amreeta Preetam、Mahendra Nath

  DOI：10.1016/j.crci.2012.05.018

  日期：2012.8

  Résumé The p-dodecylbenzenesulfonic acid (DBSA) has been successfully applied as an efficient acidic catalyst for the microwave-assisted synthesis of a series of 14-aryl- or alkyl-14H-dibenzo[a,j]xanthenes (3a-m) via a one-pot condensation-cyclization reaction of β-naphthol with various aliphatic or aromatic aldehydes under solvent-free conditions. Operational simplicity, short reaction times, excellent yields and environmentally-benign conditions are other advantages of this protocol. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.doc

  摘要：十二烷基苯磺酸（DBSA）已成功应用于微波辅助合成一系列14-芳基或烷基-14H-二苯并[a,j]吖啶（3a-m），通过β-萘酚与各种脂肪族或芳香族醛在无溶剂条件下的一锅缩合-环化反应。操作简便、反应时间短、产率高以及环境友好条件是该方法的其他优点。 补充材料：本文的补充材料以单独文件形式提供：mmc1.doc
• Efficient one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives promoted by niobium pentachloride
  作者：Aloisio Andrade Bartolomeu、Manoel Menezes、Luiz Silva Filho

  DOI：10.2478/s11696-014-0597-8

  日期：2014.1.1

  A simple and efficient procedure for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives through one-pot condensation of 2-naphthol with aryl aldehydes in the presence of niobium pentachloride is described. The reactions were carried out using 25 mole % of NbCl5, at ambient temperature, and in acceptable reaction times, affording excellent yields of the products.

  本文描述了一种简单高效的方法，通过在铌五氯化物存在下，将2-萘酚与芳基醛一锅法缩合合成14-芳基-14H-二苯并[a,j]黄芩烷衍生物。反应在常温下使用25摩尔%的NbCl5进行，反应时间合适，产率优异。

• Fe2+ supported on hydroxyapatite-core–shell-γ-Fe2O3 nanoparticles: Efficient and recyclable green catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives
  作者：Hakimeh Sadat Haeri、Sobhan Rezayati、Eshagh Rezaee Nezhad、Hamed Darvishi

  DOI：10.1007/s11164-015-2318-5

  日期：2016.5

  electron microscopy, and vibrating sample magnetometry spectra. Then, γ -Fe2O3–HAp-Fe2+ NPs were used as an efficient, reusable and heterogeneous nanocatalyst for one-pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes via the one-pot condensation reaction of arylaldehydes and 2-naphthol under solvent-free conditions in good to excellent yields. This procedure has a lot of advantages such as very easy

  在这项工作中，铁2+支撑在羟基磷灰石的核-壳- γ -Fe 2 ö 3纳米颗粒（ γ -Fe 2 ö 3 -HAp -铁2+的NP）已被制备和表征通过傅里叶变换红外光谱，X-射线衍射，透射电子显微镜，扫描电子显微镜和振动样品磁强光谱。然后， γ -Fe 2 O 3 -HAp-Fe 2+通过无溶剂条件下芳基醛和2-萘酚的一锅缩合反应，NPs被用作一种高效，可重复使用的多相纳米催化剂，用于一锅合成14-芳基-14H-二苯并[a，j]黄嘌呤。高产。该方法具有许多优点，例如非常容易的反应条件，操作简单，反应时间短，产率高以及通过避免有毒的常规催化剂和溶剂而具有绿色方面。此外， γ -Fe 2 O 3 -HAp-Fe 2+ NPs易于从反应混合物中回收，可以重复使用七次而不会损失活性。
• Design, fabrication and characterization of magnetic nickel copper ferrite nanocomposites and their application as a reusable nanocatalyst for sonochemical synthesis of 14-aryl-14-H-dibenzo[a,j]xanthene derivatives
  作者：Azin Alipour、Hossein Naeimi

  DOI：10.1007/s11164-023-04981-0

  日期：——

  In this research, 14-aryl-14-H-dibenzo[a,j]xanthene derivatives have successfully prepared through one pot reaction of the aldehyde derivatives and 2-naphthol employing the as-fabricated NiCuFe2O4 magnetic nanocatalyst under ultrasound irradiation. The structure of achieved derivatives was identified by using FT-IR, 1H NMR and melting point analyses. Moreover, FT-IR, XRD, FE-SEM, EDX, and VSM techniques

  在这项研究中，14-aryl-14-H-dibenzo[a,j]xanthene derivatives have successfully by a pot reaction of the aldehyde derivatives and 2-naphthol using the as-fabricated NiCuFe 2 O 4 magnetic nanocatalyst under ultrasound radiation . 通过使用 FT-IR、 1 H NMR 和熔点分析确定了所获得衍生物的结构。此外，应用 FT-IR、XRD、FE-SEM、EDX 和 VSM 技术来验证 NiCuFe 2 O 4的结构磁性纳米粒子。该协议涉及值得注意的方面，例如；使用外部磁体的催化剂易于处理、节省成本、优异的产率和可重复使用性。此外，用过的纳米催化剂在五次运行中被回收再利用，其催化活性略有下降。
• Magnesium Hydrogensulfate [Mg(HSO₄)₂] as an Efficient Catalyst for the Preparation of Silyl Ethers, Dibenzo[a,j]xanthenes, and Octahydroxanthene Derivatives
  作者：Hamid Reza Shaterian、Razieh Doostmohammadi、Fahimeh Khorami、Majid Ghashang

  DOI：10.1080/10426500902758329

  日期：2009.12.29

  Magnesium hydrogensulfate [Mg(HSO4)(2)], as a heterogeneous solid acid catalyst, has been used for the mild formation of trimethylsilyl (TMS) ethers from various primary, secondary, and tertiary aliphatic alcohols; aromatic alcohols; and oximes using hexamethyldisilazane (HMDS) under ambient conditions. In addition, 14-aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo- octahydroxanthene derivatives were synthesized in the presence of Mg(HSO4)(2) with short reaction times in high to excellent yield under solvent-free conditions.