1,3,5-三(萘-2-基)苯 | 16322-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,3,5-三(萘-2-基)苯
• 英文名称: 2-[3,5-di-(naphthalen-2-yl)-phenyl]-naphthalene
• 英文别名: 1,3,5-tri(naphthalen-2-yl)benzene；1,3,5-tris-(2'-naphthyl)benzene；1,3,5-tris(2-naphthyl)benzene；1,3,5-tri(2-naphthyl)benzene；1,3,5-tri-2-naphthylbenzene；1,3,5-tri-[2]naphthyl-benzene；2-(3,5-dinaphthalen-2-ylphenyl)naphthalene
• CAS: 16322-13-7
• 化学式: C₃₆H₂₄
• 分子量: 456.587
• InChiKey: AWIOMAWDKDFGDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-萘乙酮 在 copper dichloride 作用下， 反应 6.0h， 以33%的产率得到1,3,5-三(萘-2-基)苯
  参考文献：
  名称：

  氯化铜(II)合成三苯代苯

  摘要：

  不同的酮，如环己酮、环戊酮、苯乙酮、2-乙酰萘、4-甲基环己酮，在含水 CuCl2（催化量）的存在下，在回流条件下 2-4 小时，不使用溶剂导致二聚体 2-(1-环己烷-1-yl)-cyclohexanone 6, 2-cyclopentylidene cyclopentanone 10, trimer dodecahydrotriphenylene (DTP) 4, trindan (tricyclopentabenzo) 9, 1,3,5- triphenylbenzo (TBP) 12a, 1,3,5-tri β-naphthylbenzo 12b 和十二氢-2,6,10-三甲基苯并苯 17 和 18。

  DOI：

  10.1002/jccs.200200015

文献信息

• Nano-silica sulfuric acid catalyzed the efficient synthesis of 1,3,5-triarylbenzenes under microwave irradiation
  作者：R. Ghanbaripour、I. Mohammadpoor-Baltork、M. Moghadam、A. R. Khosropour、S. Tangestaninejad、V. Mirkhani

  DOI：10.1007/s13738-012-0089-0

  日期：2012.10

  Nano-silica sulfuric acid as a heterogeneous, eco-friendly and reusable catalyst was used in the synthesis of 1,3,5-triarylbenzenes via triple-self condensation of acetophenones. All reactions were performed under solvent-free conditions and microwave irradiation. Short reaction times, high yields, easy isolation and purification of products and good reusability of this catalyst are the mainspring to choose for the preparation of 1,3,5-triarylbenzenes.

  纳米二氧化硅硫酸作为异相、环保且可重复使用的催化剂，被用于通过乙酰苯的三重自缩合反应合成1,3,5-三芳基苯。所有反应均在无溶剂条件和微波辐射下进行。短反应时间、高产率、产品易于分离和纯化以及该催化剂的良好重复性是制备1,3,5-三芳基苯选择这种催化剂的主要原因。
• Sulfated tungstate catalyzed synthesis of C 3 -symmetric 1,3,5-triaryl benzenes under solvent-free condition
  作者：Ganesh D. Wagh、Krishnacharya G. Akamanchi

  DOI：10.1016/j.tetlet.2017.06.055

  日期：2017.8

  Sulfated tungstate catalyzed environmentally benign, simple, one pot, and solvent-free method has been developed for the synthesis of 1,3,5-triarylbenzenes via cyclic self-condensation of three molecules of aryl ketones. High yields, short reaction time, easy work-up procedure and recycling of the catalyst endorse advantage.

  已开发出硫酸钨酸盐催化的环境友好，简单，一锅又无溶剂的方法，用于通过三个分子的芳基酮的循环自缩合反应来合成1,3,5-三芳基苯。产率高，反应时间短，后处理容易和催化剂的循环利用具有优势。
• Triple condensation of aryl methyl ketones catalyzed by amine and trifluoroacetic acid: straightforward access to 1,3,5-triarylbenzenes under mild conditions
  作者：Shao-Liang Zhang、Zhao-Feng Xue、Ya-Ru Gao、Shuai Mao、Yong-Qiang Wang

  DOI：10.1016/j.tetlet.2012.03.008

  日期：2012.5

  An efficient triple condensation reaction of aryl methyl ketones catalyzed by ethylenediamine and trifluoroacetic acid was reported. A broad scope of 1,3,5-triarylbenzenes was obtained in good to excellent yields. The reaction provides a novel and practical approach to access organic materials of polycyclic aromatic hydrocarbons under mild conditions.

  报道了乙二胺和三氟乙酸催化的芳基甲基酮的有效三重缩合反应。以良好至优异的产率获得了广泛的1,3,5-三芳基苯。该反应为在温和条件下接触多环芳烃的有机材料提供了一种新颖而实用的方法。
• Triple Self-Condensation of Ketones Yielding Aromatics Promoted with Titanium Tetrachloride
  作者：Zilong Li、Wen-Hua Sun、Xianglin Jin、Changxing Shao

  DOI：10.1055/s-2001-18771

  日期：——

  Triple self-condensation of ketones was promoted by titanium tetrachloride in toluene to afford corresponding benzene derivatives, and the structure of tri(2-naphthyl)benzene was confirmed by X-ray single crystal diffraction.

  三重自缩合反应在四氯化钛的促进下于甲苯中进行，产生产物苯衍生物，并通过X射线单晶衍射证实了三(2-萘基)苯的结构。
• Highly selective biaryl formation by the cyclooligomerization of arylethynes catalyzed by rhodium and ruthenium porphyrins
  作者：Pietro Tagliatesta、Elfituri Elakkari、Alessandro Leoni、Angelo Lembo、Daniel Cicero

  DOI：10.1039/b806025h

  日期：——

  Rhodium and ruthenium porphyrins catalyze the one-pot formation of biaryl derivatives from arylethynes with high selectivity, giving interesting derivatives not easy to obtain using other different methods; the porphyrin catalysts can be recovered and reused after several experiments with no change of activity.

  铑和钌卟啉催化剂选择性高地实现了从芳烃乙炔一锅法合成二芳基衍生物，得到的有趣衍生物不易通过其他方法获得；卟啉催化剂在多次实验后可以回收并重复使用，活性没有变化。