四乙基萘-1,2,3,4-四羧酸酯 | 107002-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 四乙基萘-1,2,3,4-四羧酸酯
• 英文名称: tetraethyl naphthalene-1,2,3,4-tetracarboxylate
• 英文别名: tetraethyl naphtalene-1,2,3,4-tetracarboxylate
• CAS: 107002-74-4
• 化学式: C₂₂H₂₄O₈
• 分子量: 416.428
• InChiKey: BDRZKOBUAXOEON-UHFFFAOYSA-N

物化性质

• 熔点：
  94-96 °C
• 沸点：
  478.7±40.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,2-二碘苯 、 丁炔二酸二乙酯 在 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 、 1,2-双(二苯基膦)乙烷 、 锌 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以75%的产率得到四乙基萘-1,2,3,4-四羧酸酯
  参考文献：
  名称：

  邻二卤代芳烃作为炔烃前体，用于炔烃和腈与镍催化的[2 + 2 + 2]环加成反应。

  摘要：

  用作芳烃前体的邻二卤代芳烃与乙炔和NiBr（2）（dppe）/ dppe / Zn系统催化的腈反应，根据反应条件，以中等到极好的收率得到取代的萘，菲啶或联苯衍生物，具有良好的耐受性功能组。

  DOI：

  10.1039/b801870g

文献信息

• Rhodaelectrocatalysis for Annulative C−H Activation: Polycyclic Aromatic Hydrocarbons through Versatile Double Electrocatalysis
  作者：Wei‐Jun Kong、Lars H. Finger、João C. A. Oliveira、Lutz Ackermann

  DOI：10.1002/anie.201901565

  日期：2019.5.6

  Rapid access to structurally diversified polycyclic aromatic hydrocarbons (PAHs) in a controlled manner is of key significance in materials sciences. Herein, we describe a strategy featuring two distinct electrocatalytic C−H transformations for the synthesis of novel nonplanar PAHs. The combination of rhodaelectrooxidative C−H activation/[2+2+2] alkyne annulation of easily accessible boronic acids with

  在材料科学中，以受控方式快速获得结构多样的多环芳烃（PAH）至关重要。在这里，我们描述了一种以两种不同的电催化CH转化为特征的策略，用于合成新型非平面PAH。易于获得的硼酸的rhodaelectrooxidative CH-H活化/ [2 + 2 + 2]炔烃环化与电催化环脱氢的组合，提供了模块化的途径，可替代地将PAHs与电作为可持续的氧化剂。全面分析了由此获得的多环芳烃的独特分子拓扑结构以及光物理和电子性质。这种金属电化学催化方法的独特功能通过合成有用的碘取代的PAH的化学选择性组装得到了证明。
• Synthesis of Highly Substituted Acenes through Rhodium-Catalyzed Oxidative Coupling of Arylboron Reagents with Alkynes
  作者：Tatsuya Fukutani、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/jo200339w

  日期：2011.4.15

  The rhodium-catalyzed oxidative 1:2 coupling reactions of arylboronic acids or their esters with alkynes smoothly proceed to produce the corresponding annulated products. Of special note, highly substituted, readily soluble, and tractable anthracene and tetracene derivatives can be obtained selectively from 2-naphthyl- and 2-anthrylboron reagents, respectively.

  芳基硼酸或其酯与炔烃的铑催化的氧化1：2偶联反应平稳进行，得到了相应的环状产物。特别值得注意的是，可以分别从2-萘基和2-蒽硼试剂中选择性地获得高度取代，易溶且易于处理的蒽和并四苯衍生物。
• PALLADIUM-PROMOTED AROMATIC ANNELATION WITH ACETYLENE DICARBOXYLATES
  作者：Tsutomu Sakakibara、Yasuo Tanaka、Shin-ichi Yamasaki

  DOI：10.1246/cl.1986.797

  日期：1986.5.5

  Benzene rings of N-alkyltoluidine and benzene (or iodobenzene) in acetic acid were annelated with acetylenedicarboxylates by palladium(II) acetate to give N-alkylindole-2,3-dicarboxylate and naphthalene-1,2,3,4-tetracarboxylate. The formation of the products are explained in terms of toluidine radical cation intermediates.

  乙酸中的 N-烷基甲苯胺和苯（或碘苯）的苯环在乙酸钯（II）的作用下与乙炔二羧酸盐发生羰基化反应，生成 N-烷基吲哚-2,3-二羧酸盐和萘-1,2,3,4-四羧酸盐。这些产物的形成可以用甲苯胺自由基阳离子中间体来解释。
• Synthesis of Tetrasubstituted Naphthalenes by Palladium-Catalyzed Reaction of Aryl Iodides with Internal Alkynes
  作者：Satoshi Kawasaki、Tetsuya Satoh、Masahiro Miura、Masakatsu Nomura

  DOI：10.1021/jo0346656

  日期：2003.8.1

  acetylenedicarboxylate esters and diphenylacetylene efficiently proceeds in the presence of a palladium catalyst with use of silver carbonate as base to produce the corresponding tetrasubstituted naphthalenes.

  在钯催化剂存在下，以碳酸银为碱，芳基碘化物与乙炔二羧酸酯和二苯乙炔的1：2偶联有效地进行，以产生相应的四取代萘。
• Rhodium-Catalyzed Desulfination of Sodium Arenesulfinates and Oxidative Annulation with Alkynes
  作者：Hui Wang、Yuyuan Wang、Haijun Yang、Chunyan Tan、Yuyang Jiang、Yufen Zhao、Hua Fu

  DOI：10.1002/adsc.201400930

  日期：2015.2.9

  AbstractPolycyclic aromatic compounds are widely used in materials science, so it is highly desirable to develop an efficient and practical approach to them. In this paper, a novel, efficient and practical method for the rhodium(III)‐catalyzed desulfination of sodium arenesulfinates and oxidative annulation with alkynes has been developed, and the corresponding polycyclic aromatic compounds with multiple substituents were prepared in moderate to good yields. The reactions proceeded through sequential rhodium(III)‐catalyzed desulfination, intermolecular addition of aryl‐Rh(III) complexes to dialkyl but‐2‐ynedioates and diarylalkynes, and intramolecular oxidative annulation via CH activation. The present method is the first example of the oxidative annulation of arene derivatives with two different alkynes. Therefore, it should afford a useful strategy for the synthesis of polycyclic aromatic compounds.magnified image