蒽-2,3-二羧醛 | 76197-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 蒽-2,3-二羧醛
• 中文别名: 2,3-蒽二甲醛
• 英文名称: anthracene-2,3-dicarbaldehyde
• 英文别名: 2,3-Anthracenedicarboxaldehyde
• CAS: 76197-35-8
• 化学式: C₁₆H₁₀O₂
• 分子量: 234.254
• InChiKey: HTKKRNQMBYGFMV-UHFFFAOYSA-N

物化性质

• 熔点：
  220 °C (sublm)(Press: 0.1 Torr)
• 沸点：
  477.1±28.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2912299000

反应信息

• 作为反应物：
  描述：

  蒽-2,3-二羧醛 在 肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以79%的产率得到Naphtho<2,3-g>phthalazine
  参考文献：
  名称：

  Convenient Syntheses of Naphthalene-, Anthracene-, and Naphthacene-2,3-dicarboxaldehydes

  摘要：

  DOI：

  10.1055/s-1980-29170
• 作为产物：
  描述：

  2,3-萘基二缩醛 在 lithium aluminium tetrahydride 、 溶剂黄146 、 三苯基膦 作用下， 生成 蒽-2,3-二羧醛
  参考文献：
  名称：

  Phosphine-Mediated Iterative Arene Homologation Using Allenes

  摘要：

  A PPh3-mediated multicomponent reaction between o-phthalaldehydes, nucleophiles, and monosubstituted allenes furnishes functionalized non-C-2-symmetric naphthalenes in synthetically useful yields. When the o-phthalaldehydes were reacted with 1,3-disubstituted allenes in the presence of PPh2Et, naphthalene derivatives were also obtained in up to quantitative yields. The mechanism of the latter transformation is straightforward: aldol addition followed by Wittig olefination and dehydration. The mechanism of the former is a tandem gamma-umpolung/aldol/Wittig/dehydration process, as established by preparation of putative reaction intermediates and mass spectrometric analysis. This transformation can be applied iteratively to prepare anthracenes and tetracenes using carboxylic acids as pronucleophiles.

  DOI：

  10.1021/jacs.5b07403

文献信息

• [EN] COMPOUNDS HAVING ELECTROLUMINESCENT OR ELECTRON TRANSPORT PROPERTIES<br/>[FR] COMPOSÉS PRÉSENTANT DES PROPRIÉTÉS ÉLECTROLUMINESCENTES OU DE TRANSPORT DES ÉLECTRONS
  申请人：MERCK PATENT GMBH

  公开号：WO2009112854A1

  公开（公告）日：2009-09-17

  A compound of the formula R1 (CR3 =CR4 ) nAr(CR4 =CR3 ) nR2 wherein: n is 0 or 1; Ar represents aryl or heteroaryl having 1-5 aromatic rings which may be chain or fused or a combination of chain and fused, which may be substituted withalkoxy, fluoro, fluoroalkyl or cyano and which in the case of a 5-memnered ring nitrogen heteroatom may be N-substituted with aryl or substituted aryl optionally further substituted with alkoxy, fluoro, fluoroalkyl or cyano; R1 and R2 independently represent aryl or nitrogen, oxygen or sulphur-containing heteroaryl having two to four fused aromatic rings one of which may be 5-membered and optionally substituted by aryl or heteroaryl having 1-5 chain or fused aromatic rings which may be further substituted withalkoxy, fluoro, fluoroalkyl or cyano; and R3 and R4 independently represent hydrogen, methyl, ethyl or benzyl. Alsoprovided is a method of making a compound having electroluminescent and/or electroconductive properties, which comprises condensing an aromatic dialdehyde with a methyl-substituted heteroaryl compound having two to four fused rings which maybe unsubstituted ormay be further substituted by aryl or heteroaryl having from one to fouraromatic rings, said aryl or heteroaryl substituent or substituents optionally being substituted with one or more fluoro, fluoroalkyl orcyano substituents.The condensation may be carried out in acetic anhydride under reflux. The compounds may be incorporatede.g. as an electron transport layer into an optical light emitting diode,where embodiments can provide high electron mobility, low turn-on voltage and good lifetime,or into an electrostatic imaging member. Acompositionis provided comprising a compound as above and a second host or electron transport material and/or at leastone dopant.

  一个化合物的结构式为R1（CR3=CR4）nAr（CR4=CR3）nR2，其中：n为0或1；Ar代表含有1-5个芳香环的芳基或杂芳基，可以是链状的、融合的或链状和融合的组合，可以被烷氧基、氟、氟烷基或氰基取代，在5-成员环氮杂原子的情况下，可能被芳基或取代芳基N-取代，可选择地进一步取代为烷氧基、氟、氟烷基或氰基；R1和R2独立地代表含有两到四个融合芳香环的芳基或氮、氧或硫杂杂芳基，其中一个可能是5-成员的，并且可选择地被芳基或含有1-5个链状或融合芳香环的杂芳基取代，这些芳基或杂芳基可能进一步被烷氧基、氟、氟烷基或氰基取代；R3和R4独立地代表氢、甲基、乙基或苄基。还提供了一种制备具有电致发光和/或电导性能的化合物的方法，包括将芳香二醛与一种具有两到四个融合环的甲基取代的杂芳基化合物缩合，该化合物可能未取代或可能进一步被含有一到四个芳香环的芳基或杂芳基取代，所述芳基或杂芳基取代物可选择地被一个或多个氟、氟烷基或氰基取代。缩合可以在乙酸酐中回流进行。这些化合物可以被用作电子传输层，例如用于光电发光二极管，其中实施例可以提供高电子迁移率、低开启电压和良好的寿命，或用于静电成像成员。提供了一种组合物，包括上述化合物和第二宿主或电子传输材料和/或至少一个掺杂剂。
• Iterative synthesis of acenesvia homo-elongation
  作者：Chih-Hsiu Lin、Ke-Han Lin、Bikash Pal、Li-Der Tsou

  DOI：10.1039/b814840f

  日期：——

  Starting from aromaticortho-dialdehydes, we devised a homo-elongation protocol that combines a Wittig olefination and subsequent intramolecular Knoevenagel condensation to produce acene diesters and dinitriles.

  从芳香邻二醛出发，我们设计了一套同系延长方案，结合了Wittig烯化反应和随后的分子内Knoevenagel缩合反应，以生成并五烷二酯和二腈。
• NHC‐Catalyzed Desymmetrization of N‐Aryl Maleimides Leading to the Atroposelective Synthesis of N‐Aryl Succinimides
  作者：Soumen Barik、Sayan Shee、Soumik Das、Rajesh G. Gonnade、Garima Jindal、Subrata Mukherjee、Akkattu T. Biju

  DOI：10.1002/anie.202016938

  日期：2021.5.25

  leading to the atroposelective synthesis of biaryls and allied compounds are well‐known, the related synthesis of compounds bearing axially chiral C−N bonds are relatively rare. Described herein is the N‐heterocyclic carbene‐catalyzed atroposelective synthesis of N‐aryl succinimides having an axially chiral C−N bond via the desymmetrization of N‐aryl maleimides. The NHC involved intermolecular Stetter‐aldol

  尽管导致手性C-C键的轴向合成导致联芳基和相关化合物的对映选择性合成是众所周知的，但带有轴向手性C-N键的化合物的相关合成却相对较少。本文描述的是通过N-芳基马来酰亚胺的去对称化作用，对具有轴向手性C-N键的N-芳基琥珀酰亚胺进行N-杂环卡宾催化的对位选择性合成。NHC涉及分子间的二醛与前手性N-芳基马来酰亚胺的分子间Stetter-aldol级联反应，然后氧化得到N-芳基琥珀酰亚胺，具有良好的收率和ee值。还提供了有关C–N键的旋转势垒，温度依赖性的初步研究，以及有关机理的详细DFT研究。
• Base-Catalyzed One-Pot Synthesis of Unsymmetrical Fluorenes from Aromatic <i>ortho</i> -Dialdehydes and 1,3-Dicarbonyl Compounds
  作者：Ue Ryung Seo、Young Keun Chung、Chulbom Lee

  DOI：10.1002/cctc.201501424

  日期：2016.3.18

  A synthetic route for the preparation of unsymmetrically polysubstituted fluorenes was developed through the base‐catalyzed one‐pot domino reactions of aromatic ortho‐dialdehydes with 1,3‐dicarbonyl compounds. This protocol provides expeditious access to indene‐fused polycyclic aromatic hydrocarbons such as the benzo[b]fluorene and 13H‐indeno[1,2‐b]anthracene skeletons.

  通过芳族邻二醛与1,3-二羰基化合物的碱催化单锅多米诺反应，开发了一种制备不对称多取代芴的合成途径。该协议可快速访问茚并稠合的多环芳烃，例如苯并[ b ]芴和13 H-茚并[1,2-b]蒽骨架。
• Aromatic methylidene compound, methylstyryl compound for producing the same, production method therefor, and organic electroluminescent element
  申请人：Hashimoto Mitsuru

  公开号：US20050096491A1

  公开（公告）日：2005-05-05

  A compound of the formula (1): wherein R 11 represents an alkyl group, an alkoxy group, a halogen atom, a cyano group, or a nitro group; n 11 is an integer of 0 to 4; R 21 and R 31 are a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic group, or a heteroaromatic group; or R 21 and R 31 together form a condensed ring consisting of aromatic rings or heteroaromatic rings; and Ar is selected from the groups consisting of groups represented by the following formulae: and a methylstyryl compound for producing the same, the production methods thereof and an organic electroluminescent element having the compound.

  该化合物的化学式为(1)：其中R11代表烷基基团、烷氧基团、卤素原子、氰基或硝基基团；n11是0到4的整数；R21和R31分别是氢原子、烷基基团、环烷基基团、芳香基团或杂芳基团；或者R21和R31一起形成由芳香环或杂芳环组成的缩合环；Ar选择自下列化合物组成的基团：以及用于产生该化合物的甲基苯乙烯化合物，其生产方法和具有该化合物的有机电致发光元件。