anthracene-1,4-dicarbaldehyde | 197856-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: anthracene-1,4-dicarbaldehyde
• 英文别名: anthracene-1,4-dicarboxaldehyde
• CAS: 197856-66-9
• 化学式: C₁₆H₁₀O₂
• 分子量: 234.254
• InChiKey: ZVEIMOAZWKSSKF-UHFFFAOYSA-N

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

反应信息

• 作为反应物：
  描述：

  4,5-二氰咪唑-2-肼溴化氢 、 anthracene-1,4-dicarbaldehyde 以 乙醇 为溶剂， 反应 5.0h， 以44%的产率得到anthracene-1,4-dicarboxaldehyde bis[(4,5-dihydro-1H-imidazol-2-yl)hydrazone] dihydrobromide
  参考文献：
  名称：

  1,4-Disubstituted Anthracene Antitumor Agents

  摘要：

  Three different types of 1,4-disubstituted anthracenes were synthesized, and their cytotoxicity in a panel of tumor cells was compared with that of the corresponding 9,10-disubstituted anthracenes. The panel contained human myeloma, melanoma, colon, and lung cancer cells and sensitive and multidrug-resistant murine L1210 leukemia cells. These compounds had [[(dimethylamino>ethyl]amino]methyl, N-[(dimethylamino)ethyl]carbamoyl, and carboxaldehyde (4,5-dihydro-1H-imidazol-2-yl)hydrazone side chains. The 1,4-diamide was more potent across the tumor panel than the corresponding 9,10-isomer, but the 1,4-diamine and the 1,4-hydrazone were less potent than their 9,10-isomers. Although the 1,Li-hydrazone was active against P388 leukemia in mice, it was inactive against L1210 leukemia. Within each pair of compounds, the one with greater average potency against tumor cells gave a greater increase in the transition melt temperature of DNA.

  DOI：

  10.1021/jm970308+
• 作为产物：
  描述：

  1,4-蒽二甲酸 在 吗啉 、 potassium carbonate 、 红铝 作用下， 以 甲苯 、 丁酮 为溶剂， 生成 anthracene-1,4-dicarbaldehyde
  参考文献：
  名称：

  Synthesis, DNA-damaging and cytotoxic properties of novel topoisomerase II-directed bisantrene analogues

  摘要：

  New bisantrene analogues were synthesized, bearing one or two 4,5-dihydro-1H-imidazol-2-yl hydrazone side chains at positions 1,4 or 9 of the anthracene ring system. A 10-aza-bioisostere was also prepared. The position of substituents in structurally isomeric drugs modulates topoisomerase II poisoning and specificity, along with cytotoxicity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(97)10207-4

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。
• Twofold π-Extension of Polyarenes via Double and Triple Radical Alkyne <i>peri</i>-Annulations: Radical Cascades Converging on the Same Aromatic Core
  作者：Edgar Gonzalez-Rodriguez、Miguel A. Abdo、Gabriel dos Passos Gomes、Suliman Ayad、Frankie D. White、Nikolay P. Tsvetkov、Kenneth Hanson、Igor V. Alabugin

  DOI：10.1021/jacs.0c01856

  日期：2020.5.6

  Sn-radical attack at the triple bonds. The two peri-annulations converge at a variety of polycyclic cores to yield expanded difunctionalized polycyclic aromatic hydrocarbons (PAHs). This approach can be extended to triple peri-annulations, where annulations are coupled with a radical cascade that connects two preexisting aromatic cores via a formal C-H activation step. The installed Bu3Sn groups serve as chemical

  通过双自由基周围环化开发了一种合成二甲烷基取代的聚芳烃的通用途径。环化前体配备有炔丙基 OMe 无痕导向基团 (TDG)，用于区域选择性 Sn 自由基攻击三键。两个环环会聚在各种多环核上，以产生膨胀的双官能化多环芳烃 (PAH)。这种方法可以扩展到三重环化，其中环化与自由基级联耦合，通过正式的 CH 活化步骤连接两个预先存在的芳香核。安装的 Bu3Sn 基团作为化学处理，通过直接交叉偶联、碘化或原脱甲基化进一步功能化，并增加产品在有机溶剂中的溶解度。光物理研究表明，Bu3Sn 取代的多环芳烃具有中等荧光，它们的原去甲酰化导致荧光量子产率提高了 10 倍。DFT 计算确定了这种复杂化学转化最可能的机制，涉及中心核心的两个独立的周环化。
• COMPOUNDS HAVING ELECTROLUMINESCENT OR ELECTRON TRANSPORT PROPERTIES
  申请人：Kathirgamanathan Poopathy

  公开号：US20110006295A1

  公开（公告）日：2011-01-13

  A compound of the formula R 1 (CR 3 ═CR 4 )nAr(CR 4 ═CR 3 ) n R 2 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 with alkoxy, fluoro, fluoroalkyl or cyano and which in the case of a 5-membered ring nitrogen heteroatom may be N-substituted with aryl or substituted aryl optionally further substituted with alkoxy, fluoro, fluoroalkyl or cyano; R 1 and R 2 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 with alkoxy, fluoro, fluoroalkyl or cyano; and R 3 and R 4 independently represent hydrogen, methyl, ethyl or benzyl. Also provided 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 or may be further substituted by aryl or heteroaryl having from one to four aromatic rings, said aryl or heteroaryl substituent or substituents optionally being substituted with one or more fluoro, fluoroalkyl or cyano substituents. The condensation may be carried out in acetic anhydride under reflux. The compounds may be incorporated e.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. A composition is provided comprising a compound as above and a second host or electron transport material and/or at least one dopant.

  该化合物的化学式为R1(CR3═CR4)nAr(CR4═CR3)nR2，其中：n为0或1；Ar代表芳香族或杂环芳香族，具有1-5个芳香环，可以是链式的、融合的或链式和融合的组合，可以用烷氧基、氟、氟烷基或氰基取代，在5-成员环氮杂原子的情况下，可以用芳基或取代芳基N-取代，可选择进一步用烷氧基、氟、氟烷基或氰基取代；R1和R2独立地代表芳基或含有两个到四个融合芳香环的氮、氧或硫杂环，其中一个可能是5-成员环，并可选择用具有1-5个链式或融合芳香环的芳基或杂环芳基进一步取代，这些芳基或杂环芳基可能进一步用烷氧基、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。还提供了一种具有电致发光和/或电导性能的化合物的制备方法，该方法包括将芳香二醛与具有两到四个融合环的甲基取代杂环化合物缩合，该杂环化合物可以是未取代的或进一步由具有1到4个芳香环的芳基或杂环芳基取代，该芳基或杂环芳基取代基可选择进一步用一个或多个氟、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，例如被纳入到光学发光二极管中，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，或被纳入到静电成像成员中。还提供了一种组合物，包括上述化合物和第二宿主或电子传输材料和/或至少一种掺杂剂。
• PROCESS FOR PRODUCING M-XYLYLENEDIAMINE
  申请人：RHODIA OPERATIONS

  公开号：EP3674285A1

  公开（公告）日：2020-07-01

  A process for the production of m-xylylenediamine, by reacting isophthalaldehyde with hydrogen and ammonia or an ammonia-liberating compound, in the presence of a hydrogenation catalyst and an amine, wherein the molar ratio of the amine to isophthalaldehyde is no less than 1:4 at the start of the reaction.

  一种间苯二胺的生产工艺，在氢化催化剂和胺的存在下，间苯二甲醛与氢气和氨或氨释放化合物反应，其中胺与间苯二甲醛的摩尔比在反应开始时不小于 1:4。
• Process for producing aromatic primary diamines
  申请人：RHODIA OPERATIONS

  公开号：US10899726B2

  公开（公告）日：2021-01-26

  A process for the production of aromatic primary amines, by reacting an aromatic dialdehyde with hydrogen and ammonia or an ammonia-liberating compound, in the presence of a hydrogenation catalyst and an amine, wherein the molar ratio of the amine to the aromatic dialdehyde is no less than 1:4 at the start of the reaction.

  一种芳香族伯胺的生产工艺，在氢化催化剂和胺的存在下，使芳香族二醛与氢气和氨或氨释放化合物反应，其中胺与芳香族二醛的摩尔比在反应开始时不小于 1:4。