2,3,5,6-tetrakis(4-methoxyphenyl)pyrazine | 21885-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,3,5,6-tetrakis(4-methoxyphenyl)pyrazine
• CAS: 21885-49-4
• 化学式: C₃₂H₂₈N₂O₄
• 分子量: 504.585
• InChiKey: KVZVGOZRMLAIDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetrakis(4-methoxyphenyl)pyrazine 在 三氟二甲基硫醚络合物 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到4,4′,4″,4‴-(pyrazine-2,3,5,6-tetrayl)tetraphenol
  参考文献：
  名称：

  Estrogenic diazenes: heterocyclic non-steroidal estrogens of unusual structure with selectivity for estrogen receptor subtypes

  摘要：

  Estrogens regulate many biological functions, often acting in a tissue-selective manner. Their tissue-selective action is believed to involve differential estrogen action through the two estrogen receptor (ER) subtypes, ERalpha and ERbeta, as well as differential interaction of the ligand-receptor complexes with promoters and coregulator proteins. In the latter case, selectivity is based on the induction of specific conformations of the ligand-ER complex, conformations that are influenced by the structure of the ligand. Estrogen pharmaceuticals having an ideal balance of tissue-selective activity are being sought for menopausal hormone replacement, breast cancer prevention and therapy, and other actions. To expand on the structural diversity of ER ligands that might show such tissue selectivity, we have prepared a series of diazenes (pyrazines, pyrimidines, and pyridazines) substituted with two to four aryl groups and various short-chain aliphatic substituents. All of the pyrazine and pyrimidines bind to ER, some with high affinity and with a considerable degree of preferential binding to either ERalpha or ERbeta. One pyrimidine and one pyrazine have ERalpha affinity preferences as high as 23 and 9, respectively, and one pyrimidine has an ERP affinity preference of 8. The pyridazines, by contrast, are quite polar and have only very low binding affinity for the ER. In cell-based transcription assays, several of the pyrimidines and a pyrazine were found to be considerably more agonistic on ERalpha than on ERbeta. Because these triaryl diazenes have the largest volumes among the ER ligands so far investigated, their high affinity demonstrates the flexibility of the ligand binding pocket of the ERs and its tolerance for large substituents. Thus, these novel heterocyclic ligands expand the repertoire of chemical structures that bind to the estrogen receptor, and they could prove to be useful in elucidating the biological behavior of the two ER subtypes and in forming the basis for new estrogen pharmaceuticals having desirable tissue selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00309-7
• 作为产物：
  描述：

  1-amino-1-(p-methoxyphenyl)-4'-methoxyacetophenone 以 乙醇 为溶剂， 反应 2.0h， 生成 2,3,5,6-tetrakis(4-methoxyphenyl)pyrazine
  参考文献：
  名称：

  Photochemistry of vinyl halides. Heterocycles from reaction of photogenerated vinyl cations with azide anion

  摘要：

  DOI：

  10.1021/jo00199a003

文献信息

• An Improved Synthesis of Multi-Substituted Pyrazines under Catalyst- and Solvent-Free Conditions
  作者：Fatemeh Tamaddon、Arefeh Tafti、Farzaneh Pooramini

  DOI：10.1055/s-0035-1562789

  日期：——

  and solvent-free conditions. This procedure provides a synthetic method to access pyrazine derivatives in excellent yields under green conditions. A one-pot pseudo four-component reaction between a variety of 2-hydroxy-1,2-diarylethanone derivatives and ammonium acetate or amines has been developed to synthesize substituted pyrazines under catalyst-free and solvent-free conditions. This procedure provides

  摘要 已经开发出了各种2-羟基-1，2-二芳基酮衍生物与乙酸铵或胺之间的一锅法假四组分反应，可以在无催化剂和无溶剂条件下合成取代的吡嗪。该方法提供了一种在绿色条件下以优异的产率获得吡嗪衍生物的合成方法。 已经开发出了各种2-羟基-1，2-二芳基酮衍生物与乙酸铵或胺之间的一锅法假四组分反应，可以在无催化剂和无溶剂条件下合成取代的吡嗪。该方法提供了一种在绿色条件下以优异的产率获得吡嗪衍生物的合成方法。
• SnCl2·2H2O-Catalyzed Solvent-Free Synthesis of α-Amino Ketones and Tetrasubstituted Pyrazines
  作者：Fatemeh Tamaddon、Arefeh Dehghani Tafti

  DOI：10.1055/s-0035-1561663

  日期：——

  α-amino ketones in excellent yields. While a similar reaction with aliphatic amines is applicable for the synthesis of substituted pyrazines, SnCl 2 ·2H 2 O permits versatility in the solvent-free reaction of α-hydroxy ketones with ammonium acetate to give the corresponding substituted pyrazines in good to excellent yields.

  各种苯胺与α-羟基酮在SnCl 2 ·2H 2 O 催化下的无溶剂反应以优异的产率提供了α-氨基酮。虽然与脂肪胺的类似反应适用于合成取代的吡嗪，但 SnCl 2 ·2H 2 O 在 α-羟基酮与乙酸铵的无溶剂反应中具有多功能性，以良好到极好的产率得到相应的取代吡嗪。
• Phosphine Supported Ruthenium Nanoparticle Catalyzed Synthesis of Substituted Pyrazines and Imidazoles from α-Diketones
  作者：Prasad Ganji、Piet W. N. M. van Leeuwen

  DOI：10.1021/acs.joc.6b03032

  日期：2017.2.3

  pyrazines and imidazoles starting from α-diketones using phosphine supported ruthenium nanoparticles (RuNPs) as catalysts. Ruthenium nanoparticles Ru1–Ru4 supported with different phosphines such as dbdocphos, dppp, DPEphos, and Xantphos are screened, of which Ru1 and Ru4 are found to be the most active. Interestingly, aryl-substituted and alkyl-substituted α-diketones produced different products: namely

  已经开发出一种新的方法，以膦为载体的钌纳米颗粒（RuNPs）作为催化剂，从α-二酮开始合成高度取代的氮杂环，例如吡嗪和咪唑。筛选了负载有不同膦（如dbdocphos，dppp，DPEphos和Xantphos）的钌纳米颗粒Ru1 - Ru4，其中Ru1和Ru4具有最强的活性。有趣的是，芳基取代的α-二酮和烷基取代的α-二酮分别产生不同的产物：即吡嗪和咪唑。该反应方法已应用于关键中间体（2m）的海洋细胞毒性天然产物Dragmacidin B和雌激素受体（2l）。这项工作代表了RuNPs制备的吡嗪的第一个实例。
• Tetraphenylpyrazine-based AIEgens: facile preparation and tunable light emission
  作者：Ming Chen、Lingzhi Li、Han Nie、Jiaqi Tong、Lulin Yan、Bin Xu、Jing Zhi Sun、Wenjing Tian、Zujin Zhao、Anjun Qin、Ben Zhong Tang

  DOI：10.1039/c4sc03365e

  日期：——

  Structurally new AIEgens with tunable emission based on tetraphenylpyrazine were rationally designed and readily prepared.

  基于四苯基吡嗪的可调发射的结构新型AIE原料被合理设计并轻松制备。
• Chiral compound for induction of circularly polarized luminescence from achiral luminogens
  申请人：THE HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US11332662B2

  公开（公告）日：2022-05-17

  The present subject matter relates to a fluorescent compound having aggregation-induced emission (AIE) characteristics. The compound can undergo spontaneous hierarchical self-assembly from a vesicle to a helical fiber in the aggregate state. A composition capable of providing circularly polarized luminescence can include the fluorescent compound and at least one additional compound selected from the group consisting of an aggregation-caused quenching luminogen and an aggregation-induced emission luminogen.

  本主题涉及一种具有聚集诱导发射（AIE）特性的荧光化合物。该化合物可以在聚集状态下自发地从囊泡分层自组装成螺旋状纤维。能够提供圆偏振发光的组合物可以包括该荧光化合物和至少一种选自由聚集引起的淬灭发光剂和聚集诱导发射发光剂组成的组的附加化合物。