2,5-bis-methyl-3,6-bis-(4'-methoxyphenyl)-pyrazine | 124235-34-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-bis-methyl-3,6-bis-(4'-methoxyphenyl)-pyrazine
• 英文别名: 2,5-dimethyl-3,6-bis(4-methoxyphenyl)pyrazine；2,5-Dimethyl-3,6-bis-(4-methoxyphenyl)-pyrazin；2,5-bis-(4-methoxy-phenyl)-3,6-dimethyl-pyrazine；2,5-Bis-(4-methoxy-phenyl)-3,6-dimethyl-pyrazin；2,5-Bis(4-methoxyphenyl)-3,6-dimethylpyrazine；2,5-bis(4-methoxyphenyl)-3,6-dimethylpyrazine
• CAS: 124235-34-3
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: GRTXTZSGSRCEFE-UHFFFAOYSA-N

物化性质

• 熔点：
  1967 °C
• 沸点：
  430.3±45.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-bis-methyl-3,6-bis-(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88%的产率得到4-[5-(4-Hydroxyphenyl)-3,6-dimethylpyrazin-2-yl]phenol
  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：

  4'-methoxy-2-aminopropiophenone hydrochloride 生成 2,5-bis-methyl-3,6-bis-(4'-methoxyphenyl)-pyrazine
  参考文献：
  名称：

  Tiffeneau; Levy; Ditz, Bulletin de la Societe Chimique de France, 1935, vol. <5> 2, p. 1855,1862

  摘要：

  DOI：

文献信息

• Diaryldistyrylpyrazines: Solvatochromic and Acidochromic Fluorophores
  作者：Volker Schmitt、Sebastian Moschel、Heiner Detert

  DOI：10.1002/ejoc.201300463

  日期：2013.9

  Diaryldimethylpyrazines are the starting materials for the synthesis of C2-symmetric donor- or acceptor-substituted distyrylpyrazines. The optical properties of these cruciform-shaped dyes are dominated by the distyrylpyrazine units; the photophysics is controlled by the styryl substitution, the diaryl substituents on the central pyrazine only having a small effect. Protonation occurs on the pyrazine

  二芳基二甲基吡嗪是合成 C2 对称供体或受体取代的二苯乙烯基吡嗪的起始材料。这些十字形染料的光学性质主要由二苯乙烯基吡嗪单元决定；光物理受苯乙烯基取代控制，中心吡嗪上的二芳基取代基仅具有很小的影响。吡嗪和/或侧链胺或吖嗪发生质子化，从而改变吸收和发射特性。浅色和红色以及荧光猝灭取决于末端取代基的性质。这一点，以及荧光的显着正溶剂化变色，允许对环境的 pH 值和极性进行光学传感。
• Estrogenic diazenes: heterocyclic non-steroidal estrogens of unusual structure with selectivity for estrogen receptor subtypes
  作者：Usha Ghosh、Deshanie Ganessunker、Viswajanani J Sattigeri、Kathryn E Carlson、Deborah J Mortensen、Benita S Katzenellenbogen、John A Katzenellenbogen

  DOI：10.1016/s0968-0896(02)00309-7

  日期：2003.2

  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.
• Tiffeneau; Levy; Ditz, Bulletin de la Societe Chimique de France, 1935, vol. <5> 2, p. 1855,1862
  作者：Tiffeneau、Levy、Ditz

  DOI：——

  日期：——