2-(4-bromophenyl)-5-phenylpyrimidine | 174720-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-bromophenyl)-5-phenylpyrimidine
• CAS: 174720-39-9
• 化学式: C₁₆H₁₁BrN₂
• 分子量: 311.181
• InChiKey: UVFIXGWTZRLWMV-UHFFFAOYSA-N

物化性质

• 沸点：
  360.6±42.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)-5-phenylpyrimidine 在 盐酸 、 ammonium hydroxide 、 溶剂黄146 、 copper(I) bromide 、 sodium nitrite 作用下， 反应 28.0h， 生成 2,5-二苯基嘧啶
  参考文献：
  名称：

  Polycyclic rod-shaped azo dyes based on aminophenylpyrimidines

  摘要：

  DOI：

  10.1007/bf01164793
• 作为产物：
  描述：

  3-(dimethylamino)-2-phenylacrolein 、 4-溴苯甲脒盐酸盐水合物 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 2-(4-bromophenyl)-5-phenylpyrimidine
  参考文献：
  名称：

  Heterocyclic Insecticides Acting at the GABA-Gated Chloride Channel: 5-Alkyl-2-arylpyrimidines and -1,3-thiazines

  摘要：

  5-tert-Butyl-2-(4-ethynylphenyl)pyrimidine and the corresponding 2,5-disubstituted-4H-1,3-thiazine block the GABA-gated chloride channel at c.20 and c.200 nM, respectively, measured as 50% inhibition of the binding of 1-(-4-ethynylphenyl)-4-[H-3]propyl-2,6,7-trioxabicyclo[2.22]octane (4'-ethynyl-4-n-[H-3]propylbicycloorthobenzoate; [H-3]EBOB) in house fly and mouse brain membranes, and they are also toxic to topically-treated dies with LD(50) values of 6-27 mu g g(-1) alone and 2-6 mu g g(-1) with piperonyl butoxide (PB) as synergist. In the pyrimidine series, the general pattern of effectiveness of substituents in the 5-position is tert-butyl > isopropyl approximate to cyclohexyl approximate to cyclopropyl > methyl, phenyl and 3- and 4-fluorophenyl, and in the 2-position is 4-ethynylphenyl much greater than 4-bromophenyl. These planar pyrimidines and nearly-planar 4H-1,3-thiazines with 2-ethynylphenyl or 2-bromophenyl and 5-tert-butyl or 5-isopropyl substituents are more effective than the corresponding 6H-1,3-thiazine, 6-oxo-1,3-thiazines and 4,6-dioxo-1,3-thiazine examined, but they are less active than the analogous conformationally flexible trans-1,3-dioxanes and -1,3-dithianes. The heterocyclic moiety confers a region of high electron density and positions the 2- and 5-substituents in a linear or parallel relationship for optimal affinity at the receptor. Two observations indicate that the new pyrimidines and thiazines probably act as chloride channel blockers. First, the poisoning signs are identical to those of EBOB in both mice and house flies. Second, each of the pyrimidines, thiazines and dioxanes falls on the same correlation line for inhibition of [H-3]EBOB binding and toxicity to house flies (with PB) as that obtained earlier for EBOB analogs, dithianes and polychlorocycloalkanes, suggesting that they all act at the same or closely coupled binding sites in the GABA-gated chloride channel.

  DOI：

  10.1002/(sici)1096-9063(199603)46:3<237::aid-ps359>3.0.co;2-p

文献信息

• 一种含有嘧啶或吡嗪或三嗪基团的苯并茚并芴 衍生物及应用
  申请人：昆山维信诺显示技术有限公司

  公开号：CN103570628B

  公开（公告）日：2016-01-20

  本发明提供了一种新型化合物，其结构用式(I)表示。其中R1至R5分别独立选自C1～C20的脂肪族烷基或C6～C20的芳香族基团；Ar选自C4～C30的芳环、C4～C30的含N杂环、C4～C30的稠合杂环芳烃、C4～C30的芳氨基或C4～C30的芳氧基；n为1或2；A1至A4为N原子或C原子；当A1、A3同时为N原子时，A2和A4为C原子；或者，当A1、A4同时为N原子时，A2和A3为C原子；或者，当A2、A4同时为N原子时，A1和A3为C原子；或者，当A3、A4同时为N原子时，A1和A2为C原子；或者，A1、A3、A4同时为N原子时，A2为C原子；L为单键或C6～C10的芳环或C4～C10的含N杂环。该类化合物在有机电致发光器件中用作电子传输层材料或发光主体材料。
• 以氮杂苯为核心的化合物及其在有机电致发 光器件上的应用
  申请人：中节能万润股份有限公司

  公开号：CN107880031B

  公开（公告）日：2021-03-02

  本发明涉及一种以氮杂苯为核心的化合物及其在有机电致发光器件上的应用，该化合物以氮杂苯为核心，具有分子间不易结晶、不易聚集、具有良好成膜性的特点。本发明化合物作为有机电致发光器件的发光层材料使用时，器件的电流效率，功率效率和外量子效率均得到很大改善；同时，对于器件寿命提升非常明显。
• Organic light-emitting compound and organic electroluminescent device using same
  申请人：DOOSAN CORPORATION

  公开号：US10038146B2

  公开（公告）日：2018-07-31

  The present invention relates to a novel indole-based compound having superior hole injection and transport capabilities, light-emitting capabilities, and the like, and an organic electroluminescent device which comprises the indole-based compound in one or more organic layers thereof so as to thereby achieve improved characteristics, such as light-emitting efficiency, driving voltage, and lifespan characteristics.

  本发明涉及一种新型吲哚基化合物，该化合物具有优异的空穴注入和传输能力、发光能力等，还涉及一种有机电致发光器件，该器件在其一个或多个有机层中包含该吲哚基化合物，从而获得更好的特性，如发光效率、驱动电压和寿命特性。
• [EN] ORGANIC ELECTROLUMINESCENT DEVICE<br/>[FR] DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE
  申请人：DOOSAN CORP

  公开号：WO2014065498A1

  公开（公告）日：2014-05-01

  본 발명은 유기 전계 발광 소자에 관한 것으로, 인돌계 화합물과 이리듐 화합물을 각각 호스트/도펀트 물질로 사용한 발광층을 유기 전계 발광 소자에 도입함으로써 발광효율, 구동 전압 및 수명 등의 특성이 향상된 유기 전계 발광 소자를 제공할 수 있다.
• Heterocyclic Insecticides Acting at the GABA-Gated Chloride Channel: 5-Alkyl-2-arylpyrimidines and -1,3-thiazines
  作者：David A. Pulman、Ian H. Smith、John P. Larkin、John E. Casida

  DOI：10.1002/(sici)1096-9063(199603)46:3<237::aid-ps359>3.0.co;2-p

  日期：1996.3

  5-tert-Butyl-2-(4-ethynylphenyl)pyrimidine and the corresponding 2,5-disubstituted-4H-1,3-thiazine block the GABA-gated chloride channel at c.20 and c.200 nM, respectively, measured as 50% inhibition of the binding of 1-(-4-ethynylphenyl)-4-[H-3]propyl-2,6,7-trioxabicyclo[2.22]octane (4'-ethynyl-4-n-[H-3]propylbicycloorthobenzoate; [H-3]EBOB) in house fly and mouse brain membranes, and they are also toxic to topically-treated dies with LD(50) values of 6-27 mu g g(-1) alone and 2-6 mu g g(-1) with piperonyl butoxide (PB) as synergist. In the pyrimidine series, the general pattern of effectiveness of substituents in the 5-position is tert-butyl > isopropyl approximate to cyclohexyl approximate to cyclopropyl > methyl, phenyl and 3- and 4-fluorophenyl, and in the 2-position is 4-ethynylphenyl much greater than 4-bromophenyl. These planar pyrimidines and nearly-planar 4H-1,3-thiazines with 2-ethynylphenyl or 2-bromophenyl and 5-tert-butyl or 5-isopropyl substituents are more effective than the corresponding 6H-1,3-thiazine, 6-oxo-1,3-thiazines and 4,6-dioxo-1,3-thiazine examined, but they are less active than the analogous conformationally flexible trans-1,3-dioxanes and -1,3-dithianes. The heterocyclic moiety confers a region of high electron density and positions the 2- and 5-substituents in a linear or parallel relationship for optimal affinity at the receptor. Two observations indicate that the new pyrimidines and thiazines probably act as chloride channel blockers. First, the poisoning signs are identical to those of EBOB in both mice and house flies. Second, each of the pyrimidines, thiazines and dioxanes falls on the same correlation line for inhibition of [H-3]EBOB binding and toxicity to house flies (with PB) as that obtained earlier for EBOB analogs, dithianes and polychlorocycloalkanes, suggesting that they all act at the same or closely coupled binding sites in the GABA-gated chloride channel.