1-(4-bromophenyl)-2-(pyridin-3-yl)ethanone | 1233693-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-bromophenyl)-2-(pyridin-3-yl)ethanone
• 英文别名: 1-(4-Bromophenyl)-2-pyridin-3-ylethanone；1-(4-bromophenyl)-2-pyridin-3-ylethanone
• CAS: 1233693-27-0
• 化学式: C₁₃H₁₀BrNO
• 分子量: 276.132
• InChiKey: ZBJHADMLJXLAJO-UHFFFAOYSA-N

物化性质

• 沸点：
  411.7±30.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-2-(pyridin-3-yl)ethanone 、 4-氟苯硼酸 在 四丁基溴化铵 、 palladium diacetate 、 sodium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 4.0h， 以42%的产率得到1-(4'-fluorobiphenyl-4-yl)-2-(pyridin-3-yl)ethanone
  参考文献：
  名称：

  Isopropylidene Substitution Increases Activity and Selectivity of Biphenylmethylene 4-Pyridine Type CYP17 Inhibitors

  摘要：

  GYP 17 inhibition is a promising therapy for prostate cancer (PC) because proliferation of 80% of PC depends on androgen stimulation. Introduction of isopropylidene substituents onto the linker of biphenylmethylene 4-pyridines resulted in several strong GYP 17 inhibitors, which were more potent and selective, regarding GYP 11B1, 11B2, 19 and 3A4, than the drug candidate abiraterone.

  DOI：

  10.1021/jm100400a
• 作为产物：
  描述：

  3-甲基吡啶 、 对溴苯甲酸甲酯 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以12%的产率得到1-(4-bromophenyl)-2-(pyridin-3-yl)ethanone
  参考文献：
  名称：

  Isopropylidene Substitution Increases Activity and Selectivity of Biphenylmethylene 4-Pyridine Type CYP17 Inhibitors

  摘要：

  GYP 17 inhibition is a promising therapy for prostate cancer (PC) because proliferation of 80% of PC depends on androgen stimulation. Introduction of isopropylidene substituents onto the linker of biphenylmethylene 4-pyridines resulted in several strong GYP 17 inhibitors, which were more potent and selective, regarding GYP 11B1, 11B2, 19 and 3A4, than the drug candidate abiraterone.

  DOI：

  10.1021/jm100400a

文献信息

• Palladium-Catalyzed Direct α-C(sp3) Heteroarylation of Ketones under Microwave Irradiation
  作者：Andrew Quillen、Quynh Nguyen、Matthew Neiser、Kara Lindsay、Alexander Rosen、Stephen Ramirez、Stefana Costan、Nathan Johnson、Thuy Donna Do、Oscar Rodriguez、Diego Rivera、Abdurrahman Atesin、Tülay Aygan Ateşin、Lili Ma

  DOI：10.1021/acs.joc.9b00446

  日期：2019.6.21

  building blocks in medicinal chemistry and chemical industry. A palladium-catalyzed direct α-C(sp3) heteroarylation of ketones under microwave irradiation is developed and reported in this study. Under optimized conditions, twenty-eight (28) heteroarylated ketones were prepared in this study to demonstrate the substrate scope of this reaction. The ground-state optimized structure of Pd(0) active catalyst

  杂芳基化合物是药物化学和化学工业中有价值的组成部分。在这项研究中开发并报道了钯催化的在微波辐射下酮的直接α-C（sp3）杂芳基化反应。在优化的条件下，本研究中制备了二十八（28）个杂芳基化酮，以证明该反应的底物范围。研究了用2-二环己基膦基2'，4'，6'-三异丙基联苯（XPhos）在甲苯中的Pd（0）活性催化剂的基态优化结构，并研究了其与3-溴吡啶和苯乙酮的反应产物。原子密度泛函理论。该研究为钯催化体系设计产生杂芳基化合物提供了有见地的信息。
• Isopropylidene Substitution Increases Activity and Selectivity of Biphenylmethylene 4-Pyridine Type CYP17 Inhibitors
  作者：Qingzhong Hu、Lina Yin、Carsten Jagusch、Ulrike E. Hille、Rolf W. Hartmann

  DOI：10.1021/jm100400a

  日期：2010.7.8

  GYP 17 inhibition is a promising therapy for prostate cancer (PC) because proliferation of 80% of PC depends on androgen stimulation. Introduction of isopropylidene substituents onto the linker of biphenylmethylene 4-pyridines resulted in several strong GYP 17 inhibitors, which were more potent and selective, regarding GYP 11B1, 11B2, 19 and 3A4, than the drug candidate abiraterone.