4-(4-bromophenyl)-6-tert-butyl-2H-chromen-2-one | 863722-27-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 4-(4-bromophenyl)-6-tert-butyl-2H-chromen-2-one
• 英文别名: 4-(4-Bromophenyl)-6-tert-butylchromen-2-one
• CAS: 863722-27-4
• 化学式: C₁₉H₁₇BrO₂
• 分子量: 357.247
• InChiKey: WRPANOLCKCQDRW-UHFFFAOYSA-N

物化性质

• 沸点：
  458.5±45.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-bromophenyl)-6-tert-butyl-2H-chromen-2-one 、 N-甲基-P-氨基苯甲醚 在 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以52%的产率得到6-tert-butyl-4-(4-(N-methylanilino)phenyl)-2H-chromen-2-one
  参考文献：
  名称：

  Sequential Pd(II)−Pd(0) Catalysis for the Rapid Synthesis of Coumarins

  摘要：

  Electrophilic palladium-catalyzed cycloisomerization of brominated aryl propiolates produces brominated coumarins. The brominated cournarins can be diversified by reduction of the Pd(II) catalyst to Pd(O) followed by Suzuki, Sonogashira, Heck, or Hartwig-Buchwald coupling. Thus, a single loading of precatalyst can be used to conduct sequential reactions, allowing the synthesis of functionalized coumarins. Extension of this methodology toward the synthesis of coumarin libraries is discussed.

  DOI：

  10.1021/jo050671l
• 作为产物：
  描述：

  4-(tert-butyl)phenyl 3-(4-bromophenyl)propiolate 在 palladium diacetate 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到4-(4-bromophenyl)-6-tert-butyl-2H-chromen-2-one
  参考文献：
  名称：

  Sequential Pd(II)−Pd(0) Catalysis for the Rapid Synthesis of Coumarins

  摘要：

  Electrophilic palladium-catalyzed cycloisomerization of brominated aryl propiolates produces brominated coumarins. The brominated cournarins can be diversified by reduction of the Pd(II) catalyst to Pd(O) followed by Suzuki, Sonogashira, Heck, or Hartwig-Buchwald coupling. Thus, a single loading of precatalyst can be used to conduct sequential reactions, allowing the synthesis of functionalized coumarins. Extension of this methodology toward the synthesis of coumarin libraries is discussed.

  DOI：

  10.1021/jo050671l

文献信息

• Sequential Pd(II)−Pd(0) Catalysis for the Rapid Synthesis of Coumarins
  作者：Kelin Li、Yibin Zeng、Ben Neuenswander、Jon A. Tunge

  DOI：10.1021/jo050671l

  日期：2005.8.1

  Electrophilic palladium-catalyzed cycloisomerization of brominated aryl propiolates produces brominated coumarins. The brominated cournarins can be diversified by reduction of the Pd(II) catalyst to Pd(O) followed by Suzuki, Sonogashira, Heck, or Hartwig-Buchwald coupling. Thus, a single loading of precatalyst can be used to conduct sequential reactions, allowing the synthesis of functionalized coumarins. Extension of this methodology toward the synthesis of coumarin libraries is discussed.