8-bromo-6-chloro-2-(4-trifluoromethylphenyl)-chroman-4-one | 927884-81-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 8-bromo-6-chloro-2-(4-trifluoromethylphenyl)-chroman-4-one
• 英文别名: 8-Bromo-6-chloro-2-[4-(trifluoromethyl)phenyl]-2,3-dihydrochromen-4-one
• CAS: 927884-81-9
• 化学式: C₁₆H₉BrClF₃O₂
• 分子量: 405.598
• InChiKey: MREVPFKWWVZOJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  121-122 °C
• 沸点：
  481.1±45.0 °C(Predicted)
• 密度：
  1.624±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-bromo-6-chloro-2-(4-trifluoromethylphenyl)-chroman-4-one 在 盐酸二甲胺 、 双三氟甲烷磺酰亚胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 0.17h， 生成 3-((benzyloxycarbonylamino)methyl)-8-bromo-6-chloro-2-(4-trifluoromethylphenyl)-chroman-4-one
  参考文献：
  名称：

  Synthesis of 3-Aminomethyl-2-aryl- 8-bromo-6-chlorochromones

  摘要：

  An efficient synthetic route to Cbz-protected 3-aminomethyl-2-aryl-8-bromo-6-chlorochromones has been developed. 3-Aryl-1-(3-bromo-5-chloro-2-hydroxyphenyl)-2-propen-1-one or 2-aryl-8-bromo-6-chlorochroman-4-one could be reacted under Mannich conditions yielding 2-aryl-8-bromo-6-chloro-3-methylenechroman-4-one, which was further converted to the target compound via an aza-Michael reaction followed by an SeO2 oxidation. This procedure represents a new method to introduce a primary aminomethyl group at the 3-position of a 2-arylchromone scaffold. The Cbz-protected 3-aminomethyl-2-aryl-8-bromo-6-chlorochromones can, e.g., be used in the synthesis of chromone-based beta-turn peptidomimetics.

  DOI：

  10.1021/ol062478z
• 作为产物：
  描述：

  3'-溴-5'-氯-2'-羟基苯乙酮 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 8-bromo-6-chloro-2-(4-trifluoromethylphenyl)-chroman-4-one
  参考文献：
  名称：

  Synthesis of 3-Aminomethyl-2-aryl- 8-bromo-6-chlorochromones

  摘要：

  An efficient synthetic route to Cbz-protected 3-aminomethyl-2-aryl-8-bromo-6-chlorochromones has been developed. 3-Aryl-1-(3-bromo-5-chloro-2-hydroxyphenyl)-2-propen-1-one or 2-aryl-8-bromo-6-chlorochroman-4-one could be reacted under Mannich conditions yielding 2-aryl-8-bromo-6-chloro-3-methylenechroman-4-one, which was further converted to the target compound via an aza-Michael reaction followed by an SeO2 oxidation. This procedure represents a new method to introduce a primary aminomethyl group at the 3-position of a 2-arylchromone scaffold. The Cbz-protected 3-aminomethyl-2-aryl-8-bromo-6-chlorochromones can, e.g., be used in the synthesis of chromone-based beta-turn peptidomimetics.

  DOI：

  10.1021/ol062478z