8-Bromo-6-chloro-2-(4-methoxyphenyl)-3-methylidenechromen-4-one | 927884-83-1

• 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-methoxyphenyl)-3-methylidenechromen-4-one
• CAS: 927884-83-1
• 化学式: C₁₇H₁₂BrClO₃
• 分子量: 379.637
• InChiKey: ZHZCZMBTUMVJIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-Bromo-6-chloro-2-(4-methoxyphenyl)-3-methylidenechromen-4-one 在 selenium(IV) oxide 、 双三氟甲烷磺酰亚胺 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 3-((benzyloxycarbonylamino)methyl)-8-bromo-6-chloro-2-(4-methoxyphenyl)-chromone
  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：

  (E)-1-(3-bromo-5-chloro-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 在 盐酸 、 盐酸二甲胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.5h， 生成 8-Bromo-6-chloro-2-(4-methoxyphenyl)-3-methylidenechromen-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

文献信息

• Synthesis of 3-Aminomethyl-2-aryl- 8-bromo-6-chlorochromones
  作者：Erik A. A. Wallén、Kristian Dahlén、Morten Grøtli、Kristina Luthman

  DOI：10.1021/ol062478z

  日期：2007.2.1

  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.