3-((benzyloxycarbonylamino)methyl)-8-bromo-6-chloro-2-(4-methoxyphenyl)-chromone | 927884-89-7

• 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: 3-((benzyloxycarbonylamino)methyl)-8-bromo-6-chloro-2-(4-methoxyphenyl)-chromone
• 英文别名: benzyl N-[[8-bromo-6-chloro-2-(4-methoxyphenyl)-4-oxochromen-3-yl]methyl]carbamate
• CAS: 927884-89-7
• 化学式: C₂₅H₁₉BrClNO₅
• 分子量: 528.787
• InChiKey: MJONYEXTEHUWFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-((benzyloxycarbonylamino)methyl)-8-bromo-6-chloro-2-(4-methoxyphenyl)-chromone 在 tris(dibenzylideneacetone)dipalladium (0) 四(三苯基膦)钯 、 三叔丁基膦 、 cesium fluoride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.0h， 生成 8-benzyl-3-((benzyloxycarbonylamino)methyl)-2-(4-methoxyphenyl)-6-vinyl-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：

  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

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.