2-Methyl-3-(2-nitro-benzoyl)-chromen-4-one | 864433-01-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 2-Methyl-3-(2-nitro-benzoyl)-chromen-4-one
• 英文别名: 2-Methyl-3-(2-nitrobenzoyl)chromen-4-one；2-methyl-3-(2-nitrobenzoyl)chromen-4-one
• CAS: 864433-01-2
• 化学式: C₁₇H₁₁NO₅
• 分子量: 309.278
• InChiKey: GKAAGNYUPRIFNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Methyl-3-(2-nitro-benzoyl)-chromen-4-one 在 sodium tetrahydroborate 作用下， 以 吡啶 为溶剂， 生成 3-[1-Hydroxy-1-(2-nitro-phenyl)-meth-(Z)-ylidene]-2-methyl-chroman-4-one
  参考文献：
  名称：

  Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones

  摘要：

  3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.058
• 作为产物：
  描述：

  2'-(2-nitrobenzoyloxy)acetophenone 在 氢氧化钾 、 sodium acetate 作用下， 以 吡啶 为溶剂， 生成 2-Methyl-3-(2-nitro-benzoyl)-chromen-4-one
  参考文献：
  名称：

  Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones

  摘要：

  3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.058

文献信息

• Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones
  作者：David S. Clarke、Christopher D. Gabbutt、John D. Hepworth、B. Mark Heron

  DOI：10.1016/j.tetlet.2005.06.058

  日期：2005.8

  3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate reduction with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The reduction is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This reduction-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones. (c) 2005 Elsevier Ltd. All rights reserved.