2'-(2-nitrocinnamoyloxy)acetophenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-(2-nitrocinnamoyloxy)acetophenone
• 英文别名: (2-acetylphenyl) (E)-3-(2-nitrophenyl)prop-2-enoate
• 化学式: C₁₇H₁₃NO₅
• 分子量: 311.294
• InChiKey: FVBUWNRKEKYLKQ-ZHACJKMWSA-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：
  5
• 环数：
  2.0
• 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'-(2-nitrocinnamoyloxy)acetophenone 在 potassium tert-butylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 生成 (2Z,4E)-3-Hydroxy-1-(2-hydroxy-phenyl)-5-(2-nitro-phenyl)-penta-2,4-dien-1-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'-羟基苯乙酮 、 2-nitrocinnamic acid 在 吡啶 、 三氯氧磷 作用下， 反应 3.0h， 以55%的产率得到2'-(2-nitrocinnamoyloxy)acetophenone
  参考文献：
  名称：

  使用1D和2D NMR光谱对三个系列的2-硝基苯乙烯基色酮进行合成和结构解析。

  摘要：

  尽管2-苯乙烯基色酮本质上是稀缺的，但它们构成一组已显示出显着生物学活性的氧杂环化合物。通过Baker-Venkataraman方法合成了新的硝基-2-苯乙烯基色酮，并使用大量的1D（1H，13C）和2D NMR光谱研究（COSY，HSQC和HMBC实验）完成了结构阐明。

  DOI：

  10.1002/mrc.2472

文献信息

• Synthesis and structure elucidation of three series of nitro-2-styrylchromones using 1D and 2D NMR spectroscopy
  作者：Ana I. R. N. A. Barros、Artur M. S. Silva

  DOI：10.1002/mrc.2472

  日期：2009.10

  heterocyclic compounds which have shown significant biological activities. New nitro-2-styrylchromones have been synthesised by the Baker-Venkataraman method, and the structure elucidation was accomplished using extensive 1D (1H, 13C) and 2D NMR spectroscopic studies (COSY, HSQC and HMBC experiments).

  尽管2-苯乙烯基色酮本质上是稀缺的，但它们构成一组已显示出显着生物学活性的氧杂环化合物。通过Baker-Venkataraman方法合成了新的硝基-2-苯乙烯基色酮，并使用大量的1D（1H，13C）和2D NMR光谱研究（COSY，HSQC和HMBC实验）完成了结构阐明。
• 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.