2'-(2-nitrobenzoyloxy)acetophenone | 84634-60-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 2'-(2-nitrobenzoyloxy)acetophenone
• 英文别名: 1-[2-(2-nitro-benzoyloxy)-phenyl]-ethanone；1-[2-(2-Nitro-benzoyloxy)-phenyl]-aethanon；Ethanone, 1-[2-[(nitrobenzoyl)oxy]phenyl]-；(2-acetylphenyl) 2-nitrobenzoate
• CAS: 84634-60-6
• 化学式: C₁₅H₁₁NO₅
• 分子量: 285.256
• InChiKey: GDIYLFJXKRHPBN-UHFFFAOYSA-N

物化性质

• 熔点：
  93-94 °C(Solv: ethanol (64-17-5))
• 沸点：
  503.1±35.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-nitrobenzoyloxy)acetophenone 在 氢氧化钾 作用下， 以 吡啶 为溶剂， 生成 1-(2-羟基苯基)-3-(2-硝基苯基)丙烷-1,3-二酮
  参考文献：
  名称：

  Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor

  摘要：

  A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00343-0
• 作为产物：
  描述：

  邻硝基苯甲酸 、 2'-羟基苯乙酮 在 POCl₂ 作用下， 以 吡啶 为溶剂， 反应 3.0h， 以43%的产率得到2'-(2-nitrobenzoyloxy)acetophenone
  参考文献：
  名称：

  Efficient Synthesis of Nitroflavones by Cyclodehydrogenation of 2′-Hydroxychalcones and by the Baker-Venkataraman Method

  摘要：

  Several nitroflavone derivatives were synthesized by cyclodehydrogenation of 2'-hydroxychalcones and by the Baker-Venkataraman approach, starting from 2'-hydroxyacetophenones and benzoic acid derivatives. Nitroflavones synthesised by the first synthetic approach were obtained in better global yields than those obtained by the later method. The structures of all new compounds were elucidated by microanalyses, 1D and 2D NMR, IR, and mass spectroscopic measurements.

  DOI：

  10.1007/s00706-006-0550-9

文献信息

• Dunne et al., Journal of the Chemical Society, 1950, p. 1252,1257
  作者：Dunne et al.

  DOI：——

  日期：——
• Doyle et al., Scientific Proceedings of the Royal Dublin Society, 1948, vol. 24, p. 291,299
  作者：Doyle et al.

  DOI：——

  日期：——
• Srivastava; Satsangi; Kishore, Arzneimittel-Forschung/Drug Research, 1982, vol. 32, # 12, p. 1512 - 1514
  作者：Srivastava、Satsangi、Kishore

  DOI：——

  日期：——
• Lin; Hoch, Arzneimittel-Forschung/Drug Research, 1984, vol. 34, # 5, p. 640 - 642
  作者：Lin、Hoch

  DOI：——

  日期：——
• 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.