methyl 2-acetyl-3-nitrobenzoate | 7407-52-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetyl-3-nitrobenzoate
• 英文别名: 3-Nitro-2-acetylbenzoesaeure-methylester；2-acetyl-3-nitro-benzoic acid methyl ester；2-Acetyl-3-nitro-benzoesaeure-methylester；Methyl 2-acetyl-3-nitrobenzoate
• CAS: 7407-52-5
• 化学式: C₁₀H₉NO₅
• 分子量: 223.185
• InChiKey: YZSZMFLBRAJYQT-UHFFFAOYSA-N

物化性质

• 熔点：
  81.5 °C
• 沸点：
  379.9±27.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-碘-3-硝基-苯甲酸 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 硫酸 、 mercury(II) sulfate 、 二异丙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 168.0h， 生成 methyl 2-acetyl-3-nitrobenzoate
  参考文献：
  名称：

  5-Nitroisocoumarins from tandem Castro–Stephens coupling—6-endo-dig cyclisation of 2-iodo-3-nitrobenzoic acid and arylethynes and ring-closure of methyl 2-alkynyl-3-nitrobenzoates with electrophiles

  摘要：

  Reaction of 2-iodo-3-nitrobenzoic acid with arylalkynyl copper(I) reagent gave 3-aryl-5-nitroisocoumarins. Castro-Stephens coupling was followed by in situ Cu-catalysed ring-closure. H-1 NMR and X-ray crystallography showed the cyclisations to be 6-endo, contrasting with reports of 5-exo cyclisation of analogous 2-iodobenzoate esters with alkynes. Sonogashira couplings of methyl 2-iodo-3-nitro-benzoate with phenylacetylene and with trimethylsilylacetylene gave the corresponding 2-alkynyl-3-nitrobenzoate esters. With HgSO4, the phenylalkyne underwent 6-endo cyclisation to give 5-nitro-3-phenylisocoumarin. The disubstituted alkyne esters gave 4-phenylselenylisocoumarins with PhSeCl. 5-Nitro-3-phenyl-4-phenylselenylisocoumarin shows significant sterically-driven distortion of the isocoumarin ring. Reaction of methyl 3-nitro-2-phenylethynylbenzoate with ICI gave the 4-iodoisocoumarin. Thus the nitro group tends to direct these electrophile-driven cyclisations towards the 6-endo mode. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.005

文献信息

• Tirouflet, Bulletin de la Societe Scientifique de Bretagne, 1951, vol. 26, p. Sonderheft 5, S. 7, 96
  作者：Tirouflet

  DOI：——

  日期：——
• 5-Nitroisocoumarins from tandem Castro–Stephens coupling—6-endo-dig cyclisation of 2-iodo-3-nitrobenzoic acid and arylethynes and ring-closure of methyl 2-alkynyl-3-nitrobenzoates with electrophiles
  作者：Esther C.Y. Woon、Archana Dhami、Mary F. Mahon、Michael D. Threadgill

  DOI：10.1016/j.tet.2006.03.005

  日期：2006.5

  Reaction of 2-iodo-3-nitrobenzoic acid with arylalkynyl copper(I) reagent gave 3-aryl-5-nitroisocoumarins. Castro-Stephens coupling was followed by in situ Cu-catalysed ring-closure. H-1 NMR and X-ray crystallography showed the cyclisations to be 6-endo, contrasting with reports of 5-exo cyclisation of analogous 2-iodobenzoate esters with alkynes. Sonogashira couplings of methyl 2-iodo-3-nitro-benzoate with phenylacetylene and with trimethylsilylacetylene gave the corresponding 2-alkynyl-3-nitrobenzoate esters. With HgSO4, the phenylalkyne underwent 6-endo cyclisation to give 5-nitro-3-phenylisocoumarin. The disubstituted alkyne esters gave 4-phenylselenylisocoumarins with PhSeCl. 5-Nitro-3-phenyl-4-phenylselenylisocoumarin shows significant sterically-driven distortion of the isocoumarin ring. Reaction of methyl 3-nitro-2-phenylethynylbenzoate with ICI gave the 4-iodoisocoumarin. Thus the nitro group tends to direct these electrophile-driven cyclisations towards the 6-endo mode. (c) 2006 Elsevier Ltd. All rights reserved.