biacetyl monobenzoyl hydrazone | 55590-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: biacetyl monobenzoyl hydrazone
• 英文别名: butane-2,3-dione mono-benzoylhydrazone；benzoic acid-(1-methyl-2-oxo-propylidenehydrazide)；Benzoesaeure-(1-methyl-2-oxo-propylidenhydrazid)；Diacetyl-mono-benzoylhydrazon；N-(3-oxobutan-2-ylideneamino)benzamide
• CAS: 55590-53-9
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: MPBZVUYVAHBRPG-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  biacetyl monobenzoyl hydrazone 在 lead(IV) acetate 、 溶剂黄146 、 二甲基亚砜 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 10.02h， 生成 N-benzoyl-S,S-dimethylsulfoximine
  参考文献：
  名称：

  1,2,3-Triazol-1-imines. 1. The synthesis and lead tetraacetate oxidation of biacetyl benzoylhydrazone arylhydrazones to the novel 2-aryl-N-benzoyl-4,5-dimethyl-1,2,3-triazol-1-imines

  摘要：

  The synthesis and the Pb(OAc)4 oxidation of the mixed bishydrazones of biacetyl 7 was studied. The formation of the novel N-benzoyl-1,2,3-triazol-1-imines 9 from the oxidation of 7 provided support to the proposed in the past mechanism for the oxidation of bis-aroylhydrazones of alpha-dicarbonyl compounds 4. Thermolysis and photolysis of 9a in DMSO was carried out. The results suggested that benzoylnitrene was formed in the photochemical reaction, and therefore compounds such as 9 could serve as non-azide aroyl nitrene precursors. For 9a the results of the X-ray analysis were correlated with charge densities and bond orders gleaned by the MNDO method. Product 9d was alternatively synthesized by the addition of photochemically generated benzoylnitrene to the 1,2,3-triazole 21.

  DOI：

  10.1021/jo00034a013
• 作为产物：
  描述：

  苯甲酰肼 、 2,3-丁二酮 在 水 作用下， 生成 biacetyl monobenzoyl hydrazone
  参考文献：
  名称：

  v. Pechmann; Bauer, Chemische Berichte, 1909, vol. 42, p. 663

  摘要：

  DOI：

文献信息

• Metze, Chemische Berichte, 1955, vol. 88, p. 772,776
  作者：Metze

  DOI：——

  日期：——
• Schmidpeter,A.; Weinmaier,J.H., Angewandte Chemie, 1975, vol. 87, p. 517 - 518
  作者：Schmidpeter,A.、Weinmaier,J.H.

  DOI：——

  日期：——
• v. Pechmann; Bauer, Chemische Berichte, 1909, vol. 42, p. 663
  作者：v. Pechmann、Bauer

  DOI：——

  日期：——
• The Preparation and Lead Tetraacetate Oxidation of Mixed Bisaroyl Hydrazones of Biacetyl to 1-(a-Aroyloxyarylideneamino)-3,5-dimethyl-1,2,3-triazoles
  作者：Constantina P. Hadjiantoniou-Maroulis

  DOI：10.3987/com-98-8350

  日期：——
• 1,2,3-Triazol-1-imines. 1. The synthesis and lead tetraacetate oxidation of biacetyl benzoylhydrazone arylhydrazones to the novel 2-aryl-N-benzoyl-4,5-dimethyl-1,2,3-triazol-1-imines
  作者：C. P. Hadjiantoniou-Maroulis、A. J. Maroulis、A. Terzis、D. Mentzafos

  DOI：10.1021/jo00034a013

  日期：1992.4

  The synthesis and the Pb(OAc)4 oxidation of the mixed bishydrazones of biacetyl 7 was studied. The formation of the novel N-benzoyl-1,2,3-triazol-1-imines 9 from the oxidation of 7 provided support to the proposed in the past mechanism for the oxidation of bis-aroylhydrazones of alpha-dicarbonyl compounds 4. Thermolysis and photolysis of 9a in DMSO was carried out. The results suggested that benzoylnitrene was formed in the photochemical reaction, and therefore compounds such as 9 could serve as non-azide aroyl nitrene precursors. For 9a the results of the X-ray analysis were correlated with charge densities and bond orders gleaned by the MNDO method. Product 9d was alternatively synthesized by the addition of photochemically generated benzoylnitrene to the 1,2,3-triazole 21.