(E)-3-(p-tolylhydrazono)-2-butanone | 136984-61-7

• 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: (E)-3-(p-tolylhydrazono)-2-butanone
• 英文别名: butane-2,3-dione-mono-p-tolylhydrazone；Diacetyl-mono-p-tolylhydrazon；Butan-2,3-dion-mono-p-tolylhydrazon；(3E)-3-[(4-methylphenyl)hydrazinylidene]butan-2-one
• CAS: 136984-61-7
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: HRLTXQRHSMALTO-FMIVXFBMSA-N

物化性质

• 沸点：
  294.0±33.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  41.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(p-tolylhydrazono)-2-butanone 、 碘甲烷 以 二甲基亚砜 为溶剂， 生成 (E)-3-(N-methyl-N-p-tolylhydrazono)-2-butanone
  参考文献：
  名称：

  An easy access to 2-oxohydrazones via electrophilic α-p-tolylhydrazonylation of ketone enolates with tert-butyl p-tolylazo sulfide

  摘要：

  The title reaction conveniently furnishes, as the sole or main products, alpha-(p-tolylhydrazono)ketones or their N-methylderivatives (H+ or Mel quenching of the final mixture, respectively). Although the method fails with ketones having a secondary alkyl group bonded to the carbonyl, yields are otherwise more than satisfactory and particular interest is attached to the hydrazonylation of the methyl group in methyl ketones.

  DOI：

  10.1016/s0040-4020(01)89426-6
• 作为产物：
  描述：

  (Z)-(4-methylphenyl)azo tert-butyl sulfide 以87%的产率得到
  参考文献：
  名称：

  DellErba Carlo, Novi Marino, Petrillo Giovanni, Tavani Cinzia, Tetrahedron, 50 (1994) N 38, S 11239-11248

  摘要：

  DOI：

文献信息

• Japp; Klingemann, Justus Liebigs Annalen der Chemie, 1888, vol. 247, p. 211,222
  作者：Japp、Klingemann

  DOI：——

  日期：——
• Addition of semidione radicals to arenediazonium ions: synthesis of 1,1-diacyl-2-arylhydrazines
  作者：Angelo Clerici、Ombretta Porta

  DOI：10.1021/jo00024a021

  日期：1991.11

  The alpha-dicarbonyl compounds 1 are selectively reduced to semidione radicals 2 by aqueous Ti3+, via inner-sphere electron transfer (ET). When an equimolar amount of an arenediazonium salt (3) is present, 2 adds to the nitrogen-nitrogen triple bond of 3 to afford the intermediate azo radical cation C, which, depending on the nature of the para substituent of the N-phenyl ring, undergoes rearrangement to a 1,1-diacyl-2-arylhydrazine (4) or preferentially reduction to a hydrazone (5). A mechanism that accounts for both the rearrangement and the substituent effects that are observed is proposed.
• Favrel, Bulletin de la Societe Chimique de France, 1902, vol. <3> 27, p. 318
  作者：Favrel

  DOI：——

  日期：——
• Gonzalez, Asensio, Synthetic Communications, 1988, vol. 18, # 11, p. 1225 - 1230
  作者：Gonzalez, Asensio

  DOI：——

  日期：——
• GONZALEZ, ASENSIO, SYNTH. COMMUN., 18,(1988) N 11, 1225-1229
  作者：GONZALEZ, ASENSIO

  DOI：——

  日期：——