2-methyl-2-pentenal (2,4-dinitrophenyl)hydrazone | 1572-64-1

• 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: 2-methyl-2-pentenal (2,4-dinitrophenyl)hydrazone
• 英文别名: α-Methyl-β-ethyl-acrolein-2,4-dinitrophenylhydrazon；3-Ethyl-2-methyl-acrolein-(1)-(2,4-dinitro-phenylhydrazon)；2-Methyl-penten-(2)-al-(1)-(2,4-dinitro-phenylhydrazon)；2-Methyl-penten-(2)-al-(1)-(2,4-dinitrophenylhydrazon)；2-Methyl-pent-2-en-1-on-(2,4-dinitro-phenylhydrazon)；2-Methyl-pent-2-en-1-al-(2,4-dinitrophenylhydrazon)；N-(2-methylpent-2-enylideneamino)-2,4-dinitroaniline
• CAS: 1572-64-1
• 化学式: C₁₂H₁₄N₄O₄
• 分子量: 278.268
• InChiKey: HMWKNWMAOQBCLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-methyl-2-pentenal (2,4-dinitrophenyl)hydrazone 在 溴 作用下， 生成 2.3-Dibrom-2-methyl-pentanal-(1)-<2.4-dinitro-phenylhydrazon>
  参考文献：
  名称：

  Spare,C.-G.; Virtanen,A.I., Acta Chemica Scandinavica (1947), 1961, vol. 15, p. 1280 - 1284

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基-2-戊烯醛 、 3-hydroxyl-2-methylpentanal 、 3-羟基-2,4-二甲基-4-庚烯醛 、 丙醛 、 2,4-二硝基苯肼 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.33h， 生成 3-Hydroxy-2-methylpentanal 2-(2,4-dinitrophenyl)hydrazone 、 、 propanal 2,4-dinitrophenyl hydrazone 、 2-methyl-2-pentenal (2,4-dinitrophenyl)hydrazone
  参考文献：
  名称：

  Self- and Cross-Aldol Condensation of Propanal Catalyzed by Anion-Exchange Resins in Aqueous Media

  摘要：

  Carbon-carbon bond formation using strong and weak anion-exchange resins as green catalysts for self- and cross-aldol condensation of propanal in aqueous media was investigated. The reaction pathway followed the route of aldol condensation to a beta-hydroxy aldehyde and dehydration to an alpha,beta-unsaturated aldehyde. The resulting products were further converted to hemiacetal, and/or acetal moieties, which were confirmed by FT-IR and NMR. In self-condensation using strong anion-exchange resin, 97% conversion of propanal was achieved with 95% selectivity to 2-methyl-2-pentenal within 1 h using 0.4 g/mL resin at 35 degrees C. The conversion and selectivity using weak anion exchanger was lower. During cross-aldol condensation of propanal with formaldehyde, 3-hydroxy-2-methyl-2-hydroxymethylpropanal was obtained as the main product through first and second cross-condensation followed by hydration reaction in acidic aqueous conditions. The strong anion-exchange resin provided maximal propanal conversion of 80.4% to the product with 72.4% selectivity after 7 h reaction at 35 degrees C and resin concentration of 1.2 g/mL. Using weak anion-exchange resin, the optimal conversion of propanal was 89.9% after 24 h at 0.8 g/mL resin and 35 degrees C, and the main product was 3-hydroxy-2-methylpropanal by first cross-aldol condensation along with relatively minor amounts of methacrolein and 3-hydroxy-2-methyl-2-hydroxymethylpropanal.

  DOI：

  10.1021/op200004p

文献信息

• Self- and Cross-Aldol Condensation of Propanal Catalyzed by Anion-Exchange Resins in Aqueous Media
  作者：Sang-Hyun Pyo、Martin Hedström、Stefan Lundmark、Nicola Rehnberg、Rajni Hatti-Kaul

  DOI：10.1021/op200004p

  日期：2011.5.20

  Carbon-carbon bond formation using strong and weak anion-exchange resins as green catalysts for self- and cross-aldol condensation of propanal in aqueous media was investigated. The reaction pathway followed the route of aldol condensation to a beta-hydroxy aldehyde and dehydration to an alpha,beta-unsaturated aldehyde. The resulting products were further converted to hemiacetal, and/or acetal moieties, which were confirmed by FT-IR and NMR. In self-condensation using strong anion-exchange resin, 97% conversion of propanal was achieved with 95% selectivity to 2-methyl-2-pentenal within 1 h using 0.4 g/mL resin at 35 degrees C. The conversion and selectivity using weak anion exchanger was lower. During cross-aldol condensation of propanal with formaldehyde, 3-hydroxy-2-methyl-2-hydroxymethylpropanal was obtained as the main product through first and second cross-condensation followed by hydration reaction in acidic aqueous conditions. The strong anion-exchange resin provided maximal propanal conversion of 80.4% to the product with 72.4% selectivity after 7 h reaction at 35 degrees C and resin concentration of 1.2 g/mL. Using weak anion-exchange resin, the optimal conversion of propanal was 89.9% after 24 h at 0.8 g/mL resin and 35 degrees C, and the main product was 3-hydroxy-2-methylpropanal by first cross-aldol condensation along with relatively minor amounts of methacrolein and 3-hydroxy-2-methyl-2-hydroxymethylpropanal.
• Spare,C.-G.; Virtanen,A.I., Acta Chemica Scandinavica (1947), 1961, vol. 15, p. 1280 - 1284
  作者：Spare,C.-G.、Virtanen,A.I.

  DOI：——

  日期：——