2-cyclohexenone 2,4-dinitrophenylhydrazone | 1459-31-0

• 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-cyclohexenone 2,4-dinitrophenylhydrazone
• 英文别名: 1-(cyclohex-2-en-1-ylidene)-2-(2,4-dinitrophenyl)hydrazine；cyclohex-2-enone-(2,4-dinitro-phenylhydrazone)；Cyclohex-2-enon-(2,4-dinitro-phenylhydrazon)；Δ²-Cyclohexen-1-on-<2,4-dinitro-phenylhydrazon>；Cyclohex-1-en-3-on-<2,4-dinitro-phenylhydrazon>；1-<2,4-Dinitro-phenylhydrazono>-cyclohexen-(2)；1-(Cyclohex-2-enylidene)-2-(2,4-dinitrophenyl)hydrazine；N-(cyclohex-2-en-1-ylideneamino)-2,4-dinitroaniline
• CAS: 1459-31-0
• 化学式: C₁₂H₁₂N₄O₄
• 分子量: 276.252
• InChiKey: ZMXJLBYYNDEELC-UHFFFAOYSA-N

物化性质

• 熔点：
  167.5-168 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  437.5±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• 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

• 作为产物：
  描述：

  2-环己烯醇 在 ruthenium trichloride 碘苯二乙酸 、 硫酸 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 2.5h， 生成 2-cyclohexenone 2,4-dinitrophenylhydrazone
  参考文献：
  名称：

  高效RuCl 3催化的（二乙酰氧基碘）苯歧化为碘苯和碘代苯；导致醇有效地氧化为羰基化合物

  摘要：

  在室温下，在乙腈水溶液中，在RuCl 3（0.8-1.0 mol％）存在的情况下，（二乙氧基碘）苯（DIB）将伯醇和仲醇选择性氧化为相应的羰基化合物。该反应通过初始瞬时Ru催化的DIB歧化成碘代苯和碘代苯进行，而后者作为对醇的实际化学计量的氧化剂。

  DOI：

  10.1016/j.tetlet.2006.06.100

文献信息

• 2-Iodoxybenzoic acid organosulfonates: preparation, X-ray structure and reactivity of new, powerful hypervalent iodine(v) oxidants
  作者：Mekhman S. Yusubov、Dmitrii Yu. Svitich、Akira Yoshimura、Victor N. Nemykin、Viktor V. Zhdankin

  DOI：10.1039/c3cc47090c

  日期：——

  New powerful hypervalent iodine(V) oxidants, tosylate and mesylate derivatives of 2-iodoxybenzoic acid (IBX), were prepared by the reaction of IBX with the corresponding sulfonic acids. Single crystal X-ray crystallography of the diacetate derivative of IBX-tosylate revealed an unusual heptacoordinated iodine geometry without any significant intermolecular secondary interactions.

  通过IBX与相应的磺酸反应，制得了新的强效高价碘（V）氧化剂，即2-碘氧基苯甲酸（IBX）的甲苯磺酸酯和甲磺酸酯衍生物。IBX-甲苯磺酸酯的二乙酸酯衍生物的单晶X射线晶体学分析显示异常的七配位碘几何结构，没有任何明显的分子间二级相互作用。
• Facile preparation and reactivity of bifunctional ionic liquid-supported hypervalent iodine reagent: a convenient recyclable reagent for catalytic oxidation
  作者：Chenjie Zhu、Akira Yoshimura、Yunyang Wei、Victor N. Nemykin、Viktor V. Zhdankin

  DOI：10.1016/j.tetlet.2012.01.053

  日期：2012.3

  efficient, and recyclable bifunctional catalysts bearing ionic liquid supported (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) and iodoarene moieties were developed and used for environmentally benign catalytic oxidation of alcohols. The reactions using peracetic acid as a green and practical co-oxidant afforded the corresponding carbonyl compounds in high yields under mild conditions and convenient work-up

  开发了带有离子液体负载的（2,2,6,6-四甲基哌啶-1-基）氧基（TEMPO）和碘芳烃基团的新型，高效且可回收的双功能催化剂，并将其用于环境友好的醇催化氧化。使用过氧乙酸作为绿色和实用的助氧化剂的反应在温和的条件下和方便的后处理下以高收率提供了相应的羰基化合物。此外，这些离子液体负载的双官能催化剂可以简单地回收和再利用。
• Copper(I)/ABNO-Catalyzed Aerobic Alcohol Oxidation: Alleviating Steric and Electronic Constraints of Cu/TEMPO Catalyst Systems
  作者：Janelle E. Steves、Shannon S. Stahl

  DOI：10.1021/ja409241h

  日期：2013.10.23

  Cu/TEMPO catalyst systems promote efficient aerobic oxidation of sterically unhindered primary alcohols and electronically activated substrates, but they show reduced reactivity with aliphatic and secondary alcohols. Here, we report a catalyst system, consisting of ((MeO)bpy)Cu-I(OTf) and ABNO ((MeO)bpy = 4,4'-dimethoxy-2,2'-bipyridine; ABNO = 9-azabicyclo[3.3.1]nonane N-oxyl), that mediates aerobic oxidation of all classes of alcohols, including primary and secondary allylic, benzylic, and aliphatic alcohols with nearly equal efficiency. The catalyst exhibits broad functional group compatibility, and most reactions are complete within 1 h at room temperature using ambient air as the source of oxidant.
• Δ²-Cyclohexenone and Related Substances
  作者：Frank C. Whitmore、G. W. Pedlow

  DOI：10.1021/ja01848a033

  日期：1941.3
• Some Reactions of Δ²-Cyclohexenone, Including the Synthesis of Bicyclo(2,2,2)-octanedione-2,6
  作者：Paul D. Bartlett、G. Forrest Woods

  DOI：10.1021/ja01868a014

  日期：1940.11

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