4-bromo-benzaldehyde-(4-nitro-phenylhydrazone) | 5802-78-8

• 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: 4-bromo-benzaldehyde-(4-nitro-phenylhydrazone)
• 英文别名: 4-Brom-benzaldehyd-(4-nitro-phenylhydrazon)；N-[(4-bromophenyl)methylideneamino]-4-nitroaniline
• CAS: 5802-78-8
• 化学式: C₁₃H₁₀BrN₃O₂
• 分子量: 320.145
• InChiKey: RENPHZLBPTWBHU-UHFFFAOYSA-N

物化性质

• 熔点：
  207-208 °C
• 沸点：
  447.8±45.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-benzaldehyde-(4-nitro-phenylhydrazone) 在 ammonium chlorochromate on aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以70%的产率得到对溴苯甲醛
  参考文献：
  名称：

  The Cleavage of p-Nitrophenylhydrazones and Semicarbazones with Ammonium Chlorochromate Adsorbed on Alumina Under Non-Aqueous Conditions

  摘要：

  Deprotection of p-nitrophenylhydrazones and semicarbazones to their parent aldehydes and ketones in good yields has been carried out by using ammonium chlorochromate adsorbed on alumina under mild conditions.

  DOI：

  10.1080/00397919908086086
• 作为产物：
  描述：

  对溴苯甲醛 、 4-硝基苯肼 以 甲醇 为溶剂， 反应 2.0h， 以24%的产率得到4-bromo-benzaldehyde-(4-nitro-phenylhydrazone)
  参考文献：
  名称：

  Synthesis of Substituted 1H-Indazoles from Arynes and Hydrazones

  摘要：

  The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.

  DOI：

  10.1021/jo202598e

文献信息

• Kinetics and mechanism of the reaction of substituted phenylhydrazones with thallium(III) acetate. Reactions of mercury(II) acetate with nitrogen compounds. Part 8
  作者：Richard N. Butler、Gerard J. Morris、Anne M. O'Donohue

  DOI：10.1039/p29810001243

  日期：——

  The reaction of substituted phenylhydrazones with thallium(III) acetate in acetic acid involved an electrophilic attack at the hydrazone amino-NH moiety giving an intermediate which is attacked by solvent at the methine carbon. The Hammett ρ values for substituents in the methine and the N-phenyl rings were –1.05 and –3.6, respectively. Activation thermodynamic parameters ΔEa 17.9, ΔHa 17.2 kcal mol–1

  取代的苯hydr与乙酸th（III）在乙酸中的反应在氨基-NH部分发生亲电攻击，从而制得中间体，该中间体在次甲基碳上被溶剂攻击。次甲基和N-苯基环中取代基的哈米特ρ值分别为–1.05和–3.6。活化热力学参数Δ Ë一个17.9，Δ ħ一个17.2千卡摩尔-1，Δ小号一个-14.65 CALķ -1摩尔-1测量了p氯苯甲醛p-硝基苯hydr。芳族醛芳基hydr的主要产物是N'-乙酰基-N-芳酰基-N'-芳基肼（5）。酮芳基hydr的主要产物是酮的α-乙酰氧基-α-苯基偶氮衍生物（4）。讨论了苯hydr与Hg II，TI III和Pb IV的乙酸酯的反应性出乎意料的差异。
• Synthesis of Polysubstituted Pyrazoles by a Platinum-Catalyzed Sigmatropic Rearrangement/Cyclization Cascade
  作者：Jia-Jie Wen、Hai-Tao Tang、Kai Xiong、Zong-Cang Ding、Zhuang-Ping Zhan

  DOI：10.1021/ol502968c

  日期：2014.11.21

  A highly efficient Pt-catalyzed [3,3] sigmatropic rearrangement/cyclization cascade of N-propargylhydrazones is reported. The process provides expedient access to a variety of highly functionalized pyrazoles. The substrate has good substituted group compatibility, and the bioactive 3-CF3 pyrazoles could be synthesized easily with this method.

  报道了N-炔丙基hydr的高效Pt催化的[3,3]σ重排/环化级联反应。该方法可方便地获得各种高度官能化的吡唑。该底物具有良好的取代基相容性，并且该方法可以容易地合成生物活性3-CF 3吡唑。
• van der Lee, Recueil des Travaux Chimiques des Pays-Bas, 1926, vol. 45, p. 279
  作者：van der Lee

  DOI：——

  日期：——
• The Cleavage of p-Nitrophenylhydrazones and Semicarbazones with Ammonium Chlorochromate Adsorbed on Alumina Under Non-Aqueous Conditions
  作者：Gui-Sheng Zhang、Hui Gong、De-Hong Yang、Mi-Feng Chen

  DOI：10.1080/00397919908086086

  日期：1999.4

  Deprotection of p-nitrophenylhydrazones and semicarbazones to their parent aldehydes and ketones in good yields has been carried out by using ammonium chlorochromate adsorbed on alumina under mild conditions.
• Synthesis of Substituted 1<i>H</i>-Indazoles from Arynes and Hydrazones
  作者：Pan Li、Chunrui Wu、Jingjing Zhao、Donald C. Rogness、Feng Shi

  DOI：10.1021/jo202598e

  日期：2012.4.6

  The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.