4-nitro-benzaldehyde phenylhydrazone | 2829-27-8

• 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-nitro-benzaldehyde phenylhydrazone
• 英文别名: 1-(4-nitrobenzylidene)-2-phenylhydrazine；p-Nitrobenzaldehyde phenylhydrazone；N-[(4-nitrophenyl)methylideneamino]aniline
• CAS: 2829-27-8
• 化学式: C₁₃H₁₁N₃O₂
• 分子量: 241.249
• InChiKey: IXMQSJMHAYPXSV-UHFFFAOYSA-N

物化性质

• 熔点：
  194 °C(Solv: acetic acid (64-19-7))
• 沸点：
  408.0±37.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 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-nitro-benzaldehyde phenylhydrazone 在 2,6-dicarboxypyridinium fluorochromate 作用下， 反应 0.33h， 以88%的产率得到对硝基苯甲醛
  参考文献：
  名称：

  2,6-二羧基吡啶鎓氟铬酸盐：在无溶剂条件下将肟、苯腙和氨基脲氧化脱保护成相应羰基化合物的温和高效试剂

  摘要：

  制备了2,6-二羧基氟铬酸吡啶鎓作为一种新型、快速、高效的试剂，用于在室温下无溶剂条件下将肟、苯腙和氨基脲氧化脱保护为其羰基类似物。

  DOI：

  10.1002/jccs.200500140
• 作为产物：
  描述：

  N-[叔丁基(二苯基)甲硅烷基]-1-苯基甲胺 在 次氯酸叔丁酯 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 94.5h， 生成 4-nitro-benzaldehyde phenylhydrazone
  参考文献：
  名称：

  N-Silyloxaziridines: Synthesis and Use for Electrophilic Amination

  摘要：

  N-Silyloxaziridines were synthesized for the first time. Their tert-butyldiphenylsilyl (TBDPS) derivatives were stable reagents that were prepared on a multigram scale in three steps and in 44% overall yield from the corresponding benzylamines. They were mild electrophilic aminating reagents that reacted at room temperature with diversely substituted primary and secondary amines to produce N-monoalkyl or N,N-dialkyl benzaldehyde hydrazones in 44-87% yield.

  DOI：

  10.1021/jo302182t

文献信息

• One-pot synthesis of 5-sulfonamidopyrazole from terminal alkynes, sulfonyl azides and hydrozones
  作者：Yao Li、Deng Hong、Yuanxun Zhu、Ping Lu、Yanguang Wang

  DOI：10.1016/j.tet.2011.08.067

  日期：2011.10

  5-Sulfonamidopyrazoles were efficiently synthesized from terminal alkynes, sulfonyl azides and hydrozones. The sequential reaction involves a copper-catalyzed three-component reaction, a Lewis acid-catalyzed electrocyclic reaction and a dehydrogenation.

  从末端炔烃，磺酰基叠氮化物和氢zone有效地合成了5-磺酰胺基吡唑。顺序反应包括铜催化的三组分反应，路易斯酸催化的电环反应和脱氢。
• Stereospecific Copper(II)-Catalyzed Tandem Ring Opening/Oxidative Alkylation of Donor–Acceptor Cyclopropanes with Hydrazones: Synthesis of Tetrahydropyridazines
  作者：Manmath Mishra、Pinaki Bhusan De、Sourav Pradhan、Tharmalingam Punniyamurthy

  DOI：10.1021/acs.joc.9b01506

  日期：2019.9.6

  Aerobic copper(II)-catalyzed tandem ring opening and oxidative C–H alkylation of donor–acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89–98% enantiomeric excess)

  好氧铜（II）催化的串联环开环和供体-受体环丙烷与双芳基的氧化CH烷基化反应可制得四氢哒嗪，其中铜（II）既起路易斯酸的作用，又起氧化还原催化剂的作用。该反应具有立体特异性，旋光性环丙烷可以高光学纯度（过量89-98％对映异构体）进行反应。底物范围，官能团耐受性，铜（II）催化剂的双重作用以及使用空气作为氧化剂是重要的实用功能。带有3-溴芳基的产物可以高产率地与硼酸进行Pd催化的Suzuki偶联。
• The use of enaminones and enamines as effective synthons for MSA-catalyzed regioselective synthesis of 1,3,4-tri- and 1,3,4,5-tetrasubstituted pyrazoles
  作者：Liancheng Duan、Hui Zhou、Yucheng Gu、Ping Gong、Mingze Qin

  DOI：10.1039/c9nj03701b

  日期：——

  In the present work, an efficient regioselective synthesis of 1,3,4-tri- and 1,3,4,5-tetrasubstituted pyrazoles via a methanesulfonic acid (MSA)-catalyzed reaction of hydrazones with enaminones or enamines is reported. Mechanistically, the formation of the title compounds involves the [2+3] cycloaddition of hydrazones with enaminones or enamines followed by aromatization with acid and oxygen. This

  在本工作中，已报道了通过甲磺酸（MSA）催化的azo与烯胺酮或烯胺的反应有效地区域选择性合成1,3,4-三-和1,3,4,5-四取代的吡唑。从机理上讲，标题化合物的形成涉及与烯胺酮或烯胺的[2 + 3]环加成，然后用酸和氧进行芳构化。在温和条件下使用各种，烯胺酮和烯胺进行这种方便的方法具有良好的耐受性，从而可以以良好或极好的收率提供产品。与文献方法相比，该策略具有诸如可经济获得的材料，无金属催化，优异的区域选择性和高效率等优点。
• REGENERATION OF CARBONYL COMPOUNDS FROM OXIMES, PHENYLHYDRAZONES,<i>p</i>-NITROPHENYLHYDRAZONES, AND SEMICARBAZONES BY QUINOLINIUM DICHROMATE UNDER NONAQUEOUS CONDITIONS
  作者：Majid Mirmohammad Sadeghi、Iraj Mohammadpoor-Baltork、Mehdi Azarm、Mohammad Reza Mazidi

  DOI：10.1081/scc-100000536

  日期：2001.1

  Treatment of oximes, phenylhydrazones, p-nitrophenyl-hydrazones, and semicarbazones with quinolinium dichromate (QDC) affords the corresponding carbonyl compounds in high yields under mild conditions.

  用重铬酸喹啉 (QDC) 处理肟、苯腙、对硝基苯腙和缩氨基脲，在温和条件下以高产率得到相应的羰基化合物。
• Infrared irradiation assisted both the synthesis of ( Z)-(aminomethyl)(aryl)phenylhydrazones via the Mannich coupling reaction and their application to the palladium-catalyzed Heck reaction
  作者：Fernando Ortega-Jiménez、José Guillermo Penieres-Carrillo、Selene Lagunas-Rivera、José G. López-Cortés、Cecilio Álvarez-Toledano、M. Carmen Ortega-Alfaro

  DOI：10.1039/c5ra12715g

  日期：——

  The synthesis of arylhydrazones 1a–h assisted with infrared irradiation (IR) under solvent-free conditions is herein reported, and their catalytic action in the palladium-catalyzed and IR-assisted Heck coupling reaction are also evaluated.

  在无溶剂条件下，利用红外辐射（IR）辅助合成芳基腙1a–h的方法在此报告，并评估它们在钯催化和红外辐射辅助的Heck偶联反应中的催化作用。