(E)-benzaldehyde O-(4-nitrobenzoyl)oxime

• 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)-benzaldehyde O-(4-nitrobenzoyl)oxime
• 英文别名: (E)-benzaldehyde O-4-nitrobenzoyl oxime；[(E)-benzylideneamino] 4-nitrobenzoate
• 化学式: C₁₄H₁₀N₂O₄
• 分子量: 270.244
• InChiKey: YBYQEOUMQIXFAD-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-benzaldehyde O-(4-nitrobenzoyl)oxime 生成 苯甲腈
  参考文献：
  名称：

  GRANT, R. D.;PINHEY, J. T.;RIZZARDO, E., AUSTRAL. J. CHEM., 1984, 37, N 6, 1217-1229

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1-(4'-nitrophenyl)-1-nitro-2-phenylethene 生成 (E)-benzaldehyde O-(4-nitrobenzoyl)oxime
  参考文献：
  名称：

  GRANT, R. D.;PINHEY, J. T.;RIZZARDO, E., AUSTRAL. J. CHEM., 1984, 37, N 6, 1217-1229

  摘要：

  DOI：

文献信息

• A Convenient Practical Synthesis of Alkyl and Aryl Oxime Esters
  作者：Bheemanakere Bettadaiah、S. Santosh Kumar、Nanjundaswamy Vijendra Kumar、Pullabhatla Srinivas

  DOI：10.1055/s-0034-1378350

  日期：——

  Abstract A facile access to the synthesis of alkyl and aryl oxime esters of ketoximes and aldoximes in high yields (90–97%) is reported. The reactions were performed using N-[3-(methylamino)propyl]-N′-ethylcarbodiimide hydrochloride (EDCI) reagent in the presence of 4-(dimethylamino)pyridine (DMAP) as a catalyst at room temperature. The isolation and purification of products is very simple and in cases

  摘要 据报道，以高产率（90-97％）可以轻松合成酮肟和醛肟的烷基和芳基肟酯。使用进行该反应ñ - [3-（甲基氨基）丙基] - ñ '-ethylcarbodiimide盐酸盐（EDCI）试剂中的4-存在（二甲基氨基）吡啶（DMAP）在室温下的催化剂。产物的分离和纯化非常简单，并且在产物为固体的情况下，可避免使用柱色谱法。 据报道，以高产率（90-97％）可以轻松合成酮肟和醛肟的烷基和芳基肟酯。使用进行该反应ñ - [3-（甲基氨基）丙基] - ñ '-ethylcarbodiimide盐酸盐（EDCI）试剂中的4-存在（二甲基氨基）吡啶（DMAP）在室温下的催化剂。产物的分离和纯化非常简单，并且在产物为固体的情况下，可避免使用柱色谱法。
• Sustainable Synthesis of Oximes, Hydrazones, and Thiosemicarbazones under Mild Organocatalyzed Reaction Conditions
  作者：Sara Morales、José Luis Aceña、José Luis García Ruano、M. Belén Cid

  DOI：10.1021/acs.joc.6b01912

  日期：2016.10.21

  thiosemicarbazones derived from aromatic and aliphatic aldehydes using equimolar amounts of reagents and green solvents. Experimental simplicity and excellent yields after a simple filtration are the main advantages of the method, being an alternative to those currently available especially for the acyl derivatives, which do not work under uncatalyzed conditions. Its application to the synthesis of acyloximes by

  吡咯烷很有效地催化，大概是通过亚胺基活化，使用等摩尔量的试剂和绿色溶剂，形成了芳香族和脂肪族醛衍生的酰基肟，酰基hydr和硫代半氨基甲酮。该方法的主要优点是实验简单，过滤简单后的优异收率，是目前可用于那些特别是酰基衍生物的替代方法，这些方法在未催化条件下不起作用。通过醛和酰基羟胺之间的直接缩合将其用于合成酰基肟的应用是空前的。
• Direct C−C Double Bond Cleavage of Alkenes Enabled by Highly Dispersed Cobalt Catalyst and Hydroxylamine
  作者：Wenxuan Xue、Yijie Jiang、Hongcheng Lu、Bo You、Xu Wang、Conghui Tang

  DOI：10.1002/anie.202314364

  日期：2023.12.21

  The utilization of a single‐atom catalyst to break C−C bonds merges the merits of homogeneous and heterogeneous catalysis and presents an intriguing pathway for obtaining high‐value‐added products. Herein, a mild, selective, and sustainable oxidative cleavage of alkene to form oxime ether or nitrile was achieved by using atomically dispersed cobalt catalyst and hydroxylamine. Diversified substrate patterns, including symmetrical and unsymmetrical alkenes, di‐ and tri‐substituted alkenes, and late‐stage functionalization of complex alkenes were demonstrated. The reaction was successfully scaled up and demonstrated good performance in recycling experiments. The hot filtration test, catalyst poisoning and radical scavenger experiment, time kinetics, and studies on the reaction intermediate collectively pointed to a radical mechanism with cobalt/acid/O₂ promoted C−C bond cleavage as the key step.

  摘要 利用单原子催化剂断裂 C-C 键融合了均相催化和异相催化的优点，为获得高附加值产品提供了一条有趣的途径。在此，利用原子分散的钴催化剂和羟胺实现了烯烃的温和、选择性和可持续氧化裂解，生成肟醚或腈。该反应展示了多种底物形态，包括对称和不对称烯烃、二取代和三取代烯烃，以及复杂烯烃的后期官能化。该反应已成功放大，并在循环实验中表现出良好的性能。热过滤试验、催化剂中毒和自由基清除剂实验、时间动力学以及对反应中间产物的研究共同表明了以钴/酸/O2 促进 C-C 键裂解为关键步骤的自由基机理。
• Elimination Reactions of (<i>E</i>)- and (<i>Z</i>)-Benzaldehyde <i>O</i>-Benzoyloximes. Transition State Differences for the Syn- and Anti-Eliminations Forming Nitriles
  作者：Bong Rae Cho、Hak Suk Chung、Nam Soon Cho

  DOI：10.1021/jo980264s

  日期：1998.7.1

  Elimination reactions of (E)- and (Z)-benzaldehyde O-benzoyloximes 1 and 2 with DBU in MeCN have been investigated kinetically. The reactions are second order and exhibit Substantial Values of Hammett rho and k(H)/k(D) values, and an E2 mechanism is evident. The rate of elimination from 2 is approximately 36000 fold faster than that from 1. For reactions of 1 with DBU in MeCN, k(H)/k(D) = 3.3 +/- 0.2, Hammett rho value of 2.19 +/- 0.05, beta(1g) = -0.49 +/- 0.02, Delta H-double dagger = 10.4 +/- 0.6 kcal/mol, and Delta S-double dagger = -34.3 +/- 2.6 eu have been determined. The corresponding values for 2 are k(H)/k(D) = 7.3 +/- 0.2, rho = 1.21 +/- 0.05, beta(1g) = -0.40 +/- 0.01, Delta H-double dagger = 6.8 +/- 0.5 kcal/mol, and Delta S-double dagger = -25.8 +/- 1.9 eu, respectively. The results indicate that the anti-eliminations from 2 proceed via more symmetrical transition states with smaller degrees of proton transfer and N-alpha-OC(O)Ar bond cleavage, less negative charge development at the beta-carbon, and a greater extent of triple bond formation than that for the syn-elimination.