4-乙酰氨基苯基醛肟 | 110853-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-乙酰氨基苯基醛肟
• 英文名称: (E)-N-[4-[hydroxyiminomethyl]phenyl]acetamide
• 英文别名: 4-Acetamidophenylaldoxime；4-acetylamino-benzaldehyde-oxime；Essigsaeure-(4-formohydroximoyl-anilid)；4-Acetylamino-benzaldehyd-oxim；4-Acetamino-benzaldehyd-oxim；4-Acetamino-benzaldoxim；N-{4-[(hydroxyimino)methyl]phenyl}acetamide；N-[4-[(E)-hydroxyiminomethyl]phenyl]acetamide
• CAS: 110853-54-8
• 化学式: C₉H₁₀N₂O₂
• mdl: MFCD00019962
• 分子量: 178.191
• InChiKey: SZGJLXKFWSTIKP-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-乙酰氨基苯基醛肟 在 N,N'-二环己基碳二亚胺 、 pyridinium chlorochromate 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 0.5h， 以60%的产率得到对乙酰氨基苯甲醛
  参考文献：
  名称：

  Bhat, Neelima Balkrishen; Bhaduri, A. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 1286 - 1287

  摘要：

  DOI：
• 作为产物：
  描述：

  对氨基苯甲醛 在 羟胺 、 sodium acetate 作用下， 生成 4-乙酰氨基苯基醛肟
  参考文献：
  名称：

  Gabriel; Herzberg, Chemische Berichte, 1883, vol. 16, p. 2000

  摘要：

  DOI：

文献信息

• Continuous Platform To Generate Nitroalkanes On-Demand (in Situ) Using Peracetic Acid-Mediated Oxidation in a PFA Pipes-in-Series Reactor
  作者：Sergey V. Tsukanov、Martin D. Johnson、Scott A. May、Stanley P. Kolis、Matthew H. Yates、Jeffrey N. Johnston

  DOI：10.1021/acs.oprd.8b00113

  日期：2018.8.17

  of peroxides and nitroalkanes. The subsequent continuous extraction generates a solution of purified nitroalkane, which can be directly used in the following enantioselective aza-Henry chemistry to furnish valuable chiral diamine precursors with high selectivity, thus completely avoiding isolation of the potentially unsafe low-molecular-weight nitroalkane intermediate. A continuous campaign (16 h) established

  氮杂-亨利反应的合成效用可因与使用过酸制备硝基烷烃底物和硝基烷烃本身有关的潜在危害而在规模上减小。作为响应，报道了连续和可扩展的化学平台，其使用肟与过氧乙酸的氧化和硝基链烷中间体在aza-Henry反应中的直接反应按需制备脂肪族硝基链烷。独特设计的串联管式活塞流管反应器解决了一系列工艺难题，包括过氧化物和硝基烷的稳定性和安全处理。随后的连续萃取生成纯化的硝基烷溶液，可将其直接用于以下对映选择性aza-Henry化学中，以高选择性提供有价值的手性二胺前体，因此，完全避免了可能不安全的低分子量硝基烷中间体的分离。连续运动（16小时）证明这些条件对于处理100克肟和提供1.4升硝基烷溶液有效。
• Ashley et al., Journal of the Chemical Society, 1942, p. 103,107
  作者：Ashley et al.

  DOI：——

  日期：——
• Exploring the Scope of the 29G12 Antibody Catalyzed 1,3-Dipolar Cycloaddition Reaction
  作者：Jonathan D. Toker、Martin R. Tremblay、Jari Yli-Kauhaluoma、Anita D. Wentworth、Bin Zhou、Paul Wentworth,、Kim D. Janda

  DOI：10.1021/jo050410b

  日期：2005.9.1

  29G12 is a murine monoclonal antibody programmed to catalyze the regio- and enantioselective 1,3-dipolar cycloaddition reaction between 4-acetamidobenzonitrile N-oxide la and N,N-dimethylacrylamide 2a (Toker, J. D.; Wentworth, P., Jr.; Hu, Y.; Houk, K. N.; Janda, K. D. J. Am. Chem. Soc. 2000, 122, 3244). Given the unique nature of 29G12 as a protein biocatalyst for this chemical reaction, we have investigated both the substrate specificity and mechanistic parameters of the 29G12-catalyzed process. These studies have shown that while 29G12 is specific for its dipole substrate la, the antibody is highly promiscuous with respect to the dipolarophiles it can process. 29G12 accepts a bulky hydrophobic dipolarophile cosubstrate, with rates of product formation up to 70-fold faster than with the original substrate 2a. In all cases, the respective isoxazoline products are produced with exquisite regio- and stereochemical control (78-98% ee). Comparison between the steady-state kinetic parameters from the 29G12-catalyzed reaction of la with the most efficient versus the original dipolarophile cosubstrate (2m and 2a, respectively), reveals that while the effective molarities (EM)s are almost identical (EM(2m) 26 M; EM(2a) 23 M), the affinity of 29G12 for the larger dipolarophile 2m is more than 1 order of magnitude higher than for 2a [K-m(2m) 0.44 +/- 0.04 mM; K-m(2a) 5.8 +/- 0.4 mM]. Furthermore, when 2m is the cosubstrate, the affinity of 29G12 for its dipole la is also greatly improved [K-m(1a) 0.82 +/- 0.1 mM compared to K-m(1a) 3.4 +/- 0.4 mM when 2a is the cosubstrate]. An analysis of the temperature dependence of the 29G12-catalyzed reaction between la and 2m reveals that catalysis is achieved via a decrease in enthalpy of activation (Delta Delta H-double dagger 4.4 kcal mol(-1)) and involves a large increase in the entropy of activation (Delta Delta S-double dagger 10.4 eu). The improved affinity of 29G12 for the nitrile oxide la in the presence of 2m, coupled with the increase in Delta Delta S-double dagger during the 29G12-catalyzed reaction between la and 2m supports the notion of a structural reorganization of the active site to facilitate this antibody-catalyzed reaction.
• CLXIII.—Symmetrical triad prototropic systems. Part VII. The analogy between symmetrical triad systems and aromatic side-chain reactivity, and the effect of p-substitution on mobility and equilibrium in the αγ-diphenylmethyleneazomethine system
  作者：Charles William Shoppee

  DOI：10.1039/jr9310001225

  日期：——
• Balsamo; Lapucci; Macchia, Il Farmaco, 1994, vol. 49, # 2, p. 77 - 82
  作者：Balsamo、Lapucci、Macchia、Martinelli、Nencetti、Rossello

  DOI：——

  日期：——