3-ethoxy-4-hydroxybenzaldoxime | 34184-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-ethoxy-4-hydroxybenzaldoxime
• 英文别名: 3-ethoxy-4-hydroxy-benzaldehyde-oxime；3-Aethoxy-4-hydroxy-benzaldehyd-oxim；2-Ethoxy-4-(hydroxyiminomethyl)phenol
• CAS: 34184-93-5
• 化学式: C₉H₁₁NO₃
• mdl: MFCD01070633
• 分子量: 181.191
• InChiKey: AZAMLLOELYKGDG-UHFFFAOYSA-N

物化性质

• 沸点：
  323.8±32.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  3-ethoxy-4-hydroxybenzaldoxime 在 (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到3-乙氧基-4-羟基苯甲腈
  参考文献：
  名称：

  An unexpected involvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product in the promotion of the synthesis of nitriles from aldoximes: a mechanistic perception

  摘要：

  While attempting to synthesize nitriles from aldoximes using O-sulfonate esters of oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate], an unexpected involvement of oxyma cleaved product in promoting the synthesis of nitriles was observed. Such involvement of the oxyma cleaved product in the reaction mechanism, together with the usual anticipated pathway improved drastically the applicability of the method by reducing the time needed for the reaction to be completed over that of the sulfonyl chlorides. Other advantages of the present protocol are excellent yields in ambient and milder conditions. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.149
• 作为产物：
  描述：

  乙基香兰素 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 为溶剂， 反应 2.0h， 以24%的产率得到3-ethoxy-4-hydroxybenzaldoxime
  参考文献：
  名称：

  羟基或甲氧基取代的苯甲醛肟和苯甲醛-O-烷基肟作为酪氨酸酶抑制剂。

  摘要：

  合成了几种苯甲醛肟，苯甲醛-O-乙基肟和对乙酰氨基苯甲酸，并通过基于酪氨酸酶催化的L-DOPA氧化的分析，评估它们作为酪氨酸酶抑制剂。苯甲醛肟本身仅是一种弱抑制剂，而其衍生物在对位和间位具有一个或两个羟基或甲氧基部分则降低了酪氨酸酶的活性。苯乙酮肟和三取代的苯甲醛肟没有抑制活性。3,4-二羟基苯甲醛-O-乙基肟（0.3 +/- 0.1 micromol L（-1））的IC（50）与托酚酮（0.13 +/- 0.08 micromol L（-1））的幅度相同，一个迄今为止已知的最佳酪氨酸酶抑制剂之一。

  DOI：

  10.1016/s0968-0896(01)00084-0

文献信息

• Solvent Free, Microwave Assisted Conversion of Aldehydes into Nitriles and Oximes in the Presence of NH2OH·HCl and TiO2
  作者：Lucas Villas-Boas Hoelz、Biank Tomaz Gonçalves、José Celestino Barros、Joaquim Fernando Mendes da Silva

  DOI：10.3390/molecules15010094

  日期：——

  Aromatic aldehydes bearing electron-donating groups are easily converted into their respective nitriles using NH(2)OH.HCl and TiO(2) under microwave irradiation, while those bearing an electron-withdrawing group give the corresponding oximes.

  带有供电子基团的芳香醛很容易在微波照射下使用 NH(2)OH.HCl 和 TiO(2) 转化为各自的腈，而带有吸电子基团的芳香醛则产生相应的肟。
• Efficient hydrogenation of benzaldoximes and Schiff bases on ceramic high-porosity palladium catalysts
  作者：A. V. Ignatov、A. E. Varakutin、I. N. Solov’eva、I. B. Karmanova、I. A. Kozlov、M. N. Semenova、V. V. Semenov

  DOI：10.1007/s11172-018-2230-4

  日期：2018.8

  An efficient catalytic method for the synthesis of benzyl- and dibenzylamines by hydrogenating oximes and Schiffbases was developed on palladium supported high-porosity foamed ceramic block catalyst. The multiple regeneration ability of the foamed ceramic block catalyst can significantly decrease the Pd consumption as compared to the use of the conventional 10%Pd/C catalyst. Owing to a high hardness

  在钯负载的高孔隙率泡沫陶瓷块状催化剂上开发了一种通过肟和席夫碱加氢合成苄基和二苄胺的有效催化方法。与使用传统的10%Pd/C催化剂相比，泡沫陶瓷块状催化剂的多次再生能力可以显着降低Pd消耗。由于泡沫陶瓷催化剂的高硬度，反应混合物可以快速从反应器中去除，而无需使用过滤装置。反应产生的结构是具有生物活性的天然分子的片段。在海胆胚胎模型上揭示的二苄胺的抗增殖特性表明，这些化合物可以被认为是设计新抗癌药物的有前途的药物。
• Production of Oximes Directly from Sustainable Lignocellulose‐Derived Aldehydes and Ammonia over HTS‐1 Catalyst
  作者：Wanping Zheng、Shanshan Feng、Changwei Hu

  DOI：10.1002/cssc.202301364

  日期：2024.2.22

  Oxime chemicals are the building blocks of many anticancer drugs and widely used in industry and laboratory. A simple but robust hierarchically porous zeolite (HTS‐1) catalyst was prepared by hydrothermal methods and used for the preparation of vanillin oxime from vanillin in NH₃ ⋅ H₂O/DIO (v/v 1/10) system. The results of the catalyst characterization showed that the larger pore size and more framework Ti were conducive to promote the transformation of the substrates. The conversion of vanillin and the yield of vanillin oxime were both higher than 99 % under optimized reaction conditions. It was found that the reaction proceeded by oxidation of NH₃ to hydroxylamine (NH₂OH), and oximation of hydroxylamine with vanillin to obtain vanillin oxime, where the rate‐controlling step was the hydroxylamine formation, and the apparent activation energy was 26.22 kJ/mol. The corresponding oximation products could also be obtained by extending this method to other compounds derived from lignin. Furthermore, the catalytic system was used directly to the conversion of birch biomass to obtain oxime products such as vanillin oxime, syringaldehyde oxime, and furfural oxime etc. This work might give insights into the sustainable production of N‐containing high‐value products from lignocellulose.

  摘要肟类化学品是许多抗癌药物的基本成分，广泛应用于工业和实验室。采用水热法制备了一种简单而坚固的分层多孔沸石（HTS-1）催化剂，并将其用于在 NH3 ⋅ H2O/DIO (v/v 1/10) 体系中以香兰素为原料制备香兰素肟。催化剂表征结果表明，较大的孔径和较多的骨架 Ti 有利于促进底物的转化。在优化的反应条件下，香兰素的转化率和香兰素肟的产率均高于 99%。研究发现，反应是通过 NH3 氧化成羟胺（NH2OH），羟胺与香兰素氧化生成香兰素肟，其中控制速率的步骤是羟胺的形成，表观活化能为 26.22 kJ/mol。将此方法推广到木质素衍生的其他化合物中，也可获得相应的肟化产物。此外，该催化系统还被直接用于桦木生物质的转化，以获得肟产品，如香草醛肟、丁香醛肟、糠醛肟等。这项工作可能会为从木质纤维素中可持续地生产含氮高价值产品提供启示。
• (Z)-3,4,4,4-Tetrachlorobut-2-enoates of Certain Natural Alcohols, Phenols, and Oximes
  作者：E. A. Dikusar、V. I. Potkin、S. K. Petkevich、R. V. Kaberdin、N. G. Kozlov、A. V. Bazhanov、N. V. Kovganko

  DOI：10.1023/b:conc.0000039130.83796.88

  日期：2004.5

  Previously unknown (Z)-3,4,4,4-tetrachlorobut-2-enoateslb-20b were prepared in 77-88%yieldsby reaction in the presence of pyridine of 3,3,4,4,4-pentachlorobutanoic acid chloride with cetyl alcohol (1a), terpenols and terpenone oximes (2a-13a), sterols (14a and 15a), diosgenin (16a), and plant phenols and their oximes (17a-20a).
• Hirao, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1931, vol. 52, p. 26,29
  作者：Hirao

  DOI：——

  日期：——