m-hydroxyacetophenone oxime

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: m-hydroxyacetophenone oxime
• 英文别名: 1-(3-Hydroxyphenyl)ethanone oxime；3-(N-hydroxy-C-methylcarbonimidoyl)phenol
• 化学式: C₈H₉NO₂
• 分子量: 151.165
• InChiKey: WPEOEYHUTFZJKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  m-hydroxyacetophenone oxime 在 ammonium hydroxide 、 氢气 、 镍 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 3-(1-氨基乙基)苯酚
  参考文献：
  名称：

  Identification and SAR of squarate inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

  摘要：

  A novel series of inhibitors for mitogen activated protein kinase-activated protein kinase 2 (MK-2) are reported. These squarate based inhibitors were identified via a high-throughput screen. An MK2 co-structure with the starting ligand was obtained and a structure based approach was followed to optimize potency and selectivity.

  DOI：

  10.1016/j.bmc.2009.03.041
• 作为产物：
  描述：

  3-羟基苯乙酮 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以76%的产率得到m-hydroxyacetophenone oxime
  参考文献：
  名称：

  通过溶剂辅助和稳健的机械化学途径 合成酮肟†

  摘要：

  通过简单的研钵-研杵研磨方法，已经为多种酮类建立了一种通用且稳健的机械化学路线，以实现酮-肟的转化。还研究了在这些条件下醛相对于酮的相对反应性，以及对反应性与电子取代基效应之间可能的联系的研究。

  DOI：

  10.1039/c3ra40585k

文献信息

• Synthesis of ketoximes via a solvent-assisted and robust mechanochemical pathway
  作者：Christer B. Aakeröy、Abhijeet S. Sinha

  DOI：10.1039/c3ra40585k

  日期：——

  mechanochemical route to ketone–oxime conversions has been established for a broad range of ketones via a simple mortar–pestle grinding method. The relative reactivity of aldehydes vs. ketones under these conditions has also been explored, along with an examination of the possible connection between reactivity and electronic substituent effects.

  通过简单的研钵-研杵研磨方法，已经为多种酮类建立了一种通用且稳健的机械化学路线，以实现酮-肟的转化。还研究了在这些条件下醛相对于酮的相对反应性，以及对反应性与电子取代基效应之间可能的联系的研究。
• Cobalt(III)-Catalyzed Dehydrative [4+2] Annulation of Oxime with Alkyne by CH and NOH Activation
  作者：Malay Sen、Deepti Kalsi、Basker Sundararaju

  DOI：10.1002/chem.201503643

  日期：2015.10.26

  Efficient, scalable cobalt‐catalyzed redox‐neutral [4+2] annulation of readily available oximes and alkyne is reported. The developed synthetic methodology is widely applicable and tolerates various functional groups including heterocycles. A stable Cp*CoIII neutral complex is employed as the catalyst for this redox‐neutral [4+2] annulation reaction, which progresses smoothly by way of a reversible

  据报道，高效，可扩展的钴催化的氧化还原中性[4 + 2]环化易于获得的肟和炔烃。所开发的合成方法学广泛适用，并能耐受包括杂环在内的各种官能团。稳定的Cp * Co III中性络合物用作该氧化还原-中性[4 + 2]环化反应的催化剂，该反应通过可逆的环金属化反应顺利进行，而无需任何外部氧化剂，仅产生水作为副产物。
• Beckmann rearrangement of oximes using pivaloyl chloride/DMF complex
  作者：Srinivasa Reddy Narahari、Buchi Reddy Reguri、K. Mukkanti

  DOI：10.1016/j.tetlet.2011.07.045

  日期：2011.9

  A new complex of pivaloyl chloride and DMF was found to be very effective for converting ketoximes into their corresponding amides or lactams with excellent conversion via the Beckmann rearrangement. This method offers significant advantages such as efficiency and mild reaction conditions with shorter reaction time.

  发现新的新戊酰氯和DMF的复合物通过贝克曼重排能以优异的转化率将酮肟转化为其相应的酰胺或内酰胺非常有效。该方法具有显着的优势，例如效率高，反应条件温和，反应时间短。
• Beckmann Rearrangement of Oximes Using Doped Silica Gel Complex
  作者：Y. Umanadh、N. Srinivasa Reddy、Khagga Mukkanti、G. Omprakash

  DOI：10.14233/ajchem.2015.17170

  日期：——

  A new complex of perchloric acid absorbed on silica gel (doped silica gel) and dichloromethane was found to be very effective for converting ketoximes into their corresponding amides or lactams with excellent conversion via the Beckmann rearrangement. This method offers significant advantages such as efficiency and mild reaction conditions with shorter reaction time.

  在硅胶上吸附的高氯酸新复合物（掺杂硅胶）与二氯甲烷的组合被发现对于通过贝克曼重排将酮肟高效转化为相应的酰胺或内酰胺具有极佳的转化效果。该方法具有显著优势，如高效性和温和的反应条件，反应时间更短。
• Natural organic acids promoted Beckmann rearrangement: Green and expeditious synthesis of amides under solvent-free conditions
  作者：Sandeep Rohokale、Santosh Kote、Santosh Deshmukh、Shankar Thopate

  DOI：10.2478/s11696-013-0481-y

  日期：2014.1.1

  Naturally occurring organic acids are reported to be highly efficient promoters of the Beckmann rearrangement. Citric, oxalic, tartaric, malic, succinic, malonic, and fumaric acids efficiently promote the Beckmann rearrangement under solvent-free conditions and thermal and microwave irradiation. Tartaric acid was found to be the best promoter of the Beckmann rearrangement under conventional conditions as well as under microwave irradiation. Compared with conventional heating, microwave irradiation provides higher reaction rate and slightly higher yields.

  据报道，天然存在的有机酸被认为是Beckmann重排反应的高效促进剂。柠檬酸、草酸、酒石酸、苹果酸、琥珀酸、丙二酸和富马酸在无溶剂条件下以及热和微波辐射下有效促进了Beckmann重排反应。在常规条件和微波辐射下，酒石酸被发现是Beckmann重排反应的最佳促进剂。与常规加热相比，微波辐射提供更高的反应速率和略微更高的产率。