3-Methyl-4-(4-nitrobenzylidene) isoxazol-5(4H)-one | 61588-02-1

• 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: 3-Methyl-4-(4-nitrobenzylidene) isoxazol-5(4H)-one
• 英文别名: 5(4H)-Isoxazolone, 3-methyl-4-[(4-nitrophenyl)methylene]-, (Z)-；3-methyl-4-[(4-nitrophenyl)methylidene]-1,2-oxazol-5-one
• CAS: 61588-02-1
• 化学式: C₁₁H₈N₂O₄
• 分子量: 232.196
• InChiKey: BLHMUVYAYXTPCU-UHFFFAOYSA-N

物化性质

• 沸点：
  350.2±52.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  3-Methyl-4-(4-nitrobenzylidene) isoxazol-5(4H)-one 以1.9 g的产率得到1-乙炔基-4-硝基苯
  参考文献：
  名称：

  降固闪蒸真空热解：芳基乙炔的有效制备

  摘要：

  自动化的降落固体闪蒸真空热解可以从醛前体制备的4-芳基亚甲基-5（4 H）-异恶唑酮衍生物快速高效地合成各种芳基乙炔。乙炔很容易以克数获得。

  DOI：

  10.1002/anie.201412431
• 作为产物：
  描述：

  bis(3-methylisoxazol-5(2H)-on-4-yl)-4'-nitrophenylmethane 反应 4.0h， 生成 3-Methyl-4-(4-nitrobenzylidene) isoxazol-5(4H)-one
  参考文献：
  名称：

  降固闪蒸真空热解：芳基乙炔的有效制备

  摘要：

  自动化的降落固体闪蒸真空热解可以从醛前体制备的4-芳基亚甲基-5（4 H）-异恶唑酮衍生物快速高效地合成各种芳基乙炔。乙炔很容易以克数获得。

  DOI：

  10.1002/anie.201412431

文献信息

• Fruit Extract of Averrhoa bilimbi: A Green Neoteric Micellar Medium for Isoxazole and Biginelli-Like Synthesis
  作者：Bhagyashree M. Patil、Sachinkumar K. Shinde、Ashutosh A. Jagdale、Swati D. Jadhav、Suresh S. Patil

  DOI：10.1007/s11164-021-04539-y

  日期：2021.10

  A transition metal/ligand/additive/promoter-free synthesis of 3-methyl-4-arylmethylene-isoxazol-5(4H)-ones and the Biginelli-like synthesis is carried out in a natural acidic medium of Averrhoa bilimbi extract (ABE) with cleaner and facile approach smentioned here. The isoxazol-5(4H)-ones and 11-acetyl-2-methyl-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]-oxadiaazocin-4(3H)-ones are synthesized, respectively, under aerobic conditions at room temperature and at reflux temperature of ethanol. This eco-friendly and economically cheap, non-toxic acidic catalytic media is obtained from the renewable resource, and its dynamic phase is confirmed by the optical microscopy, DLS technique, and with critical micelle concentration (c.m.c.) measurements. The notable advantages are excellent yields of the obtained products, versatility in handling substrates, reuse of the catalyst, use of no hazardous organic solvents, and minimization of waste or side products. So, the reported procedure is simple, evergreen, and a sound alternative to the existing protocols for isoxazol-5(4H)-one synthesis and for Biginelli-like synthesis as well.

  一种无过渡金属/配体/添加剂/促进剂的3-甲基-4-芳基亚甲基异噁唑-5(4H)-酮的合成以及类似Biginelli合成在Averrhoa bilimbi提取物（ABE）的天然酸性介质中进行，采用更清洁和更简便的方法。异噁唑-5(4H)-酮和11-乙酰基-2-甲基-5,6-二氢-2H-2,6-亚甲基苯并[g][1,3,5]-噁二唑嗪-4(3H)-酮分别在室温和乙醇回流温度下在有氧条件下合成。该生态友好、经济廉价、无毒的酸性催化介质来源于可再生资源，其动态相通过光学显微镜、动态光散射（DLS）技术和临界胶束浓度（c.m.c.）测量得到确认。显著的优点包括所获得产品的优异产率、底物处理的多样性、催化剂的重复使用、不使用有害有机溶剂以及废物或副产品的最小化。因此，报道的程序简单、环保，并且是现有异噁唑-5(4H)-酮合成和类似Biginelli合成的可靠替代方案。
• One-pot three-component synthesis of isoxazole using ZSM-5 as a heterogeneous catalyst
  作者：Navnath T. Hatvate、Shrikant M. Ghodse

  DOI：10.1080/00397911.2020.1815786

  日期：2020.12.1

  route for the synthesis of isoxazole derivatives has been developed using ZSM-5 as a heterogeneous catalyst. The reaction was carried out under a solvent-free condition to afford the desired products in good yields. A variety of functional groups was tolerated under the reaction conditions employed. Moreover, the heterogeneous catalyst (ZSM-5) was recovered and reused several times without significant

  摘要 以ZSM-5为多相催化剂，开发了一种温和、方便的合成异恶唑衍生物的路线。该反应在无溶剂条件下进行，以良好的收率得到所需产物。在所采用的反应条件下可以容忍多种官能团。此外，多相催化剂（ZSM-5）被回收并重复使用多次，而其催化活性没有显着损失。图形概要
• Green synthesis of 3,4‐disubstituted isoxazol‐5(4 <i>H</i> )‐ones using ZnO@Fe ₃ O ₄ core–shell nanocatalyst in water
  作者：M. Shanshak、Srinivasa Budagumpi、Jan Grzegorz Małecki、Rangappa S. Keri

  DOI：10.1002/aoc.5544

  日期：2020.4

  for the synthesis of isoxazol‐5(4H)‐one derivatives has been developed using a ZnO@Fe3O4 core–shell nanocatalytic system. The one‐pot, multicomponent reaction of an aromatic/heterocyclic aldehyde, hydroxylamine hydrochloride and ethyl acetoacetate under aqueous conditions at slightly elevated temperature resulted in the formation of title compounds in extremely good yields. The present new protocol

  已经开发了使用ZnO @ Fe 3 O 4合成异恶唑5（4 H）-one衍生物的有效且环保的方法核-壳纳米催化系统。芳族/杂环醛，盐酸羟胺和乙酰乙酸乙酯的单锅多组分反应在水性条件下在略微升高的温度下以极高的收率形成标题化合物。当前的新方案对环境友好，因为它提供了一些有趣的有前途的功能，如安全性，原子效率，低成本，温和的条件，废物最少，催化剂可回收性，水为溶剂，易于加工并具有出色的官能团耐受性结构上不同的异恶唑衍生物的合成。所有产品均通过光谱和分析方法表征。用单晶X射线衍射法研究了代表性的标题衍生物的结构。
• Boric acid-catalyzed multi-component reaction for efficient synthesis of 4H-isoxazol-5-ones in aqueous medium
  作者：Hamzeh Kiyani、Fatemeh Ghorbani

  DOI：10.1007/s11164-013-1411-x

  日期：2015.5

  one-pot three-component reaction of aryl aldehydes with hydroxylamine hydrochloride and ethyl 3-oxobutanoate/ethyl 4-chloro-3-oxobutanoate/ethyl 3-oxo-3-phenylpropanoate in the presence of boric acid, H3BO3, in water leads to 4H-isoxazol-5(4H)-ones in high yields. The merits of this method are efficiency, simplicity, clean, green, easy work-up, high yields, and shorter reaction times.

  芳基醛与盐酸羟胺和乙基3-氧代丁酸乙酯/乙酸乙酯4-氯-3-氧代丁酸乙酯/ 3-氧代-3-苯基丙在硼酸的存在下，一锅煮三组分反应，H 3 BO 3，在水导致高产率的4 H -isoxazol-5（4 H）-ones。该方法的优点是高效，简单，清洁，绿色，易于后处理，高收率和较短的反应时间。
• Green synthesis of 3-methyl-4-(hetero)aryl methylene isoxazole-5(4<i>H</i>)-ones using WEOFPA/glycerol: evaluation of anticancer and electrochemical behaviour properties
  作者：Krishnappa B. Badiger、Santosh Y. Khatavi、Kantharaju Kamanna

  DOI：10.1039/d2md00191h

  日期：——

  We demonstrate the MCRs of hydroxylamine hydrochloride and ethyl acetoacetate with various substituted aromatic and heteroaromatic aldehydes using an agro-waste-based solvent medium as a catalyst. The products were then screened for their anticancer activity.

  我们展示了利用农产废料溶剂介质作为催化剂，将盐酸羟胺和乙酰乙酸乙酯与各种取代的芳香族和杂芳香族醛进行 MCR 反应的过程。然后对产物进行了抗癌活性筛选。