2-(4-nitrobenzylidene)cyclohexanone | 22114-45-0

• 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: 2-(4-nitrobenzylidene)cyclohexanone
• 英文别名: 2-(4-nitrobenzylidene)cyclohexan-1-one；2-(4-Nitrobenzyliden)cyclohexanon-(1)；2-(p-Nitrobenzal)-cyclohexanone；2-[(4-nitrophenyl)methylidene]cyclohexan-1-one
• CAS: 22114-45-0
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: WKEXENOSHSPMMW-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C(Solv: ligroine (8032-32-4))
• 沸点：
  385.1±31.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-nitrobenzylidene)cyclohexanone 、 2,3,4-三甲氧基苯甲醛 在 盐酸 作用下， 以 乙醚 、 氯仿 为溶剂， 以72%的产率得到6-(4-nitrobenzylidene)-2-(2,3,4-trimethoxybenzylidene)cyclohexanone
  参考文献：
  名称：

  Cytotoxic 2-benzylidene-6-(nitrobenzylidene)cyclohexanones which display substantially greater toxicity for neoplasms than non-malignant cells

  摘要：

  Various 2-benzylidene-6-(nitrobenzylidene)cyclohexanones were prepared as candidate cytotoxins in which the nitro group was located in the ortho, meta and para positions leading to series 1-3, respectively. The CC50 values towards human HSC-2 and HSC-4 oral squamous cell carcinomas as well as human HL-60 promyelocytic leukemic cells are in the low micromolar range in general. On the other hand, most of the compounds afforded clear evidence of being far less toxic towards human HGF gingival fibroblasts, HPC pulp cells and HPLF periodontal ligament. broblasts which are non-malignant cells. Selectivity index (SI) figures were generated which are the ratios of the average CC50 values towards normal cells and the CC50 figure towards a malignant cell line. Huge SI values were obtained for many of the compounds. In particular 1c, 2f, 3c and 3g which have average SI values of >76, >38, 124 and 341, respectively, are clearly lead molecules affording direction for amplification of this area of study. A lead compound 1c caused internucleosomal DNA fragmentation and activation of caspase-3 in HL-60 cells but not in HSC-2 carcinomas. In a short-term toxicity study, doses up to and including 300 mg/kg of the majority of the compounds prepared in this study did not cause any mortalities to mice. Some guidelines for development of these tumor-selective cytotoxins are presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.069
• 作为产物：
  描述：

  2-[hydroxy(4-nitrophenyl)methyl]cyclohexan-1-one 在 草酸 作用下， 生成 2-(4-nitrobenzylidene)cyclohexanone
  参考文献：
  名称：

  Vieweg; Wagner, Pharmazie, 1980, vol. 34, # 12, p. 785 - 788

  摘要：

  DOI：

文献信息

• An environmentally friendly Mukaiyama aldol reaction catalyzed by a strong Brønsted acid in solvent-free conditions
  作者：Margherita Barbero、Stefano Bazzi、Silvano Cadamuro、Stefano Dughera、Claudio Magistris、Alessandra Smarra、Paolo Venturello

  DOI：10.1039/c0ob00837k

  日期：——

  o-Benzenedisulfonimide, a new strong bench-stable Brønsted acid, has been shown to efficiently catalyze the Mukaiyama aldol reaction of aldehydes or dimethyl acetals with silyl enol ethers under mild solvent-free reaction conditions.

  o-苯二磺酰亚胺是一种新型强稳定的Brønsted酸，已被证明可在温和无溶剂的反应条件下高效催化醛或二甲基缩醛与烯醇硅醚的Mukaiyama羟醛反应。
• Functionalized CoFe₂O₄/lamellar mesopore silica anchored to melamine nanocomposite as a novel catalyst for synthesis of 4<i>H</i>‐chromenes under mild conditions
  作者：Somaye Mohammadi、Hossein Naeimi

  DOI：10.1002/aoc.5630

  日期：2020.6

  cyclohexanone, benzaldehyde and malononitrile for the synthesis of 4H‐chromenes by using CoFe2O4/lamellar mesopore silica anchored to melamine as a magnetic nanocatalyst. This nanocatalyst was prepared in several steps and discriminated by XRD, FT‐IR, SEM, VSM, TGA and BET techniques. The catalyst has a large active base site that has functionalized in both the surface and the pore of nanostructure. The

  在这项研究中，它展示了一种有效的方法，该方法通过使用锚定在三聚氰胺上的CoFe 2 O 4 /层状中孔二氧化硅作为磁性纳米催化剂，使环己酮，苯甲醛和丙二腈单锅反应合成4H-色烯。该纳米催化剂分几个步骤制备，并通过XRD，FT-IR，SEM，VSM，TGA和BET技术加以区分。该催化剂具有较大的活性碱位，该活性碱位在纳米结构的表面和孔中均已官能化。磁性纳米催化剂的优点是易于获得，多相纳米催化剂，易于加工和可重复使用。在CoFe 2 O 4的存在下合成了4H-色烯的各种衍生物/薄片中孔二氧化硅/三聚氰胺磁性纳米催化剂，具有优异的收率和合适的时间。产物通过熔点，FT-IR，1 H NMR，13 C NMR和CHN技术鉴定。
• Metal‐ and Solvent‐Free Transesterification and Aldol Condensation Reactions by a Homogenous Recyclable Basic Ionic Liquid Based on the 1,3,5‐Triazine Framework
  作者：Yanqiu Hu、Mingqi Ren、Milad Kazemnejadi

  DOI：10.1002/open.202100091

  日期：2021.8

  A new recyclable basic ionic liquid was introduced as an efficient catalyst for aldol condensation and transesterification reactions under environmentally friendly conditions. The catalyst was prepared based on methyl imidazolium moieties bearing hydroxide counter anions via the Hofmann elimination on a 1,3,5-triazine framework. The ionic liquid with two functionalities including anion stabilizer and

  引入了一种新型可回收碱性离子液体，作为环保条件下羟醛缩合和酯交换反应的有效催化剂。该催化剂基于带有氢氧根抗衡阴离子的甲基咪唑鎓部分，通过1,3,5-三嗪骨架上的霍夫曼消除反应制备。该离子液体具有阴离子稳定剂和高碱度两种功能，可用作羟醛缩合以及多种苯甲酸烷基酯酯交换反应的有效催化剂。所有反应均在没有任何外部试剂、助催化剂或溶剂的情况下进行，符合环境保护。对酯交换反应进行动力学同位素效应（KIE），以阐明其机理和速率决定步骤（RDS）。值得注意的是，均相催化剂可以从反应混合物中回收，并在多次连续运行中重复使用，碱度和转化率下降不显着。
• Modified calcium oxide as stable solid base catalyst for Aldol condensation reaction
  作者：YING TANG、JINGFANG XU、XUEFAN GU

  DOI：10.1007/s12039-013-0362-5

  日期：2013.3

  A highly efficient and stable solid-base catalyst for Aldol condensation was prepared by modifying commercial CaO with benzyl bromide in a simple way. It was found that modified CaO can effectively catalyse the Aldol condensation of cyclohexanone and benzaldehyde, as well as various benzaldehydes, to produce 2-benzylidenecyclohexanone with a good selectivity and high yield. Higher yield of 95.8% was obtained over modified CaO after 3 h, which is short compared with the yield of 92.1% after 12 h over commercial CaO. The influence of several reaction parameters, such as temperature, catalyst loading, was investigated. The humidity test over modified CaO reveals that the basic centres of modified CaO are stable for CO2 and moisture. From the results of Fourier transform-infrared (FT-IR) and Thermogravity analysis (TG) characterization, the modifier was bonded on surface of CaO chemically and almost no Ca(OH)2 formed during the modification process. The type of aldehyde has great influence on the yield of aldol condensation.

  一种高效稳定的固体碱催化剂用于阿尔多尔缩合反应，通过简单地用溴化苄修饰商业氢氧化钙（CaO）制备而成。研究发现，改性后的CaO能够有效催化环己酮与苯甲醛及各种苯甲醛的阿尔多尔缩合，生成2-苄基环己酮，具有良好的选择性和高产率。在3小时内，改性CaO的产率达到95.8%，相比之下，商业CaO在12小时后的产率仅为92.1%。还研究了温度、催化剂负载等多种反应参数的影响。对改性CaO的湿度测试表明，其基本中心对二氧化碳和水分是稳定的。通过傅里叶变换红外光谱（FT-IR）和热重分析（TG）表征的结果显示，修饰剂与CaO表面发生了化学结合，并且在修饰过程中几乎没有形成Ca(OH)2。醛的种类对阿尔多尔缩合的产率有很大影响。
• Synthesis of 1 <i>H</i> ‐isochromenes, 4 <i>H</i> ‐chromenes, and ortho‐aminocarbonitrile tetrahydronaphthalenes from the same reactants by using metal‐free catalyst
  作者：Hossein Naeimi、Somaye Mohammadi

  DOI：10.1002/jhet.3742

  日期：2020.1

  A facile and rapid multicomponent synthesis of pharmaceutically diverse 1H‐isochromenes, 4H‐chromenes, and ortho‐aminocarbonitrile tetrahydronaphthalenes has been developed from benzaldehyde, malononitrile, and cyclohexanone. Three different methods from the same reactants, solvent, temperature, and catalyst lead to three products with excellent yields. All the reactions were followed with the Michael

  从苯甲醛，丙二腈和环己酮开发了一种可快速合成药物的1 H-异色烯，4 H-色烯和邻氨基甲腈四氢萘的简便方法。使用相同的反应物，溶剂，温度和催化剂的三种不同方法可得到三种具有优异收率的产品。所有反应均伴随迈克尔加成和环化。在这项研究中，吗啉被用作不含金属的活性碱催化剂，可提高产物的收率并缩短反应时间。