(E)-2-(2'-nitrobenzylidene)cyclohexanone | 29202-80-0

• 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: (E)-2-(2'-nitrobenzylidene)cyclohexanone
• 英文别名: (E)-2-(2-nitrobenzylidene)cyclohexanone；2-o-Nitrobenzylidencyclohexanon；2-(2-Nitrobenzyliden)cyclohexanon-(1)；2-(2-Nitrobenzylidene)Cyclohexanone；(2E)-2-[(2-nitrophenyl)methylidene]cyclohexan-1-one
• CAS: 29202-80-0
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: MDRNBUVIUKNKMS-PKNBQFBNSA-N

物化性质

• 熔点：
  95-97 °C(Solv: methanol (67-56-1))
• 沸点：
  414.9±44.0 °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：

  (E)-2-(2'-nitrobenzylidene)cyclohexanone 在 盐酸 、 铁粉 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 12.0h， 生成 1,2,3,4-四氢吖啶
  参考文献：
  名称：

  蓝光促进的碳-碳双键异构化及其在喹啉合成中的应用

  摘要：

  据报道在没有任何光氧化还原催化剂的情况下，蓝光促进的碳-碳双键异构化。在简单的有氧条件下，它可以快速获得一系列喹啉，收率好至极好。该方案是直接，无催化剂且操作方便的。

  DOI：

  10.1039/c7ob00558j
• 作为产物：
  描述：

  2-[hydroxy-(2-nitrophenyl)methyl]cyclohexan-1-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以64%的产率得到(E)-2-(2'-nitrobenzylidene)cyclohexanone
  参考文献：
  名称：

  E,E-2-Benzylidene-6-(nitrobenzylidene)cyclohexanones: Syntheses, cytotoxicity and an examination of some of their electronic, steric, and hydrophobic properties

  摘要：

  Three series of structurally isomeric 2-benzylidene-6-(nitrobenzylidene) cyclohexanones 1-3 were prepared and evaluated against human Molt/C8 and CEM T-lymphocytes as well as murine L1210 cells. The IC50 values of the majority of compounds are less than 10 mu M and in some assays, the figures for 1d and 1e are submicromolar. Correlations were discerned between cytotoxic potencies and the atomic charges on one of the olefinic carbon atoms, the torsion angles between an aryl ring, and the adjacent unsaturated group as well as logP values. Three representative compounds were examined for their effect on respiration in rat liver mitochondria. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.029

文献信息

• 含硝基的姜黄素衍生物及其制备方法与应用
  申请人：温州医科大学

  公开号：CN104557558B

  公开（公告）日：2017-06-20

  本发明公开了一种式(I)姜黄素衍生物及其制备方法与应用，本发明提供一种新的姜黄素衍生物，且该衍生物具有抗炎活性，能够用做抗炎类药物或抗炎类药物组合物的有效成分。本发明还提供一种式(I)姜黄素衍生物的制备方法。本发明属于化学药物技术领域，稳定性优于姜黄素，且制备成本低，可实现性好。
• Process For Production of 2-Benzylphenol Compound
  申请人：Kawazoe Kentaro

  公开号：US20080194882A1

  公开（公告）日：2008-08-14

  A process for producing a 2-benzylphenol compound represented by the following formula (2): wherein, R 1 , R 2 , R 3 and R 4 may be the same or different and are each independently hydrogen atom, alkyl group or the like; and R 5 , R 6 , R 7 , R 8 and R 9 are the same or different and are each independently hydrogen atom, alkyl group or the like, the process including reacting, in the presence of a dehydrogenating agent, a benzylidenecyclohexanone compound represented by the following formula (1) wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 have the same definitions as given above).

  一种生产以下式子(2)所代表的2-苄基苯酚化合物的方法： 其中，R1、R2、R3和R4可能相同或不同，分别独立地为氢原子、烷基或类似物；而R5、R6、R7、R8和R9也可能相同或不同，分别独立地为氢原子、烷基或类似物。该方法包括在脱氢剂存在下反应以下式子(1)所代表的苄基环己酮化合物： 其中，R1、R2、R3、R4、R5、R6、R7、R8和R9的定义与上述相同。
• METHOD FOR PRODUCING 2-BENZYLPHENOL COMPOUND
  申请人：IHARA CHEMICAL INDUSTRY CO., LTD.

  公开号：EP1810957A1

  公开（公告）日：2007-07-25

  [Task] Provide a process for producing a 2-benzylphenol compound easily, efficiently and selectively. [Means for Achievement] A process for producing a 2-benzylphenol compound represented by the following general formula (2) (in the formula, R1, R2, R3 and R4 may be the same or different and are each independently hydrogen atom, alkyl group or the like; and R5, R6, R7, R8 and R9 may be the same or different and are each independently hydrogen atom, alkyl group or the like), characterized by reacting, in the presence of a dehydrogenating agent, a benzylidenecyclohexanone compound represented by the following general formula (1) (in the formula, R1, R2, R3, R4, R5, R6, R7, R8 and R9 have the same definitions as given above). [Effect] A 2-benzylphenol compound substantially free from isomers can be produced from a benzylidenecyclohexanone compound (an easily obtainable raw material) selectively, efficiently and in a simple operation, under mild conditions without using any special reactor.

  任务 提供一种简便、高效、选择性地生产 2-苄基苯酚化合物的工艺。 [实现途径］ 一种由以下通式（2）表示的 2-苄基苯酚化合物的生产工艺 (式中，R1、R2、R3 和 R4 可以相同或不同，且各自独立地为氢原子、烷基或类似基团；R5、R6、R7、R8 和 R9 可以相同或不同，且各自独立地为氢原子、烷基或类似基团），其特征在于，在脱氢剂存在下，由下式通式（1）表示的亚苄基环己酮化合物发生反应 (式中，R1、R2、R3、R4、R5、R6、R7、R8 和 R9 的定义与上式相同）。 效果 在温和的条件下，无需使用任何特殊的反应器，就可以通过简单的操作，从亚苄基环己酮化合物（一种容易获得的原料）中选择性地、高效地生产出基本上不含异构体的 2-苄基苯酚化合物。
• Asymmetrical 2,6-bis(benzylidene)cyclohexanones: Synthesis, cytotoxic activity and QSAR study
  作者：Maryam Nakhjiri、Maliheh Safavi、Eskandar Alipour、Saeed Emami、Amir Farzin Atash、Mona Jafari-Zavareh、Sussan K. Ardestani、Mehdi Khoshneviszadeh、Alireza Foroumadi、Abbas Shafiee

  DOI：10.1016/j.ejmech.2012.01.045

  日期：2012.4

  In order to develop novel anti-cancer agents, a series of asymmetrical 2,6-bis (benzylidene)cyclohexanone derivatives containing nitrobenzylidene moiety were synthesized and their cytotoxic activity were determined in vitro against MDA-MB 231, MCF-7 and SK-N-MC cell lines using MTT assay. Among the tested compounds, the highest activity against MDA-MB 231 cells was achieved by 2-(3-bromo-5-methoxy-4-propoxybenzylidene)-6-(2-nitrobenzylidene)cyclohexanone (compound 5d). Whereas, compound 5j (the 3-nitro analog of compound 5d) was the most potent compound against MCF-7 and SK-N-MC cell lines. The results indicated that the cytotoxic activity profile against different tumor cells can be optimized by desired 4-alkoxy-3-bromo-5-methoxybenzylidene scaffold. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis of Quinolines, 2-Quinolones, Phenanthridines, and 6(5<i>H</i>)-Phenanthridinones via Palladium[0]-Mediated Ullmann Cross-Coupling of 1-Bromo-2-nitroarenes with β-Halo-enals, -enones, or -esters
  作者：Martin G. Banwell、David W. Lupton、Xinghua Ma、Jens Renner、Magne O. Sydnes

  DOI：10.1021/ol0490375

  日期：2004.8.1

  Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of beta-halo-enals, -enones, or -esters readily affords the corresponding beta-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with dihydrogen in the presence of Pd on C or with TiCl3 in aqueous acetone.