2,6-bis(2-nitrobenzylidene)cyclohexanone | 10329-06-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,6-bis(2-nitrobenzylidene)cyclohexanone
• 英文别名: 2,6-BIs(o-nitrobenzyliden)cyclohexanon；2,6-bis[(E)-2-nitrobenzylidene]cyclohexanone；(2E,6E)-2,6-bis[(2-nitrophenyl)methylidene]cyclohexan-1-one
• CAS: 10329-06-3
• 化学式: C₂₀H₁₆N₂O₅
• 分子量: 364.357
• InChiKey: AHVDLCOSRDSNPH-UNZYHPAISA-N

物化性质

• 熔点：
  160-162 °C
• 沸点：
  609.0±55.0 °C(Predicted)
• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis(2-nitrobenzylidene)cyclohexanone 、 氯化亚锡 、 盐酸 以69%的产率得到
  参考文献：
  名称：

  KONSTANTINOVA, A. V.;MIXALINA, T. V.;FOKIN, E. P., IZV. CO AN CCCP. XIM. H,(1989) N, S. 57-61

  摘要：

  DOI：
• 作为产物：
  描述：

  环己酮 、 邻硝基苯甲醛 以 neat (no solvent) 为溶剂， 反应 0.42h， 以92%的产率得到2,6-bis(2-nitrobenzylidene)cyclohexanone
  参考文献：
  名称：

  由可重复使用的负载酸性离子液体有效催化的酮与芳香醛的无溶剂选择性交叉羟醛缩合

  摘要：

  摘要 一种新制备的由二氧化硅负载的酸性离子液体1-(4-磺酸)丁基硫酸氢吡啶组成的催化剂用于在无溶剂条件下催化酮与芳香醛的交叉羟醛缩合反应。高活性和选择性的催化剂在没有发生任何自缩合反应的情况下提供了良好到极好的所需交叉羟醛产物的产率。反应时间短，程序和后处理简单，不需要挥发性或危险的有机溶剂。此外，催化剂可以重复使用至少四次，活性仅略有降低。

  DOI：

  10.1016/s1872-2067(11)60470-1

文献信息

• Solvent-Free Selective Cross-Aldol Condensation of Ketones with Aromatic Aldehydes Efficiently Catalyzed by a Reusable Supported Acidic Ionic Liquid
  作者：Abolghasem DAVOODNIA、Ghazaleh YASSAGHI

  DOI：10.1016/s1872-2067(11)60470-1

  日期：2012.11

  Abstract A newly prepared catalyst consisting of acidic ionic liquid 1-(4-sulfonic acid) butylpyridinium hydrogen sulfate supported on silica was used to catalyze the cross-aldol condensation of ketones with aromatic aldehydes under solvent-free conditions. The highly active and selective catalyst gave good to excellent yields of the desired cross-aldol products without the occurrence of any self-condensation

  摘要 一种新制备的由二氧化硅负载的酸性离子液体1-(4-磺酸)丁基硫酸氢吡啶组成的催化剂用于在无溶剂条件下催化酮与芳香醛的交叉羟醛缩合反应。高活性和选择性的催化剂在没有发生任何自缩合反应的情况下提供了良好到极好的所需交叉羟醛产物的产率。反应时间短，程序和后处理简单，不需要挥发性或危险的有机溶剂。此外，催化剂可以重复使用至少四次，活性仅略有降低。
• Novel Synthesis and Crystal Structures of Two α, α′-bis-Substituted Benzylidene Cyclohexanones: 2,6-Bis-2-nitro(benzylidene)cyclohexanone and 2,6-Bis-4-methyl(benzylidene)cyclohexanone
  作者：Ali Amoozadeh、Salman Rahmani、Grzegorz Dutkiewicz、Mehdi Salehi、Firouzeh Nemati、Maciej Kubicki

  DOI：10.1007/s10870-011-0094-7

  日期：2011.9

  Two α,α′-bis-substituted benzylidene cycloalkanones have been synthesized in presence of SnCl4 and their crystal structures have been determined by means of X-ray diffraction. The bis(para-methyl) derivative, 2,6-bis-4-methyl(benzylidene)cyclohexanone 1 crystallizes in the orthorhombic space group Pbca with a = 9.413(2) Å, b = 10.787(2) Å, and c = 33.702(5) Å, while bis(ortho-nitro) derivative, 2,6-bis-2-nitro(benzylidene)cyclohexanone in monoclinic P21/n space group with a = 8.482(2) Å, b = 13.435(2) Å, c = 15.377(3) Å, and β = 92.96(2)°. In both compounds the olefinic bonds are in E-configuration, and the cyclohexyl rings adopt a sofa conformation. The phenyl rings are not coplanar with the planes of C=C–C(=O)–C=C fragments; the dihedral angles between these planes are 14.25(11) and 19.37(11)° in 1 and 60.50(6) and 63.26(6)° in 2. This twist might be regarded as the effect of the repulsive interactions between the hydrogen atoms from phenyl and cyclohexyl rings, and much larger values in 2 are certainly connected with the presence of nitro group in ortho-positions of the phenyl ring. It seems that, because of the lack of specific interactions the close packing requirements and the van der Waals forces are main factors determining the crystal packing. The phenyl rings are not coplanar with the planes of C=C–C(=O)–C=C fragments as the effect of the repulsive interactions between the hydrogen atoms from phenyl and cyclohexyl rings .

  在氯化锡存在下合成了两种α,α′-双取代的亚苄基环己酮，并通过 X 射线衍射测定了它们的晶体结构。双（对甲）衍生物 2,6-双-4-甲基（亚苄基）环己酮 1 在正交空间群 Pbca 中结晶，a = 9.413(2) 埃，b = 10.787(2) 埃，c = 33。702(5) 埃，而双(正硝基)衍生物 2,6-双-2-硝基(亚苄基)环己酮在单斜 P21/n 空间群中，a = 8.482(2) 埃，b = 13.435(2) 埃，c = 15.377(3) 埃，β = 92.96(2)°。在这两种化合物中，烯烃键均呈 E 型构象，环己基环则呈sofa 型构象。苯基环与 C=C-C(=O)-C=C 片段的平面不共面；这些平面之间的二面角在 1 中分别为 14.25(11)°和 19.37(11)°，在 2 中分别为 60.50(6)°和 63.26(6)°。看来，由于缺乏特定的相互作用，紧密堆积的要求和范德华力是决定晶体堆积的主要因素。苯基环与 C=C-C(=O)-C=C 片段的平面不共面，这是苯基环和环己基环的氢原子之间排斥作用的结果。
• A facile synthesis of α,α′-bis(substituted-benzylidene)-cycloalkanones and substituted-benzylidene heteroaromatics: utility of NaOAc as a catalyst for aldol-type reaction
  作者：A.F.M. Motiur Rahman、Byeong-Seon Jeong、Dong Hyeon Kim、Jung Ki Park、Eung Seok Lee、Yurngdong Jahng

  DOI：10.1016/j.tet.2007.01.020

  日期：2007.3

  Utility of NaOAc in glacial HOAc as a catalyst for aldol-type condensation reactions was examined. Reactions of cycloalkanones and selected heteroaromatics with various aldehydes in the presence of NaOAc in glacial HOAc provided alpha,alpha-bis(substituted-benzylidene)cycloalkanones and substituted-benzylidene heteroaromatics, respectively, in good yields. (c) 2007 Elsevier Ltd. All rights reserved.
• KONSTANTINOVA, A. V.;MIXALINA, T. V.;FOKIN, E. P., IZV. CO AN CCCP. XIM. H,(1989) N, S. 57-61
  作者：KONSTANTINOVA, A. V.、MIXALINA, T. V.、FOKIN, E. P.

  DOI：——

  日期：——
• Synthesis of SrCO₃ Nanoparticles Supported on Montmorillonite as Efficient Catalyst in the Preparation of α, ά-bis(substituted benzylidene) cycloalkanones
  作者：Enayatollah Sheikhhosseini、Azim Mohammadpour

  DOI：10.2174/1570178619666220314145346

  日期：2022.11

  analysis (XRD), scanning electron microscopy (SEM), and pore size distribution analysis. Crossed-aldol condensation of an aromatic aldehyde with cycloalkanone in the presence of these nanoparticles produced α, ά-bis(substituted-benzylidene) cycloalkanones in good yields without using any solvent. The present method is operationally simple and dosed not use organic solvent, which makes the process environmentally

  摘要：本研究采用可控、简便的微波法将Sr(NO3)2负载于天然膨润土上合成了SrCO3@蒙脱土纳米复合材料。SrCO3@蒙脱石纳米粒子的特性通过红外光谱 (IR)、能量色散 X 射线分析 (EDX)、X 射线衍射分析 (XRD)、扫描电子显微镜 (SEM) 和孔径分布等先进技术进行鉴定分析。在这些纳米颗粒的存在下，芳香醛与环烷酮的交叉醛醇缩合以良好的收率产生α，α-双（取代的亚苄基）环烷酮，而无需使用任何溶剂。本方法操作简单，不使用有机溶剂，对​​环境无害。