2,6-di(p-nitrobenzylidene)cyclohexanone | 10321-25-2

• 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-di(p-nitrobenzylidene)cyclohexanone
• 英文别名: α,α'-bis(4-nitrobenzylidene)cyclohexanone；2,6-bis(4'-nitrobenzylidene)cyclohexanone；2,6-bis-(4-nitrobenzylidene)cyclohexanone；2,6-bis(4-nitrobenzylidene)cyclohexanone；2,6-di(4-nitrobenzylidene)cyclohexanone；2,6-bis(4-nitrobenzal)cyclohexanone；2,6-Bis(4'-nitro benzylidene)cyclohexanone；2,6-bis[(4-nitrophenyl)methylidene]cyclohexan-1-one
• CAS: 10321-25-2
• 化学式: C₂₀H₁₆N₂O₅
• mdl: MFCD00358703
• 分子量: 364.357
• InChiKey: IBFHBKDCSZGUSP-UHFFFAOYSA-N

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-di(p-nitrobenzylidene)cyclohexanone 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以62%的产率得到7-(4-nitrobenzylidene)-3-(4-nitrophenyl)-3,3a,4,5,6,7-hexahydro-2H-indazole
  参考文献：
  名称：

  Synthesis and evaluation of DPPH and anti-inflammatory activities of 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives

  摘要：

  A series of thirty three 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives were synthesized and evaluated for inhibitory activities on IFN-gamma/LPS-activated RAW 264.7 cells and DPPH radical scavenging activity. Compounds 8, 9, and 11a demonstrated significant NO inhibitory activity as compared to L-NAME and curcumin with IC50 values of 6.68 +/- A 0.16, 6.09 +/- A 0.46, and 6.84 +/- A 0.12 mu M, respectively. Apparently the suppression upon NO secretion was not due to cell death since the active compounds did not reduce the cell viability in close proximity to the IC50 of NO inhibition. Overall, incorporation of pyrazoline ring as part of the linker chain improved cell viability compared to the 2,6-bisbenzylidenecyclohexanone derivatives. Meanwhile, compound 11 (IC50 = 13.27 +/- A 1.78 mu M) bearing ortho hydroxyls on the aromatic rings recorded the highest radical scavenging activity as compared with quercetin (IC50 = 21.46 +/- A 0.85 mu M).

  DOI：

  10.1007/s00044-010-9521-0
• 作为产物：
  描述：

  环己酮 、 对硝基苯甲醛 在 Ti₂Cl₂(OPrⁱ)₆*2HOPrⁱ 作用下， 以 甲苯 为溶剂， 反应 13.0h， 以94.2%的产率得到2,6-di(p-nitrobenzylidene)cyclohexanone
  参考文献：
  名称：

  烷氧基桥连的双核Ti（IV）簇催化的化学选择性Claisen-Schmidt双取代缩合反应

  摘要：

  链烷酮的高效和化学选择性的α，α'-双取代在有机合成中很重要。在本文中，二聚物钛簇Ti 2 Cl 2（OPr i）6 ·2HOPr i（Ti 2）用于克莱森－施密特缩合反应，以选择性活化包含α，α'-亚甲基和高效和化学选择性生产α，α'-双取代链烷酮。高效和化学选择性可以扩展到各种典型的链烷酮和芳族醛。Ti 2的氧桥联二聚体基序 离子Ti-Cl键负责高效和化学选择性。

  DOI：

  10.1016/j.tet.2016.01.055

文献信息

• Study of in situ generation of carbocationic system from trityl chloride (Ph3CCl) which efficiently catalyzed cross-aldol condensation reaction
  作者：Abdolkarim Zare、Maria Merajoddin、Alireza Hasaninejad、Ahmad Reza Moosavi-Zare、Vahid Khakyzadeh

  DOI：10.1016/j.crci.2012.12.012

  日期：2013.4

  Résumé Organocatalyst trityl chloride (Ph3CCl), by in situ formation of trityl carbocation with inherent instability, efficiently promotes the cross-aldol condensation reaction between cycloalkanones and arylaldehydes in solvent-free and homogeneous media to afford α,α′-bis(arylidene)cycloalkanones in high yields. Moreover, an attractive and plausible mechanism based on observations and the literature is proposed for the reaction.

  简历 组织催化剂三苯氯甲烷（Ph3CCl）通过原位形成固有不稳定的三苯碳正离子，在无溶剂和均相介质中有效促进了环烷酮与芳香醛之间的交叉羟醛缩合反应，以高产率获得了α,α′-双(芳基亚甲基)环烷酮。此外，基于观察结果和文献，为该反应提出了一种吸引人的合理机理。
• Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones
  作者：Salimeh Ahmadi、Abdolkarim Zare、Mina Aali-Hosaini、Maryam Maghsoudi、Shadi Izadpanah、Abolfath Parhami、Maria Merajoddin

  DOI：10.1007/s11164-016-2458-2

  日期：2016.7

  Abstract The aim of this work is to introduce a novel and attractive protic acidic ionic liquid as catalyst for organic synthesis. To achieve this aim, N,N-diethyl-N-sulfoethanaminium hydrogen sulfate [Et3N-SO3H]HSO4} was prepared by reaction of NEt3 with ClSO3H and then with H2SO4. The novel acidic ionic liquid was identified by Fourier-transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR)

  摘要 这项工作的目的是引入一种新颖且有吸引力的质子酸性离子液体作为有机合成的催化剂。为了实现该目的，通过使NEt 3与ClSO 3 H，然后与H 2 SO 4反应，制备了N，N-二乙基-N-磺基硫代硫酸氢铵[Et 3 N-SO 3 H] HSO 4 } 。通过傅立叶变换红外光谱（FT-IR），1 H核磁共振（NMR），13鉴定了新型酸性离子液体13 C NMR和质谱。然后在无溶剂条件下，在芳醛与环烷酮的交叉醇醛缩合反应中检测其催化活性，在短时间后以高收率得到α，α'-双（亚芳基）环烷酮。 图形概要
• Catalyse heterogene par des sels et sans solvant
  作者：J. Boyer、R.J.P. Corriu、R. Perz、C. Reye

  DOI：10.1016/s0022-328x(00)83481-6

  日期：1980.1

  Addition with α,β unsaturated carbonyl compounds gives 1,5 dicarbonyl products. This method is very convenient and the compounds obtained can easily be separated. We assume that the role of the salt in these reactions is to activate the silicon atom by anionic coordination to form a pentacoordinated silicon intermediate.

  甲硅烷基烯醇醚与羰基化合物的反应通过非均相催化而活化。氟化铯是最好的催化剂。不饱和酮是通过使硅烷基烯醇醚与醛和酮缩合反应直接获得的。1,4与α，β不饱和羰基化合物加成，得到1,5二羰基产物。该方法非常方便，并且可以容易地分离得到的化合物。我们假设盐在这些反应中的作用是通过阴离子配位活化硅原子以形成五配位的硅中间体。
• An efficient green chemistry protocol for the synthesis of novel spiropyrrolizidine compounds
  作者：Krishnan Revathy、Appaswami Lalitha

  DOI：10.1039/c3ra44627a

  日期：——

  An efficient method for the synthesis of spirooxindolopyrrolizidine/spirooxindolothiapyrrolizidine by the 1,3-dipolar cycloaddition of azomethine ylides generated via, decarboxylative condensation of 1,2-dicarbonyl compounds and L-proline/L-thiaproline/sarcosine with chalcones at ambient conditions with excellent yields has been described.

  本文描述了一种高效合成螺环吲哚啉并吡咯并[3,2-b]吡啶/螺环吲哚啉并噻吩吡咯并[3,2-b]吡啶的方法，该方法通过1,2-二羰基化合物与L-脯氨酸/L-硫脯氨酸/肌氨酸的去羧缩合反应生成的偶氮甲碱叶立德在室温条件下与查尔酮进行1,3-偶极环加成反应，产率优异。
• Revisit: Eaton’s Reagent Catalyzed Synthesis of Mono and Bis-Chalcone Derivatives
  作者：Shrikrishna. D. Tupare、Santosh V. Nalage、Sharad R. Bobe、Shivshankar N. Hallale、Sheshanath V. Bhosale、Sanjay K. Vyawahare、Satish A. Dake、Sidhanath V. Bhosale、Rajendra P. Pawar

  DOI：10.2174/157017812802139627

  日期：2012.7.1

  Eaton’s reagent efficiently catalyzed the Claisen-Schmidt condensation reaction of aryl aldehydes with aromatic and cyclic ketones under solvent free microwave irradiation conditions to afford mono and bis-chalcone derivatives. The present approach offers several advantages such as shorter reaction times, cleaner reactions, good yields, inexpensive reagent and mild reaction conditions.

  伊顿试剂有效催化了芳烃醛与芳香族和环状酮在无溶剂微波辐射条件下的克莱森-施密特缩合反应，生成单 Chalcone 和双 Chalcone 衍生物。该方法具有多个优点，如反应时间短、反应更干净、产率良好、试剂便宜以及反应条件温和。