2,6-bis(4-fluorobenzylidene)cyclohexanone | 395-12-0

• 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(4-fluorobenzylidene)cyclohexanone
• 英文别名: 2,6-Bis[(4-fluorophenyl)methylidene]cyclohexan-1-one
• CAS: 395-12-0
• 化学式: C₂₀H₁₆F₂O
• mdl: MFCD00398762
• 分子量: 310.343
• InChiKey: STPNBQOTKFPYEG-UHFFFAOYSA-N

物化性质

• 熔点：
  157 °C
• 沸点：
  466.9±45.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-bis(4-fluorobenzylidene)cyclohexanone 在 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 苯 为溶剂， 反应 25.0h， 生成 4',11-bis(4-fluorophenyl)-2',5'-diphenyl-2,2',3,4',11,11a-hexahydro-1H-spiro[dibenzo[b,e][1,4]thiazepine-4,3'-pyrazole]
  参考文献：
  名称：

  Structure Determination and Quantum Chemical Analysis of 1,3-Dipolar Cycloaddition of Nitrile Imines and New Dipolarophiles and POM Analyses of the Products as Potential Breast Cancer Inhibitors

  摘要：

  The 1,3-dipolar cycloaddition of nitrile imines to 11-aryl-4-(arylmethylidene)-1,2,3,4,11,11a-hexahydrodibenzo[b,e][1,4]thiazepines possessing exocyclic C=C and endocyclic C=N bonds as dipolarophilic sites showed site selectivity, depending on the type of C-substituent in the nitrile imine. 1,3-Dipolar cycloaddition ofC-aryl nitrile imines occurred selectively to the exocyclic C=C bond, whereas the endocyclic C=N bond was involved in the cycloaddition withC-ethoxycarbonyl nitrile imines. A combination of total energy and molecular orbital plots for the highest occupied and lowest unoccupied molecular orbitals was used to verify the proposed reaction mechanisms and stereoselectivity. Some of the isolated products exhibited moderate to good antitumor activity. The results of POM analysis of the relative cytotoxicity of these new derivatives in comparison to Doxorubicin are also reported.

  DOI：

  10.1134/s1070428020070210
• 作为产物：
  描述：

  环己酮 、 对氟苯甲醛 在 nanometasilica disulfuric acid 作用下， 以 水 为溶剂， 反应 0.23h， 以93%的产率得到2,6-bis(4-fluorobenzylidene)cyclohexanone
  参考文献：
  名称：

  纳米金属二硫酸在水中催化酮与芳香醛的醛醇缩合和醛醇缩合的高效绿色方法

  摘要：

  介绍了在作为非均相催化剂的纳米金属二硫酸（NMSDSA）存在下芳香醛与各种酮的醛醇缩合和交叉醛缩合。根据开发的较早方法，使用便宜且容易获得的起始原料制备催化剂。高活性催化剂在不发生自缩合反应的情况下得到所需醛醇产物的优异产率。反应时间短，步骤和后处理简单，不涉及挥发性或有害有机溶剂。催化剂可以被回收三次，而活性仅略有降低。

  DOI：

  10.1134/s1070363217050292

文献信息

• Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes
  作者：Ibrahim Jantan、Syed Nasir Abbas Bukhari、Nordin Haji Lajis、Faridah Abas、Lam Kok Wai、Malina Jasamai

  DOI：10.1111/j.2042-7158.2011.01423.x

  日期：2012.2.6

  A series of 43 curcumin diarylpentanoid analogues were synthesized and evaluated for their inhibitory effects on the chemiluminescence and chemotactic activity of phagocytes in vitro.

  The effects of the compounds on the respiratory burst of human whole blood and isolated human polymorphonuclear leukocytes (PMNs) were evaluated using a luminol-based chemiluminescence assay and their effect on chemotactic migration of PMNs was investigated using the Boyden chamber technique.

  Compounds 6, 17, 25 and 30 exhibited significant inhibitory activity on the oxidative burst of PMNs. The presence of methoxy groups at positions 2 and 5, and methoxylation and fluorination at positions 4 and 2 of both phenyl rings, respectively, may contribute significantly to their reactive oxygen species inhibition activity. Compounds 7, 17, 18, 24 and 32 showed strong inhibition of the chemotaxis migration of PMNs. Chlorination at various positions of both phenyl rings of cyclohexanone diarylpentanoid resulted in compounds with potent inhibitory effects on PMN migration.

  The results suggest that some of these diarylpentanoid analogues are able to modulate the innate immune response of phagocytes at different steps, emphasizing their potential as a source of new immunomodulatory agents.

  摘要 目的 合成了一系列43个姜黄素二芳基戊酮类似物，并评估它们对体外吞噬细胞化学发光和趋化活性的抑制作用。 方法 使用基于流明的化学发光测定法评估化合物对人全血和分离的人多形核白细胞（PMNs）呼吸爆发的影响，并利用Boyden室技术研究它们对PMNs趋化迁移的影响。 主要发现 化合物6、17、25和30在PMNs的氧化爆发上表现出显著的抑制活性。在两个苯环的2和5位置有甲氧基基团，以及在4和2位置分别有甲氧化和氟化基团的存在，可能会显著促进它们对活性氧化物种的抑制活性。化合物7、17、18、24和32显示出对PMNs趋化迁移的强烈抑制作用。在环己酮二芳基戊酮类似物的两个苯环的不同位置进行氯化，导致化合物对PMN迁移具有强效抑制作用。 结论 结果表明，这些二芳基戊酮类似物中的一些能够调节吞噬细胞的先天免疫反应的不同步骤，强调它们作为新的免疫调节剂来源的潜力。
• 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
• 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。
• Synthesis, characterization, and crystal structures of α, α′-bis(substituted-benzylidene)cycloalkanone derivatives by nano-TiO2/HOAc
  作者：Elham Tabrizian、Ali Amoozadeh、Salman Rahmani、Mehdi Salehi、Maciej Kubicki

  DOI：10.1007/s11164-015-2039-9

  日期：2016.2

  A new and economical synthesis of α, α′-bis(substituted-benzylidene)cycloalkanones has been achieved by the reaction of cycloalkanones with different aromatic aldehydes using nano-TiO2/acetic acid as a catalyst in ethanol under reflux conditions with excellent yields. Five new products and three new single crystal structures are reported.

  通过使用纳米TiO 2 /乙酸作为催化剂，在乙醇中回流条件下，环烷酮与不同的芳族醛反应，在乙醇中回流条件下，以优异的收率实现了一种新的，经济的α，α'-双（取代亚苄基）环烷酮的合成。报告了五种新产品和三种新的单晶结构。
• Solvent-free catalytic preparation of 2,6-dibenzylidenecycloalkanones using 2-hydroxyethylammonium acetate ionic liquid as catalyst
  作者：Li Q. Kang、Yue Q. Cai、Hao Wang、Li H. Li

  DOI：10.1007/s00706-013-1082-8

  日期：2014.2

  AbstractVarious 2,6-dibenzylidenecycloalkanones were readily prepared in a condensation reaction catalyzed by 2-hydroxyethylammonium acetate ionic liquid under solvent-free conditions in excellent yields. The major advantages of the present method are high yields, short reaction times, lack of solvent, simplicity of performance, and low cost. Graphical abstract

  摘要在无溶剂条件下，由乙酸2-羟乙基铵离子液体催化的缩合反应中，很容易制得各种2,6-二亚苄基环烷酮。本方法的主要优点是产率高，反应时间短，溶剂少，性能简单和成本低。 图形概要