6-[(4-fluoroanilino)methylidene]cyclohexa-2,4-dien-1-one | 3382-62-5

• 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: 6-[(4-fluoroanilino)methylidene]cyclohexa-2,4-dien-1-one
• 英文别名: (E)-2-(((4-fluorophenyl)imino)methyl)phenol；2-((E)-[(4-fluorophenyl)imino]methyl)phenol；2-(4-fluorophenyliminomethyl)phenol；N-(2-hydroxybenzylidene)-4-fluoroaniline；N-(o-hydroxybenzylidene)-p-fluoroaniline
• CAS: 3382-62-5
• 化学式: C₁₃H₁₀FNO
• 分子量: 215.227
• InChiKey: COFLOZFCNFCJFM-OQLLNIDSSA-N

物化性质

• 熔点：
  82.0 to 86.0 °C
• 最大波长(λmax)：
  349nm(MeOH)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  6-[(4-fluoroanilino)methylidene]cyclohexa-2,4-dien-1-one 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.0h， 以60%的产率得到2-(((4-fluorophenyl)amino)methyl)phenol
  参考文献：
  名称：

  Synthesis and structure–antibacterial activity relationship studies of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones

  摘要：

  The synthesis and characterization of a series of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones were presented. Preliminary in vitro antimicrobial activity of the compounds was assessed against a panel of microorganisms including S. aureus, E. faecalis, P. aeruginosa, E. coli, and C. albicans. Some of the compounds exhibited significantly in vitro antimicrobial activity. The pMIC values were correlated with physicochemical descriptors: Hammett substituent constants (sigma (m) and sigma (p) ) and the lipophilic constant (pi). One statistical significant 2D-QSAR model was obtained with para-substituted compounds. The pMIC values were also correlated with some theoretical descriptors as independent variables and four statistical significant 2D-QSAR models were also obtained with meta-substituted compounds.

  DOI：

  10.1007/s00044-010-9457-4
• 作为产物：
  描述：

  水杨醛 、 4-氟苯胺 以 乙醇 为溶剂， 以95%的产率得到6-[(4-fluoroanilino)methylidene]cyclohexa-2,4-dien-1-one
  参考文献：
  名称：

  亚氨基酚铝配合物控制ε-己内酯与d，l-丙交酯的开环均聚和共聚：一种有效的方法，用于定义明确的大分子单体

  摘要：

  包含类型（两个iminophenolate配体的铝络合物p -XC 6 ħ 4 NCHC 6 ħ 4 O- ö）2为AlR”（R'=我（3,4）或R'= O（CH 2）4 OCH =合成了CH 2（5，6），X = H（3，5），F（4，6）），并通过1 H，13 C NMR光谱和X射线晶体学对其进行了表征。AlMe 3与两当量取代的亚氨基酚反应生成五配位的{ONR} 2 AlMe（3，4）复合体。这些甲基络合物与不饱和醇HO（CH 2）4 OCH = CH 2的随后反应，以高收率得到目标化合物5和6。结果表明，所述复合物（3 - 6）在溶液中（NMR）和在固体状态（X射线分析）的单体。评估了配合物5和6对ε-己内酯和d，l-丙交酯的开环聚合（ROP）的催化活性。配合物5与6相比显示出更高的活性，而这两种催化剂均能诱导受控的均相和共聚反应，从而在较大的分子量范围内（M n = 4000–30

  DOI：

  10.1002/pola.27110

文献信息

• The evaluation of the role of C–H⋯F hydrogen bonds in crystal altering the packing modes in the presence of strong hydrogen bond
  作者：Gurpreet Kaur、Sandhya Singh、Amritha Sreekumar、Angshuman Roy Choudhury

  DOI：10.1016/j.molstruc.2015.10.105

  日期：2016.2

  found to form strong O–H⋯N hydrogen bond, but the spatial arrangement of the molecules connected by this hydrogen bond have been found to be controlled by the weak C–H⋯F and C–H⋯O hydrogen bonds, weak C–H⋯π and π⋯π interactions. This manuscript illustrates the importance of several weaker interactions in altering the packing modes in the presence of strong hydrogen bonds.

  摘要 涉及氟的相互作用是当代研究的一个领域。为了阐明强氢键存在下有机化合物中弱 C-H⋯F 氢键和 C-H⋯π 相互作用的重要性，合成了一系列同时具有羟基 (-OH) 和氟取代的 N-亚苄基苯胺，用于结构分析。这些化合物已通过实验性单晶 X 射线衍射分析和计算方法（Gaussian09 和 AIM2000）进行了研究。发现所有分子中存在的羟基形成强的 O-H⋯N 氢键，但发现由这种氢键连接的分子的空间排列受弱 C-H⋯F 和 C- H⋯O 氢键，弱 C–H⋯π 和 π⋯π 相互作用。
• PdCl₂(Ph₃P)₂/Salicylaldimine Catalyzed Diarylation of Anilines with Unactivated Aryl Chlorides
  作者：Xiaochun Tao、Lei Li、Yu Zhou、Xuanying Qian、Min Zhao、Liangzhen Cai、Xiaomin Xie

  DOI：10.1002/cjoc.201700276

  日期：2017.11

  salicylaldimine could be used as a mixed ligand system to obtain a high catalytic activity for palladium catalyzed diarylation of primary anilines with unactivated aryl chlorides by the synergistic effect of ligands. The activity and selectivity of the catalytic system could be improved by modifying the structure of salicylaldimine. In refluxing o‐xylene, PdCl2(Ph3P)2 with 2,5‐ditrifluoromethyl N‐phenylsalicylaldimine

  三苯基膦和水杨醛亚胺可以用作混合的配体体系，以通过配体的协同作用获得钯催化的伯苯胺与未活化的芳基氯的二芳基化的高催化活性。通过改变水杨醛亚胺的结构可以提高催化体系的活性和选择性。在回流的ø二甲苯，的PdCl 2（PH 3 P）2与2,5- ditrifluoromethyl Ñ苯基水杨醛亚胺大肠菌素对各种苯胺的二芳基化反应显示出很高的效率。催化体系对底物的空间位阻表现出良好的耐受性。简便的催化体系在1,1'-联苯-4,4'-二胺与芳基氯的多重芳基化反应中也能提供N，N，N'，N'-四芳基-1,1'-联苯-4 ，4'-二胺是有机发光二极管（OLED）空穴传输材料的重要中间体。
• (Phenoxyimine)nickel-Catalyzed C(sp2)–C(sp3) Suzuki–Miyaura Cross-Coupling: Evidence for a Recovering Radical Chain Mechanism
  作者：L. Reginald Mills、Eric M. Simmons、Heejun Lee、Eva Nester、Junho Kim、Steven R. Wisniewski、Matthew V. Pecoraro、Paul J. Chirik

  DOI：10.1021/jacs.4c01474

  日期：2024.4.10

  the C(sp2)–C(sp3) Suzuki–Miyaura cross coupling of (hetero)arylboronic acids with alkyl bromides. With 5 mol % of the optimal (MeOMeFI)Ni(Aryl)(DMAP) precatalyst, the scope of the cross-coupling reaction was established and included a variety of (hetero)arylboronic acids and alkyl bromides (>50 examples, 33–97% yield). A β-hydride elimination–reductive elimination sequence from reaction with potassium

  合成了苯氧亚胺 (FI)–镍(II)(2-甲苯基)(DMAP) 化合物，并作为（杂）芳基硼酸与烷基的 C(sp 2 )–C(sp 3 ) Suzuki-Miyaura 交叉偶联的预催化剂进行了评估溴化物。使用 5 mol% 的最佳 (Me OMe FI)Ni(芳基)(DMAP) 预催化剂，建立了交叉偶联反应的范围，包括各种（杂）芳基硼酸和烷基溴（> 50 个示例，33 –97% 的产率）。与异丙醇钾碱反应产生 (FI) 镍 (0) 酸钾的 β-氢化物消除-还原消除序列被确定为负责从烷基溴中提取卤素原子的催化剂活化途径。 NMR 和 EPR 光谱相结合，确定 (FI) 镍 (II)-芳基配合物在催化过程中处于静止状态，没有证据表明存在长寿命有机自由基或奇电子镍中间体。这些数据表明，自由基链是短暂的，很容易终止，并且还支持“恢复自由基链”过程，通过该过程，(FI)镍(II)-芳基化合物不断地（
• Design, synthesis and biological evaluation of imine resveratrol derivatives as multi-targeted agents against Alzheimer's disease
  作者：Su-Yi Li、Xiao-Bing Wang、Ling-Yi Kong

  DOI：10.1016/j.ejmech.2013.10.068

  日期：2014.1

  A series of imine resveratrol derivatives (1-20) have been designed, synthesized, and evaluated as multi-targeted compounds for the treatment of Alzheimer's disease (AD).In vitro studies show that most of the molecules exhibit a significant ability to inhibit self-induced and Cu2+-induced beta-amyloid (A beta(1-42)) aggregation, and to function as potential antioxidants and biometal chelators. In particular, compound 9 is a potential lead compound for AD treatment (for compound 9, IC50 = 14.1 mu M for the antioxidant activity using DPPH free radical method; 64.6% at 20 mu M for self-induced A beta aggregation). Moreover, it is capable of decreasing reactive oxygen species (ROS) induced by Cu-A beta and shows good neuroprotective effects in human SH-SY5Y neuroblastoma cells. Taken together, these results suggest that 9 might be a promising lead compound for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Four<i>N</i>-(2-hydroxybenzylidene)aniline derivatives
  作者：J. Burgess、J. Fawcett、D. R. Russell、S. R. Gilani、V. Palma

  DOI：10.1107/s0108270199008239

  日期：1999.10.15

  The molecular structures of N-(2-hydroxybenzylidene)-4-fluoroaniline, C13H10FNO, N-(2-hydroxybenzylidene)-4-trifluoromethoxyaniline, C14H10F3NO2, N-(2-hydroxy-5-chlorobenzylidene)-4-chloroaniline, C13H9Cl2NO, and N-(2-hydroxybenzylidene)-4-nitroaniline, C13H10N2O3, have been determined. In each case, the conformations are such that the hydroxy group is aligned towards the N atom facilitating a strong intramolecular hydrogen bond.