N(1),N(2)-双(4-氟苯亚甲基)乙烷-1,2-二胺 | 1648-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N(1),N(2)-双(4-氟苯亚甲基)乙烷-1,2-二胺
• 英文名称: N,N'-(ethane-1,2-diyl)bis(1-(4-fluorophenyl)methanimine)
• 英文别名: N(1),N(2)-bis(4-fluorobenzylidene)ethane-1,2-diamine；N,N′-bis(4-fluorobenzylidene)ethylenediamine；N1,N2-bis(4-fluorobenzylidene)ethane-1,2-diamine；N,N'-bis(4-fluorobenzylidene)ethane-1,2-diamine；BFBED；N,N'-Bis-(4-fluorobenzylidene)-ethylenediamine；1-(4-fluorophenyl)-N-[2-[(4-fluorophenyl)methylideneamino]ethyl]methanimine
• CAS: 1648-04-0
• 化学式: C₁₆H₁₄F₂N₂
• 分子量: 272.297
• InChiKey: BUVGSMGTCXQKPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N(1),N(2)-双(4-氟苯亚甲基)乙烷-1,2-二胺 在 甲醇 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 52.0h， 生成 2-(chloromethyl)-1,4-bis(4-fluorobenzyl)piperazine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel cYY analogues targeting Mycobacterium tuberculosis CYP121A1

  摘要：

  The rise in multidrug resistant (MDR) cases of tuberculosis (TB) has led to the need for the development of TB drugs with different mechanisms of action. The genome sequence of Mycobacterium tuberculosis (Mtb) revealed twenty different genes coding for cytochrome P450s. CYP121A1 catalyzes a C-C crosslinking reaction of di-cyclotyrosine (cYY) producing mycocyclosin and current research suggests that either mycocyclosin is essential or the overproduction of cYY is toxic to Mtb. A series of 1,4-dibenzyl-2-imidazol-1-yl-methylpiperazine derivatives were designed and synthesised as cYY mimics. The derivatives substituted in the 4-position of the phenyl rings with halides or alkyl group showed promising antimycobacterial activity (MIC 6.25 mu g/mL), with the more lipophilic branched alkyl derivatives displaying optimal binding affinity with CYP121A1 (Pr-i K-D = 1.6 mu M; Bu-t K-D = 1.2 mu M). Computational studies revealed two possible binding modes within the CYP121A1 active site both of which would effectively block cYY from binding.

  DOI：

  10.1016/j.bmc.2019.02.051
• 作为产物：
  描述：

  对氟苯甲醛 、 乙二胺 以 氯仿 为溶剂， 反应 0.5h， 生成 N(1),N(2)-双(4-氟苯亚甲基)乙烷-1,2-二胺
  参考文献：
  名称：

  [ N，N'-双（4-氟亚苄基）乙二胺]溴（三苯基膦）铜（I）的合成，晶体结构和光致异构化

  摘要：

  标题席夫碱配合物是用于在光生物学过程如视觉中发生的光异构化反应的模型化合物。席夫碱配体和配合物已通过一锅合成法制备。在配合物的晶体结构中，铜具有扭曲的四面体配位。溶液中的光化学研究揭示了时间分辨的光谱变化，这些变化可以通过配位的席夫碱配体的CN键从E构型转变为Z构型来解释。将多元曲线分辨率和非线性最小二乘曲线拟合应用于光谱轮廓可提供光异构化的速率常数为0.11 min -1和0.246的量子产率。

  DOI：

  10.1016/j.poly.2013.06.016
• 作为试剂：
  描述：

  丙烯酸丁酯 、 4-氟苯硼酸 在 bis(triphenylphosphine)nickel(II) chloride 、 N(1),N(2)-双(4-氟苯亚甲基)乙烷-1,2-二胺 、 铁粉 、 potassium iodide 作用下， 以 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 120.0h， 以45%的产率得到n-butyl 3-(4-fluorophenyl)propanoate
  参考文献：
  名称：

  使用镍（I）配合物催化芳基硼酸向α，β-不饱和底物加成1,4-

  摘要：

  使用活化铁从Ni（PPh 3）2 Cl 2原位生成镍（I）配合物，然后使用与N，N'-双（4-氟亚苄基）乙烷-1,2-二胺（BFBED）结合的配合物作为芳基硼酸与α，β-不饱和底物的1,4-加成反应的催化剂。反应进行至完全，不需要添加碱，但是添加碘化钾对于该交叉偶联反应至关重要。此外，实验观察结果表明可能存在Ni（I）–Ni（III）催化循环机制。

  DOI：

  10.1016/j.tetlet.2014.02.046

文献信息

• Design and application of diimine-based copper(<scp>i</scp>) complexes in photoredox catalysis
  作者：Tamás Földesi、Gellért Sipos、Réka Adamik、Bálint Nagy、Balázs L. Tóth、Attila Bényei、Krisztina J. Szekeres、Győző G. Láng、Attila Demeter、Timothy J. Peelen、Zoltán Novák

  DOI：10.1039/c9ob01331h

  日期：——

  Structurally different bis(imino)copper(i) complexes were prepared in a highly modular manner and utilized as copper-based photocatalysts in the ATRA reactions of styrenes and alkyl halides. The new photocatalysts showed good catalytic activity and ensured efficient chemical transformations.

  以高度模块化的方式制备结构不同的双（亚氨基）铜（i）配合物，并将其用作苯乙烯和烷基卤化物的ATRA反应中的铜基光催化剂。新的光催化剂显示出良好的催化活性并确保了有效的化学转化。
• Zn2+-K10-clay (clayzic) as an efficient water-tolerant, solid acid catalyst for the synthesis of benzimidazoles and quinoxalines at room temperature
  作者：Amarajothi Dhakshinamoorthy、Kuppusamy Kanagaraj、Kasi Pitchumani

  DOI：10.1016/j.tetlet.2010.10.146

  日期：2011.1

  protocol is developed in which zinc chloride-exchanged K10-montmorillonite (clayzic) is employed as a Lewis acid catalyst in aqueous media at room temperature for the synthesis of various benzimidazoles and quinoxalines from carbonyl compounds and o-phenylenediamine. Among the various catalysts (including claycop and Zn2+–Y) studied, clayzic produces benzimidazoles and quinoxalines in higher yield, and

  开发了一种非常简单，绿色和有效的方案，其中在室温下，在水性介质中，采用氯化锌交换的K10蒙脱石（粘土）作为路易斯酸催化剂，用于从羰基化合物和邻苯二胺合成各种苯并咪唑和喹喔啉。。在研究的各种催化剂（包括claycop和Zn 2+ -Y）中，clayzic以较高的收率生产苯并咪唑和喹喔啉，并且使用柔性二胺（如乙二胺）只能形成双席夫碱。该协议的其他显着特征包括条件更温和，原子经济，不存在偶联剂以及无浪费。
• Synthesis and Biological Evaluation of Novel Substituted-Imidazolidine Derivatives
  作者：Asif Husain、Rubina Bhutani、Deepak Kumar、Dong-Soo Shin

  DOI：10.5012/jkcs.2013.57.2.227

  日期：2013.4.20

  A series of newer substituted-imidazolidine derivatives 3a-k were synthesized and assayed in vivo to investigate their anti-inflammatory, analgesic and antiulcer activity. The results of biological evaluation revealed that the three compounds, 4-[1,3-bis(4-hydroxy-3-methoxybenzyl)-2-imidazolidinyl]phenyldiethylamine (3g), 4-[1,3-bis(3-Ethoxy-4-hydroxybenzyl)-2-imidazolidinyl] phenyldiethylamine (3h) and 4-(1,3-bis(benzo[d][1,3]dioxol-5-ylmethyl)-4-methylimidazolidin-2-yl)-N,N-diethylbenzenamine (3j) were good in their anti-inflammatory and analgesic actions. Additionally these derivatives showed superior GI safety profile as compared to that of the standard drug in terms of low severity index. The results are statistically treated for its significance.

  研究人员合成了一系列较新的取代咪唑烷衍生物 3a-k，并对其进行了体内试验，以研究它们的抗炎、镇痛和抗溃疡活性。生物学评价结果表明，4-[1,3-双（4-羟基-3-甲氧基苄基）-2-咪唑烷基]苯二乙胺（3g）、4-[1、3-双（3-乙氧基-4-羟基苄基）-2-咪唑烷基]苯基二乙胺（3h）和 4-（1,3-双（苯并[d][1,3]二恶茂-5-基甲基）-4-甲基咪唑烷-2-基）-N,N-二乙基苯胺（3j）具有良好的抗炎和镇痛作用。此外，与标准药物相比，这些衍生物在低严重指数方面显示出更优越的胃肠道安全性。这些结果经统计学处理，具有重要意义。
• Phosphorus–nitrogen compounds part 22. Syntheses, structural investigations, biological activities and DNA interactions of new mono and bis (4-fluorobenzyl) spirocyclophosphazenes
  作者：Aytuğ Okumuş、Zeynel Kılıç、Tuncer Hökelek、Hakan Dal、Leyla Açık、Yağmur Öner、L. Yasemin Koç

  DOI：10.1016/j.poly.2011.08.035

  日期：2011.11

  The reactions of hexachlorocyclotriphosphazene, N3P3Cl6, with mono (1 and 2) and bis(4-fluorobenzyl) diamines (3-5), FPhCH2NH(CH2)(n)NHR (R=H or FPhCH2-), produce mono (1a and 2a) and bis(4-fluorobenzyl) monospirocyclophosphazenes (3a-5a). The tetraaminomonospirocyclophosphazenes (1b-2d) are obtained from the reactions of the partly substituted phosphazenes (1a and 2a) with excess pyrrolidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD), respectively. The tetrachlorobis(4-fluorobenzyl) monospirocyclophosphazenes (4a and 5a) with excess pyrrolidine, morpholine and DASD afford the fully substituted bis(4-fluorobenzyl) monospirocyclophosphazenes (4b, 4d-5d) in boiling THF. In addition, monochlorobis(4-fluorobenzyl) monospirocyclophosphazenes (4e and 41) have also been isolated from the reactions with excess morpholine and DASD in boiling THF. The structural investigations of the compounds have been verified by elemental analyses, MS. FTIR, H-1, C-13, F-19 (for 1d and 2d). P-31 NMR, HSQC and HMBC techniques. The crystal structures of 3a, 4a, 5a and 2b have been determined by X-ray crystallography. The compounds 2a-5a, 1b-2d, 4b, 4d-5d, 4e and 41 have been screened for antibacterial effects on bacteria and for antifungal activity against yeast strains. The compounds 1b and 4b showed antimicrobial activity against three species of bacteria, Bacillus subtilis, Bacillus cereus and Staphylococcus aureus, and two fungi, Candida albicans and Candida tropicalis. Minimum inhibitory concentrations (MIC) were determined for 1b and 4b. The MIC values were found to be 5000 mu M for each bacteria. The most effective compound, 4b has exhibited activity with a MIC of 312 mu M for C albicans and 625 mu M for C. tropicalis. DNA-binding and the nature of the interaction with pBR322 plasmid DNA are studied. All of the compounds induce changes on the DNA mobility and intensity. Prevention of Hind[l] digestion with the compounds indicates that the compounds bind with AT nucleotides in DNA. (C) 2011 Elsevier Ltd. All rights reserved.
• A zeolite promoted expeditious one-pot synthesis of 1-arylmethyl-4,5-dihydro-2-aryl-1H-imidazole
  作者：Ramakanth Pagadala、Jyotsna S. Meshram、Himani N. Chopde、Nagender Reddy Panyala

  DOI：10.1002/jhet.314

  日期：——

  Abstract magnified image A series of 1‐arylmethyl‐4,5‐dihydro‐2‐aryl‐1H‐imidazoles were synthesized expeditiously in good yields from 1,2‐diaminoethane and aromatic aldehydes in the presence of zeolite under microwave irradiation in the absence of solvent. The resulting substituted imidazoles are characterized by 1H and 13C NMR, elemental analysis, and mass spectral data. J. Heterocyclic Chem., (2010)