2-(2-fluorophenyl)-4,5-dihydro-1H-imidazole | 124314-68-7

• 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: 2-(2-fluorophenyl)-4,5-dihydro-1H-imidazole
• 英文别名: (2-o-fluorophenyl)-1H-imidazoline；2-(o-fluorophenyl)-1H-imidazoline
• CAS: 124314-68-7
• 化学式: C₉H₉FN₂
• 分子量: 164.182
• InChiKey: ZSLVJWBCLUSUOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  对氯苯甲酸甲酯 、 2-(2-fluorophenyl)-4,5-dihydro-1H-imidazole 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以21%的产率得到5-(4-Chloro-phenyl)-9-fluoro-2,5-dihydro-3H-imidazo[2,1-a]isoindol-5-ol
  参考文献：
  名称：

  Mazindol Analogues as Potential Inhibitors of the Cocaine Binding Site at the Dopamine Transporter

  摘要：

  A series of mazindol. (2) and homomazindol (3) analogues with a variety of electron-donating and electron-withdrawing groups in the pendant aryl group and the benzo ring C, as well as H, methoxy, and alkyl groups replacing the hydroxyl group were synthesized, and their binding affinities at the dopamine transporter (DAT) on rat or guinea pig striatal. membranes were determined. Several active analogues were also evaluated for their ability to block uptake of DA, 5-HT, and NE and inhibit binding of [I-125] RTI-55 at HEK-hDAT, HEK-hSERT, and HEK-hNET cells. Mazindane (26) was found to be a pro-drug, oxidizing (5-H --> 5-OH) to mazindol on rat striatal membranes and HEk-hDAT cells. The 4',7,8-trichloro analogue (38) of mazindol was the I most potent and selective ligand. for HEK-hDAT cells (DAT K-i = 1.1 nM; SERT/DAT 1283 and NET/DAT = 38). Experimental results strongly favor the cyclic or ol tautomers of 2 and 3 to bind more, tightly at the DAT than the corresponding keto tautomers.

  DOI：

  10.1021/jm010302r
• 作为产物：
  描述：

  2-(2-Fluoro-phenyl)-imidazolidine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 various solvent(s) 为溶剂， 生成 2-(2-fluorophenyl)-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  One-pot synthesis of imidazolines from aldehydes: detailed study about solvents and substrates

  摘要：

  Imidazolines were prepared in one-pot operation from aldehydes and diamines through oxidation of aminal intermediates by NBS. This method could be applied to various aromatic and aliphatic aldehydes and N-nonsubstituted and N-monosubstituted 1,2-diamines. Furthermore, it was found that CH2Cl2 could be altered to TBME, a more environmentally friendly solvent, in the reaction using N-nonsubstituted 1,2-diamines. The reaction conditions were very mild and chemoselective. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.11.007

文献信息

• Synthesis and pharmacological evaluation of imidazoline sites I1 and I2 selective ligands
  作者：Maria Anastassiadou、Saı̈da Danoun、Louis Crane、Geneviève Baziard-Mouysset、Marc Payard、Daniel-Henri Caignard、Marie-Claire Rettori、Pierre Renard

  DOI：10.1016/s0968-0896(00)00280-7

  日期：2001.3

  heterocyclic-imidazoline compounds have been prepared and evaluated in vitro as imidazoline sites (I1 and I2) and alpha-adrenergic (alpha1 and alpha2) receptor ligands. Their pKi values indicate that linkage of the imidazoline moiety at the 2-position with an aromatic substituent dramatically decreases alpha-adrenergic affinity. I1 sites are more accessible by phenyl imidazolines substituted by a methyl or a methoxy

  已经制备了几种系列的2-芳基或杂环-咪唑啉化合物，并在体外评估为咪唑啉位点（I1和I2）和α-肾上腺素能（α1和α2）受体配体。它们的pKi值表明2-位咪唑啉部分与芳族取代基的连接显着降低了α-肾上腺素的亲和力。通过在邻位或间位上被甲基或甲氧基取代的苯基咪唑啉更易于接近I1位点。实际上，2-（2'-甲氧基苯基）-咪唑啉（17）是有史以来最好的I1配体之一（pKi = 8.53，I1 / I2> 3388）。另一方面，在对位中存在甲基时，I 2选择性增加。原始化合物2-（3'-氟-4'-甲苯基）-咪唑啉（31）是I2位点的新有效配体，具有高选择性（pKi = 8。
• Effect of ortho-substituents on the stereochemistry of 2-(o-substituted phenyl)-1H-imidazoline–palladium complexes
  作者：Zhibin Gan、Kenjiro Kawamura、Kazuo Eda、Masahiko Hayashi

  DOI：10.1016/j.jorganchem.2010.05.007

  日期：2010.8

  Palladium complexes composed of [Pd(Ln)2Cl2] (n = 1, 2, 3, 4, 6), [L5a]2[PdCl4] and [Pd(L5b)2], where L1 = 4,5-dihydro-2-phenyl-1H-imidazole (=2-phenyl-1H-imidazoline), L2 = 2-(o-fluorophenyl)-1H-imidazoline, L3 = 2-(o-methylphenyl)-1H-imidazoline, L4 = 2-(o-tert-butylphenyl)-1H-imidazoline, L5a = 2-(o-hydroxyphenyl)-1H-imidazolinium, L5b = 2-(1H-imidazolin-2-yl)phenolate, and L6 = 2-(o-methylphenyl)-1H-imidazole

  由[Pd（Ln）2 Cl 2 ]（n  = 1，2，3，4，6），[ L5a ] 2 [PdCl 4 ]和[Pd（L5b）2 ]组成的钯配合物，其中L1  = 4,5二氢-2-苯基-1- H-咪唑（= 2-苯基- 1 ħ咪唑啉），L2  = 2-（Ô氟苯基）-1 H-咪唑啉，L3  = 2-（邻-甲基苯基）-1 ħ -咪唑啉，L4  = 2-（ø -叔丁基苯基）-1 H-咪唑啉，L5A  = 2-（Ô羟基苯基）-1 ħ -咪唑啉鎓，L5B  = 2-（1 ħ -咪唑啉-2-基）苯酚，和L6  = 2-（邻-甲基苯基）-1 H-咪唑，合成。通过单晶X射线衍射分析表征分离的钯配合物的分子结构。的效果邻对苯环上-取代基的反式-氯几何形状注意到配合物[钯（L1）2氯2 ]图1A和1B，[钯（L2）2氯2] 2和[Pd（L6）2 Cl 2 ] 6，而[Pd（L3）2 Cl 2 ] 3和[Pd（L4）2
• Reactions of some ortho and para halogenated aromatic nitriles with ethylenediamine: selective synthesis of imidazolines
  作者：Louis J. Crane、Maria Anastassiadou、Jean-Luc Stigliani、Geneviève Baziard-Mouysset、Marc Payard

  DOI：10.1016/j.tet.2004.04.075

  日期：2004.6

  The reaction of ethylenediamine (EDA) with ortho and/or para halogenated benzonitriles did not lead to the imidazolines expected: a competitive aromatic nucleophilic substitution (SNAr) was observed instead. The selective synthesis of these imidazolines was performed by nucleophilic addition of EDA to thiobenzamide derivatives. The difference in reactivity between the nitrile and thioamide derivatives

  乙二胺（EDA）与反应邻和/或对位被卤代苄腈没有导致预期的咪唑啉：有竞争力的芳香亲核取代（S Ñ观察到AR）来代替。这些咪唑啉的选择性合成是通过将EDA亲核加成到硫代苯甲酰胺衍生物中来进行的。腈和硫代酰胺衍生物之间的反应性差异是通过RHF / 6-31G **级的前沿轨道方法估算的，该方法预测了取代的硫代苯甲酰胺对EDA亲核加成的反应性更高。
• A mild and efficient one-pot synthesis of 2-dihydroimidazoles from aldehydes
  作者：Hiromichi Fujioka、Kenichi Murai、Yusuke Ohba、Atsushi Hiramatsu、Yasuyuki Kita

  DOI：10.1016/j.tetlet.2005.02.025

  日期：2005.3

  The reactions of various aldehydes and 1,2-diamines followed by NXS treatment proceed at 0 degrees C to give the corresponding dihydroimidazoles in high yields. The reaction is mild, and many functional groups such as halogens, nitrites, and esters can exist. (c) 2005 Elsevier Ltd. All rights reserved.
• Ring interconversion between a 7-membered ring (2,3-dihydro-1,4-benzodiazepine) and a 14-membered ring (2,3,9,10-dibenzo-1,5,8,12-tetra-azacyclotetradeca-4,11-diene)
  作者：Jan Bergman、Anna Brynolf

  DOI：10.1016/s0040-4039(00)99174-3

  日期：1989.1