2-(o-methylphenyl)imidazoline | 57327-93-2

• 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-(o-methylphenyl)imidazoline
• 英文别名: 4,5-dihydro-2-(2-methylphenyl)-1H-imidazole；2-(o-Tolyl)-2-imidazoline；1H-Imidazole, 4,5-dihydro-2-(2-methylphenyl)-；2-(2-methylphenyl)-4,5-dihydro-1H-imidazole
• CAS: 57327-93-2
• 化学式: C₁₀H₁₂N₂
• 分子量: 160.219
• InChiKey: ZNWOXGIEIAGCQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(o-methylphenyl)imidazoline 在 氧气 、 甲烷 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以53%的产率得到(2-o-methylphenyl)-1H-imidazole
  参考文献：
  名称：

  邻位取代基对2-（邻位取代苯基）-1 H-咪唑啉-钯配合物的立体化学的影响

  摘要：

  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

  DOI：

  10.1016/j.jorganchem.2010.05.007
• 作为产物：
  描述：

  2-甲基苯甲醛 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 various solvent(s) 为溶剂， 反应 0.5h， 生成 2-(o-methylphenyl)imidazoline
  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

• Zeolite-catalyzed simple synthesis of different heterocyclic rings, part 2
  作者：Adrienn Hegedüs、Ilona Vígh、Zoltán Hell

  DOI：10.1002/hc.20036

  日期：——

  A simple and environmentally friendly synthesis was developed for the preparation of 2-arylimidazoline derivatives and 2-arylbenzoxazole derivatives using a small pore size zeolite. The similar reaction was not applicable to the preparation of the sulfur-containing analogs cysteamine or 2-aminothiophenol, probably because of a disadvantageous reaction between the zeolite and the thio compound. © 2004

  开发了一种简单且环保的合成方法，用于使用小孔径沸石制备 2-芳基咪唑啉衍生物和 2-芳基苯并恶唑衍生物。类似的反应不适用于含硫类似物半胱胺或2-氨基苯硫酚的制备，可能是因为沸石与硫代化合物之间的反应不利。© 2004 Wiley Periodicals, Inc. 杂原子化学 15:428–431, 2004; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20036
• Antitumor Activity of 5-Aryl-2,3-dihydroimidazo[2,1-a]isoquinolines
  作者：William J. Houlihan、Paul G. Munder、Dean A. Handley、Seung H. Cheon、Vincent A. Parrino

  DOI：10.1021/jm00002a004

  日期：1995.1

  A series of 5-aryl-2,3-dihydroimidazo[2,1-a]isoquinolines previously reported to be platelet activating factor (PAF) receptor antagonists were evaluated for potential antitumor activity. Several compounds, such as the 5-(4'-tert-butylphenyl) (65), 5-[4'-(trimethylsilyl)phenyl] (69), and 5-(4'-cyclohexylphenyl) (71) analogs showed very good cytotoxicity against several tumor cell lines. 5-[4'-(Pipe

  评估了一系列先前报道为血小板活化因子（PAF）受体拮抗剂的5-芳基-2,3-二氢咪唑并[2,1-a]异喹啉的潜在抗肿瘤活性。几种化合物，例如5-（4'-叔丁基苯基）（65），5- [4'-（三甲基甲硅烷基）苯基]（69）和5-（4'-环己基苯基）（71）类似物显示出对几种肿瘤细胞系具有良好的细胞毒性。5- [4'-（哌啶子基甲基）苯基] -2,3-二氢咪唑并[2,1-a]异喹啉（SDZ 62-434，53）在毫克每千克的基础上比临床细胞生长抑制剂edelfosine更有效（1 ）在口服小鼠Meth A纤维肉瘤试验中增加存活率并减少肿瘤体积。它被选作进一步开发，目前正在癌症患者的I期临床试验中。
• 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。
• Selective Tolyl Carbon Alkylation Mediated by Imidazoline‐Directed Lithiation
  作者：Emily F. Calderwood、Nancy E. Forsyth、Alexandra E. Gould

  DOI：10.1081/scc-200030960

  日期：2004.1.1

  Abstract Imidazoline‐directed lithiation of 2‐o‐tolyl‐4,5‐dihydro‐1H‐imidazole and its subsequent treatment with electrophiles yields C‐alkylated products, without the need for a nitrogen protecting group. A variety of electrophiles were used to install aromatic, heteroaromatic, and alkyl substituted moieties.

  摘要 2-o-tolyl-4,5-dihydro-1H-咪唑的咪唑啉定向锂化及其随后用亲电子试剂处理产生C-烷基化产物，无需氮保护基团。使用各种亲电子试剂来安装芳香族、杂芳香族和烷基取代的部分。
• A Convenient Synthesis of Oxazolines and Imidazolines from Aromatic Aldehydes with Pyridinium Hydrobromide Perbromide in Water
  作者：Shinsei Sayama

  DOI：10.1055/s-2006-941597

  日期：2006.6

  Various 2-oxazolines were prepared from aromatic aldehydes and 2-aminoethanol with pyridinium hydrobromide per­bromide in water at room temperature. 2-Imidazolines were also obtained in good yields from aromatic aldehydes and ethylenediamine under the same reaction conditions.

  以吡啶溴氢溴化物为催化剂，室温下在水中用芳香醛和2-氨基乙醇制备了多种2-噁唑啉。在相同反应条件下，芳香醛和乙二胺也能获得较高产率的2-咪唑啉。