2-m-tolyl-2-Imidazoline | 27423-82-1

• 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-m-tolyl-2-Imidazoline
• 英文别名: 2-(m-tolyl)-4,5-dihydro-1H-imidazole；2-(3-methylphenyl)imidazoline；2-m-tolyl-4,5-dihydro-1H-imidazole；2-m-Tolyl-4,5-dihydro-1H-imidazol；2-(m-Tolyl)-Δ²-imidazolin；2-m-Tolyl-2-imidazolin；2-(3-methylphenyl)-4,5-dihydro-1H-imidazole
• CAS: 27423-82-1
• 化学式: C₁₀H₁₂N₂
• mdl: MFCD09802162
• 分子量: 160.219
• InChiKey: FAZYMPYKTJYGNR-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-m-tolyl-2-Imidazoline 在 palladium diacetate 、 氯化铵 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  A simple two-step access to diversely substituted imidazo[4,5-b]pyridines and benzimidazoles from readily available 2-imidazolines

  摘要：

  We discovered a facile rearrangement of N-(hetero)aryl 2-imidazolines into diversely substituted imidazo[4,5-b]pyridines and benzimidazoles, under Bechamp reduction conditions. Combined with the earlier reported protocol for Pd-catalyzed (hetero)arylation of 2-imidazolines, it provides a simple two-step access to a range of compounds based on these medicinally important heterocyclic cores. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.036
• 作为产物：
  描述：

  3-甲基苯甲酸甲酯 以73%的产率得到
  参考文献：
  名称：

  PISKOV V. B.; KASPEROVICH V. P.; YAKOVLEVA L. M., XIMIYA GETEROTSIKL. SOEDIN., 1976, HO 8, 1112-1118

  摘要：

  DOI：

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。
• Synthesis of tetrazoles, triazoles, and imidazolines catalyzed by magnetic silica spheres grafted acid
  作者：Ruihang Jiang、Hong-Bin Sun、Shuang Li、Kun Zhan、Junjie Zhou、Lei Liu、Kai Zhang、Qionglin Liang、Zhangpei Chen

  DOI：10.1080/00397911.2018.1510007

  日期：2018.10.18

  tetrazoles, triazoles, and imidazolines. The magnetic silica sphere grafted sulfonic acid (MSS-SO3H) is suitable for the synthesis of 1,2,3-triazole via the cycloaddition of nitroalkene with NaN3, whereas the zinc-modified silica sphere catalyst (MSS-SO3Zn) is more suitable for the synthesis of tetrazoles. The MSS-SO3Zn catalyst also works well for the synthesis of 2-substituted imidazoline via the condensation

  摘要 磁分离催化剂用于合成含氮杂环，包括四唑、三唑和咪唑啉。磁性二氧化硅球接枝磺酸（MSS-SO3H）适用于硝基烯烃与NaN3环加成合成1,2,3-三唑，而锌改性二氧化硅球催化剂（MSS-SO3Zn）更适用于四唑类化合物的合成。MSS-SO3Zn 催化剂也适用于通过腈与乙二胺缩合合成 2-取代咪唑啉。MSS-SO3H 和 MSS-SO3Zn 催化剂都可以通过磁铁轻松回收，无需进一步繁琐活化即可重复使用。图形概要
• 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。
• New One-Step Synthesis of 2-Aryl-1H-Imidazoles: Dehydrogenation of 2-Aryl-Δ2-Imidazolines with Dimethylsulfoxide
  作者：Maria Anastassiadou、Geneviève Baziard-Mouysset、Marc Payard

  DOI：10.1055/s-2000-8237

  日期：——

  A new one-step method for the preparation of 2-aryl-1H-imidazoles 3, based on the DMSO dehydrogenation of 2-aryl-Δ2-imidazolines, is described. A comparative study between DMSO and 10% Pd/C, the best known catalyst employed in this transformation, has also been developed. Both protocols were carried out at 120°C for 48 hours.

  描述了一种新的一步法制备2-芳基-1H-咪唑的3，基于对2-芳基-Δ2-咪唑啉的DMSO脱氢作用。还开展了DMSO与10% Pd/C（在这一转化中使用的最佳催化剂）之间的比较研究。两种方法均在120°C下进行48小时。
• Isoform-selective inhibitory profile of 2-imidazoline-substituted benzene sulfonamides against a panel of human carbonic anhydrases
  作者：Claudiu T. Supuran、Stanislav Kalinin、Muhammet Tanç、Pakornwit Sarnpitak、Prashant Mujumdar、Sally-Ann Poulsen、Mikhail Krasavin

  DOI：10.1080/14756366.2016.1178248

  日期：2016.11.1

  of novel benzene sulfonamides (previously evaluated as selective cyclooxygenase-2 inhibitors) has been profiled against human carbonic anhydrases I, II, IV and VII in an attempt to observe the manifestation of the well established "tail" approach for designing potent, isoform-selective inhibitors of carbonic anhydrases (CAs, EC 4.2.1.1). The compounds displayed an excellent (pKi 7-8) inhibitory profile

  有人针对人类碳酸酐酶I，II，IV和VII进行了一系列新颖的苯磺酰胺（先前被评估为选择性环氧合酶-2抑制剂）的尝试，以观察建立有效的“尾巴”方法来设计有效的同工型的表现。 -碳酸酐酶的选择性抑制剂（CA，EC 4.2.1.1）。这些化合物对CA II（胞质抗青光眼和抗水肿生物学靶标）和CA VII（也被认为与癫痫和神经性疼痛有关的胞质靶标）表现出出色的（pKi 7-8）抑制作用。 （1-2个数量级）对胞质同工型CA I和膜结合同工型CA IV的选择性。CA II和CA IV（两者都是催化活性同工型，