2-(2-呋喃基)-4,5-二氢-1H-咪唑 | 40029-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 中文名称: 2-(2-呋喃基)-4,5-二氢-1H-咪唑
• 英文名称: 2-(2-furyl)imidazoline
• 英文别名: 2-Furan-2-yl-4,5-dihydro-1H-imidazole；2-(furan-2-yl)-4,5-dihydro-1H-imidazole
• CAS: 40029-93-4
• 化学式: C₇H₈N₂O
• mdl: MFCD02731093
• 分子量: 136.153
• InChiKey: IOTMYJAUZMRWCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  37.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(2-呋喃基)-4,5-二氢-1H-咪唑 在 2% active carbon-supported palladium 作用下， 以 二苯醚 为溶剂， 反应 2.0h， 以66%的产率得到2-(2-呋喃基)-1H-咪唑
  参考文献：
  名称：

  A convenient procedure for preparing hetarylamides and their analogs by dehydrogenation of the corresponding imidazoles

  摘要：

  Conditions of aromatization of 2-(2-hetaryl)imidazolines and their analogs with various dehydrogenating agents were examined. A new catalytic system, Pd/C-diphenyl oxide, was studied, and the optimal catalyst : imidazoline ratio ensuring formation of 2-substituted imidazoles in high yield was found.

  DOI：

  10.1134/s1070427210060182
• 作为产物：
  描述：

  2-(2-furyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole 以 乙腈 为溶剂， 反应 34.0h， 生成 2-(2-呋喃基)-4,5-二氢-1H-咪唑
  参考文献：
  名称：

  2-（2-杂芳基）咪唑啉的直接金属化研究：一些2,3-二取代的噻吩和呋喃的合成

  摘要：

  已经开发了合成2-（2-杂芳基）咪唑啉（1a-c）的通用方法，随后的金属化研究表明，咪唑啉基团是-金属化的强有力的指导者。硫代中间体（5）和（7）的合成用途已经通过与一系列亲电试剂反应而显示。

  DOI：

  10.1016/s0040-4020(01)80726-2

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。
• Efficient Synthesis of 2-Imidazolines in the Presence of Molecular Iodine Under Ultrasound Irradiation
  作者：Guo-Feng Chen、Hong-Yang Li、Nan Xiao、Bao-Hua Chen、Ya-Li Song、Ji-Tai Li、Zhi-Wei Li

  DOI：10.1071/ch13700

  日期：——

  An efficient one-pot synthesis process for preparing 2-imidazolines from aldehydes and ethylenediamine using molecular iodine and potassium carbonate in absolute ethanol at 25–30°C under ultrasound irradiation is described. The synthetic strategy has the following advantages: mild conditions and low costs requirements, readily available catalyst, short reaction times, simplicity of operation, and good-to-excellent yields.

  本研究介绍了一种高效的单锅合成工艺，该工艺在 25-30°C 超声波照射下，使用分子碘和碳酸钾在绝对乙醇中以醛和乙二胺为原料制备 2-咪唑啉。该合成策略具有以下优点：条件温和、成本要求低、催化剂容易获得、反应时间短、操作简单以及良好的收率。
• Synthesis of furanyl and oxazolyl N-substituted piperidine and imidazoline salts as potential agonists of M1 muscarinic receptors
  作者：Andreina Aguado、John Boulos、Anladys Carreras、Angelica Montoya、Judith Rodriquez

  DOI：10.1002/jhet.5570440644

  日期：2007.11

  Furanyl and oxazolyl N-substituted imidazoline salts were prepared by reacting furanyl and oxazolyl esters with ethylenediamine and trimethyl aluminum, followed by the addition of methyl iodide or hydrogen chloride. The piperidinium salts were prepared by treating furanyl and oxazolyl chlorides with piperidine base, followed by the addition of methyl iodide or hydrogen chloride.

  呋喃基和恶唑基的N-取代的咪唑啉盐是通过使呋喃基和恶唑基的酯与乙二胺和三甲基铝反应，然后加入甲基碘或氯化氢来制备的。通过用哌啶碱处理呋喃基氯化物和恶唑基氯化物，然后添加甲基碘或氯化氢来制备哌啶盐。
• Dual-Role Catalysis by Thiobenzoic Acid in Cα–H Arylation under Photoirradiation
  作者：Fumihisa Kobayashi、Masashi Fujita、Takafumi Ide、Yuta Ito、Kenji Yamashita、Hiromichi Egami、Yoshitaka Hamashima

  DOI：10.1021/acscatal.0c04722

  日期：2021.1.1

  a single-electron reducing agent under photoirradiation from a blue light-emitting diode, in the presence of appropriate electron acceptors, and the resulting sulfur-centered radical species undergoes hydrogen atom abstraction. This dual-role catalysis by TBA enables regioselectivie Cα–H arylation of benzylamines, benzyl alcohols, and ethers, as well as dihydroimidazoles, with cyano(hetero)arenes in

  硫代苯甲酸（TBA）在适当的电子受体的存在下，在蓝色发光二极管的光辐射下可以用作单电子还原剂，并且所得的以硫为中心的自由基物种会经历氢原子的提取。TBA的这种双重作用催化使苄胺，苄醇和醚以及二氢咪唑与氰基（杂）芳烃的区域选择性Cα–H芳基化反应具有很高的收率，而无需过渡金属光催化剂和/或合成方法精致的有机染料。
• Pd-Catalyzed N-arylation of 2-imidazolines Provides Convenient Access to Selective Cyclooxygenase-2 Inhibitors
  作者：Mikhail Krasavin

  DOI：10.2174/1570178611310040002

  日期：2013.5.1

  The re-emergence, in the recent years, of cyclooxygenase as a biological target in therapeutic areas other than inflammation is likely to require new optimized leads, particularly suited for the requirements of specific drug development programs. We developed a convenient synthesis of the known imidazole-based selective COX-2 inhibitors bearing primary sulphonamide and methyl sulfone substituents, via Pd-catalyzed imidazoline N-arylation as a key step, followed by dehydrogenation.

  近年来，环氧化酶作为生物靶点重新出现在炎症以外的治疗领域，这可能需要新的优化线索，特别是适合特定药物开发计划要求的线索。我们开发了一种简便的合成方法，通过钯催化咪唑啉 N-芳基化作为关键步骤，然后进行脱氢反应，合成出含有初级磺酰胺和甲基砜取代基的已知咪唑类选择性 COX-2 抑制剂。