2-(4-nitrophenyl)methylimidazoline | 112030-58-7

• 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-(4-nitrophenyl)methylimidazoline
• 英文别名: 2-[(4-Nitrophenyl)methyl]-4,5-dihydro-1H-imidazole
• CAS: 112030-58-7
• 化学式: C₁₀H₁₁N₃O₂
• 分子量: 205.216
• InChiKey: YVRQVZDDBLLPEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  135-137 °C
• 沸点：
  446.1±28.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)methylimidazoline 在 manganese(IV) oxide 作用下， 以20%的产率得到(1H-imidazol-2-yl)(4-nitrophenyl)methanone
  参考文献：
  名称：

  A novel synthetic method for 2-arylmethyl substituted imidazolines and imidazoles from 2-aryl-1,1-dibromoethenes

  摘要：

  Various 2-arylmethylimidazolines were prepared by treating readily available 2-aryl-1, 1-dibromoethenes with ethylenediamine under mild conditions and further converted into the corresponding imidazoles smoothly with Swern oxidation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.035
• 作为产物：
  描述：

  对硝基苯乙腈 在 盐酸 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 1.33h， 生成 2-(4-nitrophenyl)methylimidazoline
  参考文献：
  名称：

  Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

  摘要：

  Benzylimidazolines may represent a class of 5-HT1D ligands that has yet to be exploited. On the basis of a previous report that the 2-(substituted-benzyl)imidazoline alpha-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT1D receptors, we explored the structure-affinity relationships of a series of related derivatives. Each of the aromatic substituents was removed and then reinstated in a systematic manner to determine the influence of the individual substituents on binding. It was found that all of the aromatic substituents of 8 act in concert to impart high affinity. However, although the 3-hydroxy group could be removed without significantly reducing affinity for h5-HT1D (i.e., human 5-HT1D alpha) receptors, this modification reduced h5-HT1B (i.e., human 5-HT1D beta) receptor affinity by nearly 50-fold. The 2,6-dimethyl groups also contribute to binding but seem to play a greater role for h5-HT1B binding than h5-HT1D binding.With the appropriate structural modifications, several compounds were identified that display 20- to >100-fold selectivity for h5-HT1D versus h5-HT1B receptors. Preliminary functional data suggest that these compounds behave as agonists. Given that 5-HT1D agonists are currently being explored for their antimigraine action and that activation of h5-HT1B receptors might be associated with cardiovascular side effects, h5-HT1D-selective agents may offer a new lead for the development of therapeutically efficacious agents.

  DOI：

  10.1021/jm970513p

文献信息

• Carbene-catalyzed enantioselective oxidative coupling of enals and di(hetero)arylmethanes
  作者：Qiao Chen、Tingshun Zhu、Pankaj Kumar Majhi、Chengli Mou、Huifang Chai、Jingjie Zhang、Shitian Zhuo、Yonggui Robin Chi

  DOI：10.1039/c8sc03480j

  日期：——

  An N-heterocyclic carbene-catalyzed direct oxidative coupling of enals and di(hetero)arylmethanes allows for quick access to optical pure benzimidazole-fused lactams.

  通过N-杂环卡宾催化的炔醛和二(杂)芳基甲烷的直接氧化偶联，可以快速获得光学纯的苯并咪唑-融合内酰胺。

• A Tandem Oxidation Procedure for the Conversion of Alcohols into 1,1-Dibromoalkenes
  作者：Richard J. Taylor、Steven A. Raw、Mark Reid、Estelle Roman

  DOI：10.1055/s-2004-820027

  日期：——

  A practical and concise route to dibromoalkenes directly from activated alcohols in good to excellent yields using a new Tandem Oxidation Procedure (TOP) is reported. We also describe the use of these dibromoalkenes as intermediates in a one-pot route to 4,5-dihydro-1H-imidazoles and in the synthesis of bromoalkynes through MTBD-induced elimination.

  报道了使用新的串联氧化程序 (TOP) 直接从活化的醇中获得二溴烯烃的实用且简洁的路线，产率很高。我们还描述了这些二溴烯烃作为中间体的用途，用于 4,5-二氢-1H-咪唑的一锅法以及通过 MTBD 诱导的消除合成溴炔。
• An efficient method for one-carbon elongation of aryl aldehydes via their dibromoalkene derivatives
  作者：Dal Ho Huh、Ji Sang Jeong、Hee Bong Lee、Hoejin Ryu、Young Gyu Kim

  DOI：10.1016/s0040-4020(02)01324-8

  日期：2002.12

  Various aryl aldehydes were efficiently converted into one-carbon extended aryl acetamides or aryl acetic acids through the reaction of their dibromoalkene derivatives with pyrrolidine in the presence of water under very mild conditions.

  通过在非常温和的条件下，在水的存在下，它们的二溴代烯烃衍生物与吡咯烷反应，将各种芳基醛有效地转化为一个碳原子扩展的芳基乙酰胺或芳基乙酸。
• Synthesis of 2-(Benzoylmethylene)imidazolidines and -hexahydropyrimidines by Condensation of Ethyl Benzoylacetimidates With 1,2-Ethanediamine or 1,3-Propandiamine, and Some Addition Reactions
  作者：Zhi-tang Huang、Zhi-rong Liu

  DOI：10.1055/s-1987-27942

  日期：——

  Ethyl benzoylacetimidates react with 1,2-ethanediamine or 1,3-propanediamine in absolute ethanol to afford the 2-(benzoylmethylene)-imidazolidines or -hexahydropyrimidines, respectively. The structure of these products as ketene aminals is confirmed by spectral data. Electrophilic additions of hydrochloric acid and diethyl diazenedicarboxylate to the ketene aminals are also described.

  苯甲酰乙酰亚胺酸乙酯与 1,2-乙二胺或 1,3-丙二胺在绝对乙醇中发生反应，分别生成 2-（苯甲酰亚甲基）咪唑烷或六氢嘧啶。光谱数据证实了这些产物的烯酮胺结构。此外，还介绍了盐酸和重氮二甲酸二乙酯与烯酮氨基化合物的亲电加成。
• Slavica Meri, Lei Longping, Patil Popat N., Kerezy Alex, Feller Dennis R.+, J. Med. Chem, 37 (1994) N 12, S 1874-1881
  作者：Slavica Meri, Lei Longping, Patil Popat N., Kerezy Alex, Feller Dennis R.+

  DOI：——

  日期：——

表征谱图