1,5-dimethyl-2-phenyl-1H-imidazole | 954213-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,5-dimethyl-2-phenyl-1H-imidazole
• 英文别名: 1,5-Dimethyl-2-phenylimidazole
• CAS: 954213-71-9
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: PRKQQTRCDJAYGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,5-dimethyl-2-phenyl-1H-imidazole 在 四(三苯基膦)钯 copper(l) iodide 、 硫酸 、 四丁基氟化铵 、 碘 、 碘酸 、 silver(l) oxide 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 18.5h， 生成
  参考文献：
  名称：

  Engineering Control over the Conformation of the Alkyne−Aryl Bond by the Introduction of Cationic Charge

  摘要：

  A novel arylene-ethynylene molecule has been synthesized. This molecule is more stable in a coplanar form than in a twisted form as in the cases of typical arylene-ethynylene molecules. When the cationic charge was introduced into the pi-conjugated system, the perpendicularly twisted form became more stable than the coplanar state. The conformational change was controlled by introduction and removal of cationic charge, confirmed by the absorption and fluorescence spectroscopy and DFT calculation.

  DOI：

  10.1021/ol7016966
• 作为产物：
  描述：

  4-甲基-2-苯基咪唑 、 碘甲烷 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以25%的产率得到1,5-dimethyl-2-phenyl-1H-imidazole
  参考文献：
  名称：

  Engineering Control over the Conformation of the Alkyne−Aryl Bond by the Introduction of Cationic Charge

  摘要：

  A novel arylene-ethynylene molecule has been synthesized. This molecule is more stable in a coplanar form than in a twisted form as in the cases of typical arylene-ethynylene molecules. When the cationic charge was introduced into the pi-conjugated system, the perpendicularly twisted form became more stable than the coplanar state. The conformational change was controlled by introduction and removal of cationic charge, confirmed by the absorption and fluorescence spectroscopy and DFT calculation.

  DOI：

  10.1021/ol7016966

文献信息

• Heteroaryl-substituted carboxamides and use thereof for the stimulation of the expression of NO synthase
  申请人：sanofi-aventis

  公开号：EP1939181A1

  公开（公告）日：2008-07-02

  The present invention relates to heteroaryl-substituted carboxamides of the formula I, in which Het, A, X, R1, R2 and R3 have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide (NO) synthase and are valuable pharmacologically active compounds. Specifically, the compounds of the formula I upregulate the expression of the enzyme endothelial NO synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention further relates to processes for the preparation of compounds of the formula I, to pharmaceutical compositions comprising them, and to the use of compounds of the formula I for the manufacture of a medicament for the stimulation of the expression of endothelial NO synthase or for the treatment of various diseases including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency, for example.

  本发明涉及公式I的杂环取代羧酰胺，其中Het、A、X、R1、R2和R3具有索引中指示的含义，这些化合物调节内皮一氧化氮（NO）合酶的转录，并且是有价值的药理活性化合物。具体地，公式I的化合物上调内皮一氧化氮合酶酶的表达，并可应用于需要增加该酶的表达或增加NO水平或正常化降低的NO水平的情况。该发明还涉及公式I化合物的制备方法，包括它们的药物组合物，以及公式I化合物用于制造刺激内皮一氧化氮合酶表达或治疗各种疾病的药物的用途，包括心血管疾病，如动脉粥样硬化、血栓形成、冠状动脉疾病、高血压和心脏功能不全等。
• HETEROARYL-SUBSTITUTED CARBOXAMIDES AND THEIR USE AS PHARMACEUTICALS
  申请人：STROBEL Hartmut

  公开号：US20100016337A1

  公开（公告）日：2010-01-21

  The present invention relates to heteroaryl-substituted carboxamides of the formula I, in which Het, A, X, R 1 , R 2 and R 3 have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide (NO) synthase and are valuable pharmacologically active compounds. Specifically, the compounds of the formula I upregulate the expression of the enzyme endothelial NO synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention further relates to processes for the preparation of compounds of the formula I, to pharmaceutical compositions comprising them, and to the use of compounds of the formula I for the manufacture of a medicament for the stimulation of the expression of endothelial NO synthase or for the treatment of various diseases including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency, for example.

  本发明涉及公式I的杂环取代羧酰胺，其中Het、A、X、R1、R2和R3在权利要求中所示，它们调节内皮型一氧化氮（NO）合酶的转录，并且是有价值的药理活性化合物。具体来说，公式I的化合物上调内皮型一氧化氮合酶的表达，并可应用于需要增加该酶的表达或增加NO水平或恢复降低的NO水平的情况。本发明还涉及制备公式I化合物的方法，包括它们的制药组成物，以及公式I化合物用于制造用于刺激内皮型NO合酶表达或治疗各种疾病的药物，包括心血管疾病，如动脉粥样硬化、血栓形成、冠状动脉疾病、高血压和心力衰竭等。
• Photo-, Solvent-, and Ion-Controlled Multichromism of Imidazolium-Substituted Diarylethenes
  作者：Takuya Nakashima、Kentaro Miyamura、Toshiyuki Sakai、Tsuyoshi Kawai

  DOI：10.1002/chem.200801192

  日期：2009.2.9

  AbstractSeeing red: Imidazolium‐substituted diarylethenes show solvent‐ and ion‐controlled chromisms in addition to reversible photochromic reactions. The shift of equilibrium between two closed‐ring isomers with different π‐conjugation length by interaction with nucleophilic species is responsible for the multichromic property (see scheme).magnified imageCationic diarylethenes with an imidazolium ring are synthesized for the first time. The imidazolium cationic moiety is connected directly to the ethene unit as one of the aryl units that take part in the photoinduced pericyclization reaction. The imidazolium‐substituted diarylethenes undergo reversible photochromic reactions in a variety of organic media, including ionic liquids, even though they have a delocalized cationic charge in one of the five‐membered aromatic rings. The closed‐ring isomer shows solvatochromism depending on the solvent donor numbers. Addition of some tetraalkylammonium salts, such as tetrabutyl ammonium nitrate, into the colored organic solution of diarylethene also causes a color change, indicating its ionochromic property. These solvato‐ and ionochromic properties are considered in connection with the shift of chemical equilibrium between the closed‐ring isomers, one with an extended π‐conjugation system and one with limited π‐conjugation due to the strong interaction with solvent molecules and anions with high donor number.
• US5428037A
  申请人：——

  公开号：US5428037A

  公开（公告）日：1995-06-27
• US5545645A
  申请人：——

  公开号：US5545645A

  公开（公告）日：1996-08-13