(4-叔丁基-2,6-二甲基苯基)乙腈 | 84803-57-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-叔丁基-2,6-二甲基苯基)乙腈
• 中文别名: 4-叔丁基-2,6-二甲基苯基乙腈
• 英文名称: 4-tert-butyl-2,6-dimethylphenylacetonitrile
• 英文别名: 2-(4-Tert-butyl-2,6-dimethylphenyl)acetonitrile
• CAS: 84803-57-6
• 化学式: C₁₄H₁₉N
• mdl: MFCD00546812
• 分子量: 201.312
• InChiKey: ZUXNULGHCOXCFL-UHFFFAOYSA-N

物化性质

• 熔点：
  90℃ (ethanol )
• 沸点：
  169-170 °C(Press: 23 Torr)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  (4-叔丁基-2,6-二甲基苯基)乙腈 在 10% palladium on active carbon 氢气 作用下， 以 甲醇 为溶剂， 以76%的产率得到2-(4-叔丁基-2,6-二甲基苯基)乙胺
  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
• 作为产物：
  描述：

  1-叔丁基-3,5-二甲苯 在 盐酸 、 乙醇 、 zinc(II) chloride 作用下， 生成 (4-叔丁基-2,6-二甲基苯基)乙腈
  参考文献：
  名称：

  Buu-Hoi; Cagniant, Bulletin de la Societe Chimique de France, 1942, vol. <5> 9, p. 889,892

  摘要：

  DOI：

文献信息

• [EN] IMIDAZOLES WITH SEROTONIN RECEPTOR BINDING ACTIVITY<br/>[FR] IMIDAZOLES A ACTIVITE DE FIXATION DU RECEPTEUR DE LA SEROTONINE
  申请人：ALLELIX BIOPHARMACEUTICALS INC.

  公开号：WO1998012183A1

  公开（公告）日：1998-03-26

  (EN) This invention relates to compounds having serotonin receptor binding activity, to pharmaceutical compositions containing them and to their medical use, particularly in the treatment of CNS conditions. Described herein are compounds which have general formula (I), wherein R1 is selected from H, C1-6alkyl and benzyl; R2 is selected from H and C1-6alkyl; R3 is selected from H and C1-6alkyl; R4 is selected from C1-6alkyl and halo; R5 is selected from H and OH; and salts, hydrates and solvates thereof. Also described is the use of these compounds as pharmaceuticals to treat indications where stimulation of subtypes of the serotonin receptor is implicated, such as migraine.(FR) L'invention porte sur des composés présentant une activité de fixation du récepteur de la sérotonine, sur des préparations pharmaceutiques les contenant et sur leurs utilisations médicales notamment pour le traitement des troubles du SNC, ainsi que sur leurs sels, hydrates et solvates. Lesdits composés répondent à la formule générale (I) dans laquelle: R1 est sélectionné parmi H, C1-6 alkyle et benzyle; R2 est sélectionné parmi H et C1-6 alkyle; R3 est sélectionné parmi H et C1-6 alkyle; R4 est sélectionné parmi C1-6 alkyle et halo; R5 est sélectionné parmi H et OH. L'invention porte également sur l'utilisation de ces composés comme produits pharmaceutiques pour traiter les cas où la stimulation des sous-types du récepteur de la sérotonine est en cause, tels que la migraine.

  本发明涉及具有5-羟色胺受体结合活性的化合物，包含它们的药物组成物以及它们在治疗中枢神经系统疾病方面的医学用途。本文描述了通式（I）的化合物，其中R1选自H、C1-6烷基和苄基；R2选自H和C1-6烷基；R3选自H和C1-6烷基；R4选自C1-6烷基和卤素；R5选自H和OH；以及它们的盐、水合物和溶剂化物。还描述了将这些化合物用作药物，以治疗与5-羟色胺受体亚型刺激有关的症状，例如偏头痛。
• BE633799
  申请人：——

  公开号：——

  公开（公告）日：——
• Imidazoline-modified benzylimidazolines as h5-HT1D/1B serotonergic ligands
  作者：Thomas Prisinzano、Ho Law、Małgorzata Dukat、Abdelmalik Slassi、Neil MaClean、Lidia Demchyshyn、Richard A. Glennon

  DOI：10.1016/s0968-0896(00)00275-3

  日期：2001.3

  Sumatriptan, a h5-HT1D and h5-HT1B receptor agonist used clinically as a migraine-abortive, produces certain side effects thought to result from its affinity for h(5)-HT1B receptors. The present investigation extends our work with benzylimidazolines as novel non-tryptamine h5-(HT1D/1B) ligands. The effect of N-methylation, N-benzylation, ring-aromatization, and variation of the imidazoline ring on affinity both at h5-HT1D and h5-HT1B receptors was examined. Several compounds were identified with good affinity and enhanced(i.e., > 100-fold) h5-HT1D versus h5-HT1B selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• US2868802
  申请人：——

  公开号：——

  公开（公告）日：——
• US5969137A
  申请人：——

  公开号：US5969137A

  公开（公告）日：1999-10-19