3-(2,5-dimethylphenyl)pyridine | 69299-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(2,5-dimethylphenyl)pyridine
• CAS: 69299-54-3
• 化学式: C₁₃H₁₃N
• 分子量: 183.253
• InChiKey: XIDYWLKFONVFCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-溴吡啶 、 2,5-dimethylphenylmagnesium bromide 在 bis(triphenylphosphine)nickel(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 3-(2,5-dimethylphenyl)pyridine
  参考文献：
  名称：

  Synthesis and α-adrenergic and I1-imidazoline activity of 3-phenylpiperidines dimethyl-substituted on the phenyl ring

  摘要：

  In a previous study we found that certain 3-phenylpiperidines (PPEs, 5) display a good activity at alpha(2)-adrenergic receptors (alpha(2)-AR), whereas they are completely inactive at alpha(1)-AR. The PPEs 5 are conformationally restricted analogs of the corresponding adrenergic drug with a phenylethylamine structure (PAEs, 4) in which the benzylic hydroxyl group characteristic of the adrenergic catecholamines is not present. The most interesting of the PPEs proved to be the 3-(3,4-dimethylphenyl) substituted compound (5a) which had been found to be essentially inactive at beta(1)- and beta(2)-AR. The methyl groups present on the aromatic ring of 5a are found, albeit in a different position, on the phenyl of alpha(2)-adrenergic agonists with arylimidazolidine and arylimidazole structures. As such PPE 5a provided a unique template for the design of alpha(2)-AR ligands. On the basis of these premises, we synthesized all the possible dimethylphenyl-substituted isomers of PPE 5a. Their activity on alpha(1)- and alpha(2)-AR and on I-1-imidazoline receptors (IR) was evaluated in vitro both by radioligand binding assays and by functional tests on isolated preparation. Two selected PPEs, 5a and 5f, were also tested for their affinity on alpha(2)-AR subtypes. Conformational studies were carried out by means of theoretical calculations, in order to rationalise the results of pharmacological tests at the molecular level. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80016-6

文献信息

• Pd(II)-Catalyzed C3-Selective Arylation of Pyridine with (Hetero)arenes
  作者：Guo-Lin Gao、Wujiong Xia、Pankaj Jain、Jin-Quan Yu

  DOI：10.1021/acs.orglett.5b03712

  日期：2016.2.19

  Palladium catalyzed, nondirected C3-selective arylation of pyridines with arenes and heteroarenes in the presence of 1,10-phenanthroline as the ligand has been developed. The optimized conditions allow for a highly C3-selective arylation of pyridines, affording various 3,3′-bipyridines and 3-arylpyridines.

  在1,10-菲咯啉作为配体的情况下，开发了钯与芳烃和杂芳烃催化的C3选择性非定向芳构化芳基化合物。优化的条件允许吡啶的高度C3选择性芳基化，提供各种3,3'-联吡啶和3-芳基吡啶。
• BENZIMIDAZOLE-PROLINE DERIVATIVES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：US20150166527A1

  公开（公告）日：2015-06-18

  The present invention relates to compounds of the formula (I) wherein Ar 1 , R 1 , R 2 , R 3 , R 4a , R 4b and (R 5 ) n are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as orexin receptor antagonists.

  本发明涉及公式（I）的化合物，其中Ar1，R1，R2，R3，R4a，R4b和（R5）n如描述中所述，以及它们的制备，其药学上可接受的盐，以及它们作为药物的用途，包括含有一个或多个公式（I）化合物的药物组合物，特别是它们作为促进睡眠激素受体拮抗剂的用途。
• Benzimidazole-proline derivatives
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：US11040966B2

  公开（公告）日：2021-06-22

  The present invention relates to compounds of the formula (II) wherein Ar1, R1, R2, R3, R4a, R4b and (R5)n are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (II), and especially to their use as orexin receptor antagonists.

  本发明涉及式 (II) 的化合物 其中 Ar1、R1、R2、R3、R4a、R4b 和 (R5)n 如描述中所述，涉及它们的制备、其药学上可接受的盐及其作为药物的用途、含有一种或多种式 (II) 化合物的药物组合物，特别是它们作为奥曲肽受体拮抗剂的用途。
• Ligand-Promoted C3-Selective Arylation of Pyridines with Pd Catalysts: Gram-Scale Synthesis of (±)-Preclamol
  作者：Mengchun Ye、Guo-Lin Gao、Andrew J. F. Edmunds、P. A. Worthington、James A. Morris、Jin-Quan Yu

  DOI：10.1021/ja209510q

  日期：2011.11.30

  The first example of Pd-catalyzed, C3-selective arylation of unprotected pyridines has been developed by employing a catalytic system consisting of Pd(OAc)(2) and 1,10-phenanthroline. This protocol provides an expeditious route to an important class of 3-arylpyridines and 3-arylpiperidines frequently found in bioactive compounds. A brief synthesis of the drug molecule (+/-)-preclamol is also reported.
• JULLIARD M.; SIV C.; VERNIN G.; METZGER J., HELV. CHIM. ACTA, 1978, 61, NO 8, 2941-2948
  作者：JULLIARD M.、 SIV C.、 VERNIN G.、 METZGER J.

  DOI：——

  日期：——