3-甲基-5-(苯基甲基)吡啶 | 74271-42-4

• 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
• 中文名称: 3-甲基-5-(苯基甲基)吡啶
• 中文别名: 二(三乙烯醇十二四烷基醚)磷酸酯
• 英文名称: 3-benzyl-5-methylpyridine
• 英文别名: 5-Benzyl-3-methylpyridine
• CAS: 74271-42-4
• 化学式: C₁₃H₁₃N
• 分子量: 183.253
• InChiKey: UCWQMPICSBZRLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 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：

  1,3-dibenzyl-5-methyl-2-(trimethylsilyl)-1,2-dihydropyridine 在 palladium on activated charcoal air 、 氢气 作用下， 以 2,2,2-三氟乙醇 、 甲苯 为溶剂， 反应 28.0h， 以65 mg的产率得到3-甲基-5-(苯基甲基)吡啶
  参考文献：
  名称：

  Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C−H Activation

  摘要：

  A convenient one-pot C-H alkenylation/electrocyclization/aromatization sequence has been developed for the synthesis of highly substituted pyridine derivatives from alkynes and alpha,beta-unsaturated N-benzyl aldimines and ketimines that proceeds through dihydropyridine intermediates. A new class of ligands for C-H activation was developed, providing broader scope for the alkenylation step than could be achieved with previously reported ligands. Substantial information was obtained about the mechanism of the reaction. This included the isolation of a C-H activated complex and its structure determination by X-ray analysis; in addition, kinetic simulations using the Copasi software were employed to determine rate constants for this transformation, implicating facile C-H oxidative addition and slow reductive elimination steps.

  DOI：

  10.1021/ja7104784

文献信息

• Regioselectively Functionalized Pyridines from Sustainable Resources
  作者：Stefan Michlik、Rhett Kempe

  DOI：10.1002/anie.201301919

  日期：2013.6.10

  Ir‐catalyzed dehydrogenative condensation of alcohols and 1,3‐amino alcohol was used to construct pyridine derivatives regioselectively. This method provides access to unsymmetrically substituted pyridines and tolerates a wide variety of functional groups. Three equivalents of H2 are generated per pyridine unit formed and the alcohol substrates become completely deoxygenated.

  充分利用它！醇和1,3-氨基醇的Ir催化脱氢缩合反应用于区域选择性地构建吡啶衍生物。该方法提供了不对称取代的吡啶的途径，并能耐受多种官能团。每个形成的吡啶单元产生三当量的H 2，醇底物完全脱氧。
• Reactions of 1,4-Bis(trimethylsilyl)-1,4-dihydropyridines with Carbonyl Compounds: A New Method for Regioselective Synthesis of 3-Alkylpyridines
  作者：Otohiko Tsuge、Shuji Kanemasa、Toshio Naritomi、Junji Tanaka

  DOI：10.1246/bcsj.60.1497

  日期：1987.4

  A new method for the alkyl group introduction at the 3-position of pyridienes is described: Reductive disilylation of pyridine, its 2-methyl, 3-methyl, and 4-methyl derivatives affords the corresponding 1,4-disilyl-1,4-dihydropyridines. In the presence of a catalytic amount of tetrabutylammonium fluoride, these dihydropyridines smoothly react with a variety of aldehydes and ketones to give 3-alkylpyridines

  描述了在吡啶的 3-位引入烷基的新方法：吡啶的还原二甲硅烷基化，其 2-甲基、3-甲基和 4-甲基衍生物提供相应的 1,4-二甲硅烷基-1,4-二氢吡啶类。在催化量的四丁基氟化铵存在下，这些二氢吡啶与各种醛和酮顺利反应生成 3-烷基吡啶。
• ASK1 inhibitor and preparation method and use thereof
  申请人：FUJIAN COSUNTER PHARMACEUTICAL CO., LTD.

  公开号：US10787435B2

  公开（公告）日：2020-09-29

  The present disclosure relates to a compound as shown in formula (II), a tautomer or a pharmaceutically acceptable salt thereof, and disclosed is the use thereof in preparing a drug for treating an ASK1-associated disease.

  本公开涉及一种如式（II）所示的化合物、其同系物或药学上可接受的盐，并公开了其在制备治疗 ASK1 相关疾病的药物中的用途。
• TSUGE OTOHIKO; KANEMASA SHUJI; NARITOMI TOSHIO; TANAKA JUNJI, BULL. CHEM. SOC. JAP., 60,(1987) N 4, 1497-1504
  作者：TSUGE OTOHIKO、 KANEMASA SHUJI、 NARITOMI TOSHIO、 TANAKA JUNJI

  DOI：——

  日期：——
• ASK1 INHIBITOR AND PREPARATION METHOD AND USE THEREOF
  申请人：Fujian Cosunter Pharmaceutical Co., Ltd.

  公开号：EP3572401B1

  公开（公告）日：2021-09-29