4-cyclopentyl-2-methylpyridine | 856834-16-7

• 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: 4-cyclopentyl-2-methylpyridine
• CAS: 856834-16-7
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: FIYRWUYUYPWDSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  4-cyclopent-1-enyl-2-methyl-pyridine 在 溶剂黄146 、 铂 作用下， 生成 4-cyclopentyl-2-methylpyridine
  参考文献：
  名称：

  The Emmert Reaction in the Synthesis of Alkyl- and Cycloalkylpyridines¹

  摘要：

  DOI：

  10.1021/ja01114a024

文献信息

• 8-AZABICYCLO[3.2.1]OCTANE-8-CARBOXAMIDE DERIVATIVE
  申请人：Horiuchi Yoshihiro

  公开号：US20120225876A1

  公开（公告）日：2012-09-06

  Disclosed is a compound represented by formula (1) or a pharmacologically acceptable salt thereof (In the formula, A represents a group that is represented by formula (A-1); R 1a and R 1b may be the same or different and each independently represents a C 1-6 alkyl group which may be substituted by one to three halogen atoms; m and n each independently represents an integer of 0-5; X 1 represents a hydroxyl group or an aminocarbonyl group; Z 1 represents a single bond or the like; and R 2 represents an optionally substituted C 1-6 alkyl group, an optionally substituted C 6-10 aryl group or the like.)

  公开了一种由公式(1)表示的化合物或其药理可接受的盐(在公式中，A代表由公式(A-1)表示的基团；R1a和R1b可以相同或不同，每个独立地表示一个可以由一个到三个卤素原子取代的C1-6烷基；m和n各自独立地表示0-5之间的整数；X1代表羟基或氨基甲酰基；Z1代表单键等；R2代表一个可选地取代的C1-6烷基，一个可选地取代的C6-10芳基等)。
• Mechanochemical Magnesium-Mediated Minisci C–H Alkylation of Pyrimidines with Alkyl Bromides and Chlorides
  作者：Chongyang Wu、Tao Ying、Xinjie Yang、Weike Su、Alexandr V. Dushkin、Jingbo Yu

  DOI：10.1021/acs.orglett.1c02241

  日期：2021.8.20

  A novel method to synthesize 4-alkylpyrimidines by the mechanochemical magnesium-mediated Minisci reaction of pyrimidine derivatives and alkyl halides has been reported. The reaction process operates with a broad substrate scope and excellent regioselectivity under mild conditions with no requirement of transition-metal catalysts, solvents, and inert gas protection. The practicality of this protocol

  已经报道了一种通过嘧啶衍生物和烷基卤化物的机械化学镁介导的 Minisci 反应合成 4-烷基嘧啶的新方法。该反应过程底物范围广，区域选择性好，条件温和，不需要过渡金属催化剂、溶剂和惰性气体保护。该协议的实用性已通过大规模合成、机械化学产品衍生化和抗疟药物乙胺嘧啶的制备得到证明。
• Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling
  作者：Eric C. Hansen、Changfeng Li、Sihang Yang、Dylan Pedro、Daniel J. Weix

  DOI：10.1021/acs.joc.7b01334

  日期：2017.7.21

  importance, the synthesis of alkylated heterocycles from the cross-coupling of Lewis basic nitrogen heteroaryl halides with alkyl halides remains a challenge. We report here a general solution to this challenge enabled by a new collection of ligands based around 2-pyridyl-N-cyanocarboxamidine and 2-pyridylcarboxamidine cores. Both primary and secondary alkyl halides can be coupled with 2-, 3-, and 4-pyridyl

  尽管它们很重要，但是从路易斯碱性氮杂芳基卤化物与烷基卤化物的交叉偶联中合成烷基化杂环仍然是一个挑战。我们在这里报告了基于围绕2-吡啶基-N-氰基羧am和2-吡啶基羧am核的配体的新集合实现的对这一挑战的一般解决方案。伯烷基卤化物和仲烷基卤化物都可以与2-，3-和4-吡啶基卤化物以及其他更复杂的杂环偶联，通常收率很高（41个实例，平均收率69％）。
• Di(2-picolyl)amines as Modular and Robust Ligands for Nickel-Catalyzed C(sp²)–C(sp³) Cross-Electrophile Coupling
  作者：Alexander J. Rago、Aristidis Vasilopoulos、Amanda W. Dombrowski、Ying Wang

  DOI：10.1021/acs.orglett.2c03346

  日期：2022.11.25

  reaction, because noncommercial analogues usually entail challenging syntheses. In this work, di(2-picolyl)amines (DPAs) are explored as an alternative modular ligand class for the nickel-catalyzed aryl–alkyl cross-electrophile coupling. Novel DPA ligands were synthesized directly from inexpensive amine and pyridine building blocks in a single step. This facile synthetic route enabled the parallel synthesis

  镍催化的芳基-烷基偶联反应依赖于使用一组有限的市售双齿含氮配体来实现反应，因为非商业类似物通常需要具有挑战性的合成。在这项工作中，二（2-皮考基）胺 (DPA) 被探索为镍催化的芳基-烷基交叉亲电子偶联的替代模块化配体类别。新型 DPA 配体直接由廉价的胺和吡啶结构单元一步合成。这种简单的合成路线能够平行合成具有不同空间和电子特性的 DPA 配体。从这个配体集合中，C(sp 2 )–C(sp 3) 交叉亲电子偶联在一系列不同分子的交叉偶联中被识别和测试，包括后期功能化的模型示例。
• C-4 Regioselective Alkylation of Pyridines Driven by Mechanochemically Activated Magnesium Metal
  作者：Chongyang Wu、Tao Ying、Hangqian Fan、Chenhui Hu、Weike Su、Jingbo Yu

  DOI：10.1021/acs.orglett.3c00684

  日期：2023.4.14

  Mechanochemically activated magnesium(0) metal as a highly active mediator driving direct C-4–H alkylation of pyridines with alkyl halides has been developed. Excellent regioselectivity and substrate scope, including those containing reducible functionalities, free amines, and alcohols, as well as biologically relevant molecules were achieved to access 4-alkylpyridine products. Preliminary mechanistic

  已经开发出机械化学活化的镁 (0) 金属作为高活性介体，驱动吡啶与烷基卤化物的直接 C-4-H 烷基化。出色的区域选择性和底物范围，包括那些含有可还原官能团、游离胺和醇的底物，以及生物相关分子，以获得 4-烷基吡啶产品。初步的机理研究表明存在自由基-自由基偶联途径。