2-(cyclohex-1-en-1-ylethynyl)pyridine | 49836-17-1

• 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: 2-(cyclohex-1-en-1-ylethynyl)pyridine
• 英文别名: 1-cyclohexene (2-pyridine) acetylene；2-(2-cyclohexenylethynyl)pyridine；2-cyclohex-1-enylethynyl-pyridine；2-[2-(cyclohexen-1-yl)ethynyl]pyridine
• CAS: 49836-17-1
• 化学式: C₁₃H₁₃N
• 分子量: 183.253
• InChiKey: ZWQFPYQWWDBORG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  2-乙炔基吡啶 在 吡啶 、 正丁基锂 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 2-(cyclohex-1-en-1-ylethynyl)pyridine
  参考文献：
  名称：

  Cyclohexenyl- and dehydropiperidinyl-alkynyl pyridines as potent metabotropic glutamate subtype 5 (mGlu5) receptor antagonists

  摘要：

  Structure-activity relationship studies leading to the discovery of novel mGlu5 receptor antagonists are described. These compounds show high in vitro potency, have good in vivo receptor occupancy, and a reasonable intravenous pharmacokinetic profile. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.099

文献信息

• A Highly Efficient, Practical, and General Route for the Synthesis of (R₃P)₂Pd(0): Structural Evidence on the Reduction Mechanism of Pd(II) to Pd(0)
  作者：Hongbo Li、Gabriela A. Grasa、Thomas J. Colacot

  DOI：10.1021/ol101106z

  日期：2010.8.6

  A highly efficient, practical, and general method was developed to synthesize a family of (R3P)2Pd(0) complexes, using a stoichiometric amount of phosphine ligands and readily available Pd(II) precursors. The stepwise pathway of reducing Pd(II) to Pd(0) was established by isolating two key intermediates. Both [t-Bu2(4-Me2NC6H4)P]2Pd and (t-Bu2NpP)2Pd are new compounds. Preliminary studies on [t-Bu2(4-Me2NC6H4)P]2Pd

  开发了一种高效，实用且通用的方法，使用化学计量的膦配体和易于获得的Pd（II）前体合成（R 3 P）2 Pd（0）配合物家族。通过分离两个关键中间体，建立了将Pd（II）还原为Pd（0）的逐步途径。[ t - Bu 2（4-Me 2 NC 6 H 4）P] 2 Pd和（t- Bu 2 NpP）2 Pd均为新化合物。[ t - Bu 2（4-Me 2 NC 6 H 4）P] 2的初步研究钯已表明，在无铜的Sonogashira偶联中，它是一种非常活泼的催化剂（分离产率为84-95％），其中涉及0.5 mol％催化剂负载量的芳基和杂芳基氯化物。
• Visible-light induced copper(<scp>i</scp>)-catalysed denitrogenative oxidative coupling of hydrazinylpyridines with terminal alkynes
  作者：Vaibhav Pramod Charpe、Aniket A. Hande、Arunachalam Sagadevan、Kuo Chu Hwang

  DOI：10.1039/c8gc01180j

  日期：——

  Visible light mediated copper catalysed denitrogenative oxidative coupling of 2-hydrazinopyridines with terminal alkynes to form 2-(alkyl/arylethynyl) pyridines in the presence of O2 at room temperature is reported with 42 examples. This is the first report on visible light stimulated N2 elimination by an in situ generated copper(II) superoxo/peroxo complex. N2 and water are the only by-products. The

  有42个实例报道了在室温下在O 2存在下可见光介导的铜催化的2-肼基吡啶与末端炔烃的铜催化的脱氮氧化偶联，以形成2-（烷基/芳基乙炔基）吡啶。这是关于通过原位生成的铜（II）超氧/过氧配合物消除可见光刺激的N 2的首次报道。N 2和水是唯一的副产物。绿色化学指标评估表明当前的方法是环保的，并且在经济上可行。该方法可以绿色合成mGluR5受体拮抗剂，2-甲基-6-（苯基乙炔基）吡啶（MPEP）和2-（（3-甲氧基苯基）乙炔基）-6-甲基吡啶（M-MPEP）。
• Transition-Metal-Free BF₃-Mediated Oxidative and Non-Oxidative Cross-Coupling of Pyridines
  作者：Quan Chen、Thierry León、Paul Knochel

  DOI：10.1002/anie.201400750

  日期：2014.8.11

  We report a BF3‐mediated direct alkynylation of pyridines at C(2) by using a variety of alkynyllithium reagents (oxidative cross‐coupling). Moreover, we have developed a novel transition‐metal‐free cross‐coupling method between alkylmagnesium reagents and 4‐substituted pyridines, such as isonicotinonitrile and 4‐chloropyridine, by employing BF3⋅OEt2 as a promoter. The combination of these methods enabled

  我们报告了BF 3介导的吡啶在C（2）上通过使用各种炔基锂试剂（氧化交叉偶联）的直接烷基化。此外，我们通过使用BF 3 OEt 2作为促进剂，在烷基镁试剂与4-取代的吡啶（例如异烟腈和4-氯吡啶）之间开发了一种新型的无过渡金属的交叉偶联方法。这些方法的结合使我们能够有效地制备各种二，三和四取代的吡啶。
• Heck Alkynylation (Copper-Free Sonogashira Coupling) of Aryl and Heteroaryl Chlorides, Using Pd Complexes of <i>t</i>-Bu₂(<i>p</i>-NMe₂C₆H₄)P: Understanding the Structure–Activity Relationships and Copper Effects
  作者：Xiaotao Pu、Hongbo Li、Thomas J. Colacot

  DOI：10.1021/jo302195y

  日期：2013.1.18

  L2Pd(0) and L2Pd(II) complexes, where L=t-Bu-2(p-NMe2C6H4)P, have been identified as efficient catalyst systems for the Heck alkynylation of a variety of aryl bromides (17 examples) and aryl/heteroaryl chlorides (31 examples) with a range of aryl- and alkyl-acetylenes in excellent yields, under relatively low Pd loadings. The single-crystal X-ray structure determination of the presumably active catalytic species, L2Pd(0), was carried out in this study to better understand the superior activity of the current catalyst system from a structure activity relationship point of view. The P-Pd-P bond angle indicates that the complex is bent (174.7 degrees) in comparison to the perfectly linear (180.0 degrees) structure of the analogous Pd(t-Bu3P)(2). Preliminary mechanistic studies on the negative copper effect and substrate effect of aryl acetylenes were conducted to better understand the cross-coupling pathway of Heck alkynylation.
• Zhang, Weiwei; Cheng, Jiang; Huang, Zhengxu, Journal of Chemical Research, 2006, # 12, p. 781 - 782
  作者：Zhang, Weiwei、Cheng, Jiang、Huang, Zhengxu、Zhou, Qingqing、Chen, Xunmin、Qian, Jianzhu

  DOI：——

  日期：——