2-((4-bromophenyl)ethynyl)pyridine | 1071795-01-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-((4-bromophenyl)ethynyl)pyridine
• 英文别名: 2-[2-(4-Bromophenyl)ethynyl]pyridine
• CAS: 1071795-01-1
• 化学式: C₁₃H₈BrN
• 分子量: 258.117
• InChiKey: OTGIBWZJRLCFKK-UHFFFAOYSA-N

物化性质

• 沸点：
  366.4±22.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-((4-bromophenyl)ethynyl)pyridine 在 盐酸 作用下， 以 水 为溶剂， 以31%的产率得到
  参考文献：
  名称：

  Photo-dehydro-Diels–Alder reaction of 1-phenyl-2-(pyridyl)acetylenes in acidic aqueous solution

  摘要：

  The photocycloaddition of 1-(4-R-phenyl)-2-(4-pyridyl)acetylenes (R = H, Br, CH3, Cl) and 1-(4-R-phenyl)-2-(2-pyridyl)acetylenes (R = H, Br, Cl) was carried out in acidic aqueous solution. The unexpected photo-dehydro-Diels-Alder reaction of these monomers was observed, and the results show that two monomers react in a head-to-tail manner and lead to the formation of 2-phenyl-1,3-di(pyridyl)naphthalene derivatives. This reaction presents a direct metal-free method to construct the 1,2,3-triaryl substituted naphthalenes from diarylacetylenes. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2013.07.004
• 作为产物：
  描述：

  在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-((4-bromophenyl)ethynyl)pyridine
  参考文献：
  名称：

  Photo-dehydro-Diels–Alder reaction of 1-phenyl-2-(pyridyl)acetylenes in acidic aqueous solution

  摘要：

  The photocycloaddition of 1-(4-R-phenyl)-2-(4-pyridyl)acetylenes (R = H, Br, CH3, Cl) and 1-(4-R-phenyl)-2-(2-pyridyl)acetylenes (R = H, Br, Cl) was carried out in acidic aqueous solution. The unexpected photo-dehydro-Diels-Alder reaction of these monomers was observed, and the results show that two monomers react in a head-to-tail manner and lead to the formation of 2-phenyl-1,3-di(pyridyl)naphthalene derivatives. This reaction presents a direct metal-free method to construct the 1,2,3-triaryl substituted naphthalenes from diarylacetylenes. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2013.07.004

文献信息

• A Direct, Copper-Catalyzed Functionalization of Pyridines with Alkynes
  作者：Bruce Arndtsen、Ramsay Beveridge

  DOI：10.1055/s-0029-1218632

  日期：2010.3

  provides a route to access these products directly from terminal alkynes and the parent pyridine, and without prefunctionalization of the pyridine core. In addition, (Z)-alk-2-enylpyridines can be prepared via a related procedure. These reactions are used to synthesize a number of new alkynyl- and alkenyl­-substituted pyridines in one pot. pyridine - copper - catalytic - alkyne - alkene

  提出了一种一锅铜催化的方法来构建2-炔基吡啶。这提供了直接从末端炔烃和母体吡啶获得这些产物的途径，而无需对吡啶核进行预官能化。另外，（Z）-烷-2-烯基吡啶可通过相关方法制备。这些反应用于在一个罐中合成许多新的炔基和烯基取代的吡啶。 吡啶-铜-催化-炔-烯烃
• 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）。
• A facile protocol for copper‐free palladium‐catalyzed Sonogashira coupling in aqueous media
  作者：Da‐Young Jung、Soo Youl Park、Seung‐Hoi Kim

  DOI：10.1002/bkcs.12432

  日期：2022.1

  combination of a readily available palladium catalyst and an eco-friendly basic aqueous solution of room-temperature ionic liquid, choline hydroxide (ChOH), was used in a facile protocol alternative to the Sonogashira coupling reaction, alkynylation of aryl halides in the absence of a copper cocatalyst and an external base. The dual nature of ChOH to act as a base and a green solvent played a crucial role in

  容易获得的钯催化剂和环境友好的室温离子液体碱性水溶液氢氧化胆碱 (ChOH) 的组合被用于替代 Sonogashira 偶联反应的简便方案，即在不存在芳基卤化物的情况下进行炔基化铜助催化剂和外部碱。ChOH 作为碱和绿色溶剂的双重性质在催化循环中起着至关重要的作用。尽管反应结果很大程度上取决于底物，但偶联反应在确定的条件下有效地进行以形成 Csp  Csp2 键。
• Pyridyl Directed Catalyst-Free <i>trans</i>-Hydroboration of Internal Alkynes
  作者：Kang Yuan、Naoya Suzuki、Soren K. Mellerup、Xiang Wang、Shigehiro Yamaguchi、Suning Wang

  DOI：10.1021/acs.orglett.5b03698

  日期：2016.2.19

  trans-hydroboration of internal alkynes at room temperature with 9-BBN, producing five-membered BN-heterocycles. Contrary to conventional cis-hydroboration, we demonstrate that the introduction of a pyridyl group switches the stereoselectivity of the reaction. A hydride migration mechanism has been proposed and supported by DFT calculations for the trans-hydroboration. This new hydroboration approach

  我们报告了内部炔烃在室温下与9-BBN的直接反式氢硼化反应的第一个例子，产生了五元BN-杂环。与常规的顺-硼氢化相反，我们证明了吡啶基的引入改变了反应的立体选择性。氢化物迁移机制已经提出，并通过理论计算所支持的反式-hydroboration。这种新的硼氢化方法可以轻松构建新的蓝色荧光BN杂环化合物。
• WO2008/125599
  申请人：——

  公开号：——

  公开（公告）日：——