5-bromo-2-(1-hexynyl)pyridine | 111770-81-1

• 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: 5-bromo-2-(1-hexynyl)pyridine
• 英文别名: 5-bromo-2-(hex-1-yn-1-yl)pyridine；5-bromo-2-hex-1-ynylpyridine
• CAS: 111770-81-1
• 化学式: C₁₁H₁₂BrN
• 分子量: 238.127
• InChiKey: COXUWNBTCARAHW-UHFFFAOYSA-N

物化性质

• 沸点：
  90-100 °C(Press: 0.01 Torr)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  5-bromo-2-(1-hexynyl)pyridine 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 5-bromo-2-hexylpyridine
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of 6-(Alkyl-heteroaryl)furo[2,3-d]pyrimidin-2(3H)-one Nucleosides and Analogues with Ethynyl, Ethenyl, and Ethyl Spacers at C6 of the Furopyrimidine Core

  摘要：

  Sonogashira coupling strategies were employed to synthesize new furo[2,3-d]pyrimidin-2(3H)-one (FuPyrm) 2'-deoxynucleoside analogues. Partial or complete reduction of ethyne-linked compounds afforded ethenyl-and ethyl-linked derivatives. Levels of inhibition of varicella-zoster virus (VZV), human cytomegalovirus (HCMV), a broad range of other DNA and RNA viruses, and several cancer cell lines were evaluated in cell cultures. The anti-VZV potency decreased with increasing rigidity of the side chain at C6 of the FuPyrm ring in the order dec-1-yn-1-yl < dec-1-en-1-yl < decan-1-yl. In contrast, compounds with a rigid ethynyl spacer between C6 of the FuPyrm ring and a 4-alkylphenyl moiety were more potent inhibitors of VZV than the corresponding derivatives with an ethyl spacer. Replacement of the phenyl moiety in 6-(4-alkylphenyl) derivatives with a pyridine ring (in either regioisomeric orientation) gave analogues with increased solubility in methanol but reduced anti-VZV potency, and replacement with a pyrimidine ring reduced the anti-VZV activity even further. The pyridine-ring-containing analogues were similar to 20-fold more potent inhibitors of VZV than acyclovir but were similar to 6-fold less potent than BVDU and similar to 60-fold weaker than the most active 6-(4-pentylphenyl) -substituted prototype.

  DOI：

  10.1021/jm070210n
• 作为产物：
  描述：

  2,5-二溴吡啶 、 1-己炔 在 copper(l) iodide 、 palladium(II) trifluoroacetate 、 palladium diacetate 、 二异丙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 以58%的产率得到5-bromo-2-(1-hexynyl)pyridine
  参考文献：
  名称：

  钯催化的2，x-二卤代吡啶类的高度区域选择性2-炔基化

  摘要：

  在CH 3 CN中，在i -Pr 2 NH存在下，Pd（CF 3 COO）2 / CuI / PPh 3催化Pd（CF 3 COO）2 / CuI / PPh 3催化2,4-二溴吡啶，回流24 h，得到2-炔丙基吡啶在i -Pr 2 NH在CH 3 CN中回流24 h的条件下，Pd（OAc）2 / CuI / PPh 3催化Pd（OAc）2 / CuI / PPh 3催化2,3和2,5-二卤代吡啶与芳基乙炔反应。以高至高收率得到2-炔基吡啶。

  DOI：

  10.1016/j.tet.2016.03.027

文献信息

• [EN] SUBSTITUTED DIARYLAMINES AND USE OF SAME AS ANTIOXIDANTS<br/>[FR] DIARYLAMINES SUBSTITUÉES ET UTILISATION DE CELLES-CI EN TANT QU'ANTIOXYDANTS
  申请人：UNIV KINGSTON

  公开号：WO2012162818A1

  公开（公告）日：2012-12-06

  The present invention relates to substituted heteroaromatic dianlamine compounds of Formula I and II, their pharmaceutically acceptable salts, and compositions thereof useful as antioxidants, wherein each of X, Y and Z are independently a carbon or nitrogen atom; R1 and R2 are each independently a hydrogen or an electron donating group, but are not both hydrogen, and wherein R1 and R2 are each bonded to a carbon atom in their own respective aryl ring.

  本发明涉及Formula I和II的替代杂环二胺化合物，它们的药用盐以及作为抗氧化剂有用的组合物，其中X、Y和Z中的每一个都是独立的碳或氮原子；R1和R2分别是氢或电子给体基团，但两者不都是氢，并且R1和R2分别与它们自己各自的芳香环中的碳原子结合。
• 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）。
• Rhodium-Catalyzed Addition of Arylboronic Acids to Alkynyl Aza-Heteroaromatic Compounds in Water
  作者：Mark Lautens、Masahiro Yoshida

  DOI：10.1021/jo0205255

  日期：2003.2.1

  Alkynyl heteroaromatic compounds reacted with arylboronic acids to give addition products in the presence of a rhodium catalyst. The best results were obtained when a novel pyridine-substituted water-soluble phosphine ligand was used. The reactions proceed to give trisubstituted alkenes from various arylboronic acids and alkynyl heteroaromatic compounds with high regioselectivity. Only alkynes with

  炔基杂芳族化合物与芳基硼酸反应，在铑催化剂的存在下得到加成产物。当使用新型吡啶取代的水溶性膦配体时，可获得最佳结果。反应进行以高区域选择性从各种芳基硼酸和炔基杂芳族化合物得到三取代的烯烃。如对螯合控制的加料所预期的那样，只有氮原子在三键附近的炔烃才被转化为相应的烯烃。
• Preparation of Highly Reactive Pyridine- and Pyrimidine-Containing Diarylamine Antioxidants
  作者：Jason J. Hanthorn、Luca Valgimigli、Derek A. Pratt

  DOI：10.1021/jo301013c

  日期：2012.8.17

  produce a library of substituted heterocyclic diarylamines that we have used to provide further insight into the structure–reactivity relationships of these compounds as antioxidants (see the accompanying paper, DOI: 10.1021/jo301012x). The diarylamines were prepared in short, modular sequences from 2-aminopyridine and 2-aminopyrimidine wherein aminations of intermediate pyri(mi)dyl bromides and then

  我们最近报告了对开发新型二芳基胺自由基捕获抗氧化剂（汉索恩（JJ）等。J.上午 化学 Soc。 2012，134（8306-8309），其中我们证明了将环氮掺入二苯胺中可提供在H原子对过氧自由基的转移反应性与对单电子氧化的稳定性之间折衷的化合物。本文中，我们提供了与该报告相关的合成研究的详细信息，已对其进行了实质性扩展，以生成取代的杂环二芳基胺库，我们已使用该库进一步了解了这些化合物作为抗氧化剂的结构-反应性关系（请参阅随附的纸张，DOI：10.1021 / jo301012x）。简而言之，制备了二芳基胺 由2-氨基吡啶和2-氨基嘧啶组成的模块序列，其中中间体吡啶（mi）dyl溴化物的胺化以及然后Pd催化的胺与前体溴化物的交叉偶联反应是生成二芳基胺的关键步骤。发现交叉偶联反应在Pd（η3 -1-PHC 3 ħ 4）（η 5 -C 5 H ^ 5）作为前段催化剂，这给了比常规的Pd源，钯更高的产量2（DBA）3。
• Regioselective Rhodium-Catalyzed Addition of Arylboronic Acids to Alkynes with a Pyridine-Substituted Water-Soluble Ligand
  作者：Mark Lautens、Masahiro Yoshida

  DOI：10.1021/ol010261t

  日期：2002.1.1

  [reaction: see text] Alkynyl heteroaromatic compounds reacted with arylboronic acids to give addition products in the presence of [Rh(COD)Cl](2) and pyridine-substituted water-soluble ligand. The reactions proceed to give trisubstituted alkenes with high regioselectivity.

  [反应：见正文]在[Rh（COD）Cl]（2）和吡啶取代的水溶性配体存在下，炔基杂芳族化合物与芳基硼酸反应生成加成产物。反应进行以得到具有高区域选择性的三取代的烯烃。

表征谱图