2-溴-4-乙烯基吡啶 | 697300-78-0

• 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: 2-溴-4-乙烯基吡啶
• 英文名称: 2-bromo-4-vinylpyridine
• 英文别名: 2-bromo-4-ethenylpyridine
• CAS: 697300-78-0
• 化学式: C₇H₆BrN
• 分子量: 184.035
• InChiKey: OHAOVNXYYOWZJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• 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-溴-4-乙烯基吡啶 在 1,2,2,6,6-五甲基哌啶 、 palladium diacetate 、 三(邻甲基苯基)磷 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  5-Substituted Derivatives of 6-Halogeno-3-((2-(S)-azetidinyl)methoxy)pyridine and 6-Halogeno-3-((2-(S)-pyrrolidinyl)methoxy)pyridine with Low Picomolar Affinity for α4β2 Nicotinic Acetylcholine Receptor and Wide Range of Lipophilicity:  Potential Probes for Imaging with Positron Emission Tomography

  摘要：

  Potential positron emission tomography (PET) ligands with low picomolar affinity at the nicotinic acetylcholine receptor (nAChR) and with lipophilicity (log D) ranging from -1.6 to +1.5 have been synthesized. Most members of the series, which are derivatives of 5-substituted-6-halogeno-A-85380, exhibited a higher binding affinity at alpha4beta2-nAChRs than epibatidine. An analysis, by molecular modeling, revealed an important role of the orientation of the additional heterocyclic ring on the binding affinity of the ligands with nAChRs. The existing nicotinic pharmacophore models do not accommodate this finding. Two compounds of the series, 6-[F-18]-fluoro-5-(pyridin-3-yl)-A-85380 ([F-18]31) and 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2- [F-18]-fluoropyridin-5-yl)pyridine) ([F-18]35), were radiolabeled with F-18. Comparison of PET data for [F-18]31 and 2-[F-18]FA shows the influence of lipophilicity on the binding potential. Our recent PET studies with [F-18]35 demonstrated that its binding potential values in Rhesus monkey brain were ca. 2.5 times those of 2-[F-18]FA. Therefore, [F-18]35 and several other members of the series, when radiolabeled, will be suitable for quantitative imaging of extrathalamic nAChRs.

  DOI：

  10.1021/jm030432v
• 作为产物：
  描述：

  2-溴-4-碘吡啶 、 三丁基乙烯基锡 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 以75.2%的产率得到2-溴-4-乙烯基吡啶
  参考文献：
  名称：

  5-Substituted Derivatives of 6-Halogeno-3-((2-(S)-azetidinyl)methoxy)pyridine and 6-Halogeno-3-((2-(S)-pyrrolidinyl)methoxy)pyridine with Low Picomolar Affinity for α4β2 Nicotinic Acetylcholine Receptor and Wide Range of Lipophilicity:  Potential Probes for Imaging with Positron Emission Tomography

  摘要：

  Potential positron emission tomography (PET) ligands with low picomolar affinity at the nicotinic acetylcholine receptor (nAChR) and with lipophilicity (log D) ranging from -1.6 to +1.5 have been synthesized. Most members of the series, which are derivatives of 5-substituted-6-halogeno-A-85380, exhibited a higher binding affinity at alpha4beta2-nAChRs than epibatidine. An analysis, by molecular modeling, revealed an important role of the orientation of the additional heterocyclic ring on the binding affinity of the ligands with nAChRs. The existing nicotinic pharmacophore models do not accommodate this finding. Two compounds of the series, 6-[F-18]-fluoro-5-(pyridin-3-yl)-A-85380 ([F-18]31) and 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-(2- [F-18]-fluoropyridin-5-yl)pyridine) ([F-18]35), were radiolabeled with F-18. Comparison of PET data for [F-18]31 and 2-[F-18]FA shows the influence of lipophilicity on the binding potential. Our recent PET studies with [F-18]35 demonstrated that its binding potential values in Rhesus monkey brain were ca. 2.5 times those of 2-[F-18]FA. Therefore, [F-18]35 and several other members of the series, when radiolabeled, will be suitable for quantitative imaging of extrathalamic nAChRs.

  DOI：

  10.1021/jm030432v

文献信息

• Modular Photocatalytic Synthesis of α-Trialkyl-α-Tertiary Amines
  作者：J. Henry Blackwell、Georgia R. Harris、Milo A. Smith、Matthew J. Gaunt

  DOI：10.1021/jacs.1c07402

  日期：2021.10.6

  platform, an extensive investigation of the substrate scope, and preliminary investigation of some of the mechanistic features of this distinct photocatalytic process. We believe this transformation will provide convenient access to previously unexplored α-trialkyl-α-tertiary amine scaffolds that should be of considerable interest to practitioners of synthetic and medicinal chemistry in academic and industrial

  显示 α-三烷基-α-叔胺基序的分子提供了进入生物相关化学空间的重要和多功能领域的途径，但通过现有的合成方法难以进入。在这里，我们报告了一种操作简单的多组分方案，用于合成一系列功能和结构多样的 α-三烷基-α-叔胺，该方案利用三种容易获得的组分：二烷基酮、苄胺和烯烃。该策略依赖于使用可见光介导的光催化与现成的 Ir(III) 配合物，将全烷基酮亚胺物种单电子还原为 α-氨基自由基中间体；α-氨基自由基与多种烯烃进行 Giese 型加成，形成 α-三烷基-α-叔胺中心。该过程的机理被认为是通过整个氧化还原中性途径进行的，该途径涉及亚胺的光催化氧化还原中继，该亚胺由起始的胺-酮缩合产生，一直到亚胺衍生产物。这是可能的，因为中间支架中苄胺组分的存在驱动了 Giese 加成后的 1,5-氢原子转移步骤，形成稳定的苄基 α-氨基自由基，从而能够关闭光催化循环。这些研究详细介绍了反应平台的演变、对底物
• 一种喹唑啉酮类化合物及其制备方法
  申请人：河北科技大学

  公开号：CN111116552B

  公开（公告）日：2022-10-11

  本发明涉及化学合成技术领域，具体公开一种喹唑啉酮类化合物及其制备方法。所述喹唑啉酮类化合物，其结构如式(Ⅰ)所示，其中，R1为氢、卤素、甲氧基、甲基、硝基或三氟甲基；R2为或R3为氢、卤素、甲氧基或甲基。本发明提供了一种新型结构的喹唑啉酮类化合物，丰富了喹唑啉酮类化合物的种类，为发展抗炎、抗肿瘤、抗惊厥或抗真菌药物提供了一种新化合物，对于研究该类化合物的活性以及扩大该类化合物在医学领域和工业生产上的应用具有十分重要的意义，为研究具有独特生理活性的新型药物提供了基础。
• Scandium-catalyzed Michael addition of quinazolinones and vinylazaarenes
  作者：Zhiguang Zhang、Siwei Dai、Ling Li、Chenyu Jia、Yong Zhang、Hao Li

  DOI：10.1016/j.tetlet.2020.151926

  日期：2020.6

  We described a novel scandium-catalyzed selective Michael addition of quinazolinones and vinylazaarenes. The protocol proceeds smoothly to give diverse quinazolinone derivatives in moderate to excellent yields. The high practicality of this protocol was proved by excellent chemo selectivity and broad substrate and functional group compatibility.

  我们描述了一种新颖的scan催化的喹唑啉酮和乙烯基氮杂芳烃的选择性迈克尔加成反应。该方案顺利进行，以中等至极好的收率得到了各种喹唑啉酮衍生物。该方案的高度实用性由出色的化学选择性以及广泛的底物和官能团相容性证明。
• Efficient synthesis of 6-chloro-3-((2-(S)-azetidinyl)methoxy)-5-((E)-2-(2-[18F]fluoropyridin-4-yl)vinyl)pyridine([18F]NIDA 52289), a very high affinity radioligand for nicotinic acetylcholine receptors
  作者：Yi Zhang、Andrew W. Hall、Andrew G. Horti

  DOI：10.1002/jlcr.824

  日期：2004.5

  6-Chloro-3-((2-(S)-azetidinyl)methoxy)-5-((E)-2-(2-[18F]fluoropyridin-4-yl)vinyl)pyridine ([18F]NIDA 52289), a very high affinity radioligand for studying nicotinic acetylcholine receptors (nAChRs) by positron-emission tomography, was synthesized through Kryptofix 222 assisted no-carrier-added nucleophilic [18F]fluorination of 6-chloro-3-((1-(tert-butoxycarbonyl)-2-(S)-azetidinyl)methoxy)-5-((E)-2-(2-bromo

  6-氯-3-((2-(S)-氮杂环丁烷基)甲氧基)-5-((E)-2-(2-[18F]氟吡啶-4-基)乙烯基)吡啶([18F]NIDA 52289)是一种用于通过正电子发射断层扫描研究烟碱型乙酰胆碱受体 (nAChR) 的高亲和力放射性配体，通过 Kryptofix 222 辅助无载体添加的亲核 [18F] 氟化 6-氯-3-((1-(tert-丁氧羰基)-2-(S)-氮杂环丁烷基)甲氧基)-5-((E)-2-(2-溴吡啶-4-基)乙烯基)吡啶，然后进行酸性脱保护。放射合成的总放射化学产率为 10%（未衰减校正），比放射性在 93-326 GBq/µmol（2.5-8.8 mCi/µmol）范围内，放射化学纯度大于 99%。版权所有 © 2004 John Wiley & Sons, Ltd.
• MINERALOCORTICOID RECEPTOR ANTAGONISTS
  申请人：GUO Xin

  公开号：US20120289551A1

  公开（公告）日：2012-11-15

  Mineralocorticoid receptor antagonists, of which the following is exemplary.

  翻译结果：矿物质皮质激素受体拮抗剂，以下是其中的代表。