2-bromo-5-butylpyridine | 856930-23-9

• 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-bromo-5-butylpyridine
• 英文别名: 2-Bromo-5-butylpyridine
• CAS: 856930-23-9
• 化学式: C₉H₁₂BrN
• 分子量: 214.105
• InChiKey: WCEKIZCFCIBLBM-UHFFFAOYSA-N

物化性质

• 沸点：
  271.0±20.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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-bromo-5-butylpyridine 在 copper(l) iodide 、 四(三苯基膦)钯 氢氧化钾 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 5-[2-(5-butylpyrid-2-yl)ethynyl]-1-(2-deoxy-β-D-erythro-pentofuranosyl)uracil
  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：

  5-丁基吡啶-2-羧酸 在 sodium hypobromide 、 乙醚 、 氢溴酸 、 溴 作用下， 生成 2-bromo-5-butylpyridine
  参考文献：
  名称：

  Welkstoffe和Antibiotika。16. Mitteilung。Fusarinsäure-[羧基14 C]和季铵盐Fusarinsäure †

  摘要：

  Fusarinsäurewurde zum 2-Brom-5-n-butyl-pyridin abgebaut; daraus wurdeüberdie Lithium-VerbindungFusarinsäure-[carboxyl- 14 C] hergestellt。铵-衍生的古通量的AusFusarinsäure和Fusarinsäure-amidwurden einigequaternäre。

  DOI：

  10.1002/hlca.19560390126

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AS CCR1 RECEPTOR ANTAGONISTS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES UTILISÉS EN TANT QU'ANTAGONISTES DES RÉCEPTEURS CCR1
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011056440A1

  公开（公告）日：2011-05-12

  Disclosed are CCR1 receptor antagonists of the formula (I) wherein Ar1, Ar2, R1-R3, X and L are disclosed herein. Also disclosed are compositions, methods of making and using compounds of the formula (I).

  揭示了公式（I）中的CCR1受体拮抗剂，其中Ar1、Ar2、R1-R3、X和L在此处披露。还披露了公式（I）化合物的组成、制备方法和使用方法。
• Concise Total Synthesis and Antifungal Activities of Fusaric Acid, a Natural Product
  作者：Bin Bin Huang、Ya Yi Liu、Peng Fei Zhu、Yi Cheng Jiang、Ming-An Ouyang

  DOI：10.3390/molecules25173859

  日期：——

  The total synthesis of a natural product alkaloid fusaric acid (FA), which exhibits herbicide, fungicide, insecticide and even diverse notable pharmacological activities, was accomplished in four steps using commercially available materials. The synthesis, based on a unified and flexible strategy using 6-bromonicotinaldehyde as a common intermediate, is concise, convergent, practical and can be carried

  天然产物生物碱镰刀菌酸 (FA) 的全合成使用市售材料分四步完成，该产物具有除草剂、杀真菌剂、杀虫剂甚至多种显着的药理活性。该合成基于统一和灵活的策略，使用 6-溴烟醛作为常见中间体，简洁、收敛、实用，可以在两克规模上进行。这种方法可以很容易地应用于其类似物的合成。此外，本研究中FA对14种植物病原真菌具有广泛的抑制活性，表明其作为领先化合物，具有进一步开发作为农业杀菌剂的巨大潜力。
• HETEROCYCLIC COMPOUNDS AS CCR1 RECEPTOR ANTAGONISTS
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP2493875A1

  公开（公告）日：2012-09-05
• Synthesis and Antiviral Evaluation of 6-(Alkyl-heteroaryl)furo[2,3-<i>d</i>]pyrimidin-2(3<i>H</i>)-one Nucleosides and Analogues with Ethynyl, Ethenyl, and Ethyl Spacers at C6 of the Furopyrimidine Core
  作者：Morris J. Robins、Ireneusz Nowak、Vivek K. Rajwanshi、Karl Miranda、John F. Cannon、Matt A. Peterson、Graciela Andrei、Robert Snoeck、Erik De Clercq、Jan Balzarini

  DOI：10.1021/jm070210n

  日期：2007.8.1

  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.
• Welkstoffe und Antibiotika. 16. Mitteilung. Fusarinsäure- [carboxyl-¹⁴C] und quaternäre Derivate der Fusarinsäure
  作者：E. Hardegger、E. Nikles

  DOI：10.1002/hlca.19560390126

  日期：——

  Fusarinsäure wurde zum 2-Brom-5-n-butyl-pyridin abgebaut; daraus wurde über die Lithium-Verbindung Fusarinsäure-[carboxyl-14C] hergestellt. Aus Fusarinsäure und Fusarinsäure-amid wurden einige quaternäre Ammonium-Derivate gewonnen.

  Fusarinsäurewurde zum 2-Brom-5-n-butyl-pyridin abgebaut; daraus wurdeüberdie Lithium-VerbindungFusarinsäure-[carboxyl- 14 C] hergestellt。铵-衍生的古通量的AusFusarinsäure和Fusarinsäure-amidwurden einigequaternäre。