1-(2-cyclopropyl-2-oxoethyl)pyridinium bromide | 239792-95-1

• 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: 1-(2-cyclopropyl-2-oxoethyl)pyridinium bromide
• 英文别名: 1-(2-cyclopropyl-2-oxoethyl)pyridin-1-iumbromide；1-cyclopropylcarbonyl-methylpyridinium bromide；1-Cyclopropylcarbonylmethylpyridinium bromide；1-cyclopropyl-2-pyridin-1-ium-1-ylethanone;bromide
• CAS: 239792-95-1
• 化学式: Br*C₁₀H₁₂NO
• 分子量: 242.115
• InChiKey: KVNSNOXJDWFPJT-UHFFFAOYSA-M

物化性质

• 熔点：
  160-162 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -2.04
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  21
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-cyclopropyl-2-oxoethyl)pyridinium bromide 、 but-2-enedioic acid diethyl ester 在 tetrakispyridinecobalt(II) di(chromate) 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以58%的产率得到diethyl 3-cyclopropylcarbonylindolizine-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of indolizine derivatives incorporating a cyclopropylcarbonyl group against Hep-G2 cancer cell line

  摘要：

  Indolizine and annulated indolizine derivatives incorporating a cyclopropylcarbonyl group were synthesized in a one pot procedure by the tanden reactions of [3 + 2] cycloaddition of the corresponding N-ylide with electron deficient alkene. Seventeen indolizine derivatives were reported for the first time. All the compounds were examined for their antiproliferative activity against the human hepatocellular liver carcinoma (Hep-G2) cell line by MTT method. Among the compounds tested, 5a, 5d, 5g and 5j showed the most favorable activities with IC50 values of 0.39, 0.48, 0.29 and 0.20 mu g/mL. Especially, compound 5j displayed potent antiproliferative activities with IC50 value of 0.20 mu g/mL, and showed significant EGFR kinase inhibitory activity with IC50 value of 0.085 mu M. Docking simulations of 5j were carried out to illustrate the binding mode of the molecular into the EGFR active site. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.02.056
• 作为产物：
  描述：

  吡啶 、 2-溴-1-环丙基乙酮 以 二甲基亚砜 为溶剂， 反应 5.0h， 生成 1-(2-cyclopropyl-2-oxoethyl)pyridinium bromide
  参考文献：
  名称：

  由吡啶盐制备4,5-二取代1,2,3-三氮唑的方法

  摘要：

  本发明涉及一种合成4,5‑二取代1,2,3‑三氮唑类化合物的方法，所述的方法为：以吡啶、卤代烃、磺酸酯、醛和叠氮化钠为原料，一锅法、室温反应；该合成方法无需含金属的催化剂，具有合成产物的收率高、反应条件温和、官能团兼容性好等优点；本发明提供的方法操作步骤简单，反应条件温和且底物适用范围广；该方法具有创新性及潜在的实用价值；适合工业化生产。

  公开号：

  CN108358859A

文献信息

• N-Heterocyclic Carbene-Catalyzed Annulation of Ylides with Ynals: Direct Access to α-Pyrones
  作者：Ming Lang、Qianfa Jia、Jian Wang

  DOI：10.1002/asia.201800595

  日期：2018.9.4

  We herein report an N‐Heterocyclic Carbene (NHC)‐catalyzed annulation of ylides with ynals that provides an efficient protocol to make 4,6‐disubstituted α‐pyrones. This method affords a variety of α‐pyrones in good to high yields as well as broad substrate scope and good functional group tolerance.

  我们在此报告了N-杂环卡宾（NHC）催化的带有芳基的酰基化物环化，提供了制备4,6-二取代的α-吡喃酮的有效方法。该方法可提供高产率到高产率的各种α-吡喃酮，以及广泛的底物范围和良好的官能团耐受性。
• Streptogramin derivatives, preparation method and compositions containing same
  申请人：Aventis Pharma S.A.

  公开号：US20020151676A1

  公开（公告）日：2002-10-17

  Group B streptogramin derivatives of general formula (I): 1 wherein Ra, Rb, Rc, Rd, R 1 , R 2 and Y are as defined in the description, including preparation methods and compositions containing same. Such derivatives are particularly useful as antimicrobial agents, optionally combined with at least one group A streptogramin derivative.

  通式（I）的B组链霉素衍生物：其中Ra、Rb、Rc、Rd、R1、R2和Y如描述中所定义，包括制备方法和含有同样衍生物的组合物。这种衍生物特别有用作为抗微生物药物，可选择性地与至少一种A组链霉素衍生物组合使用。
• Synthesis of 2,3-bifunctional imidazo[1,2-a]pyridines through cycloadditions of pyridinium ylides with N-cyano-4-methyl-N-phenylbenzenesulfonamide
  作者：Gu Zhan、Hongli Zhao、Dong-Ai Li、Yuling Wu、Huaying Fang、Cheng Peng、Bo Han

  DOI：10.1016/j.tetlet.2022.154295

  日期：2023.1

  In this work, we developed a [3 + 2] cycloadditions/oxidation reaction of pyridinium ylides with N-cyano-4-methyl-N-phenylbenzenesulfonamide for the synthesis of 2,3-bifunctional imidazo[1,2-a]pyridines. The N-cyano-4-methyl-N-phenylbenzenesulfonamide serves as an activated nitrile, exhibiting higher activity than common alkyl or aryl nitrile in the reaction. The strategy features high chemoselectivity

  咪唑并[1,2- a ]吡啶因其在药物化学中的广泛应用而被公认为“药物偏见”。在这项工作中，我们开发了吡啶叶立德与N -氰基-4-甲基- N -苯基苯磺酰胺的 [3 + 2] 环加成/氧化反应，用于合成 2,3- 双功能咪唑并 [1,2- a ] 吡啶。N-氰基-4-甲基-N-苯基苯磺酰胺作为活性腈，在反应中表现出比普通烷基腈或芳基腈更高的活性。该策略具有高化学选择性、易于获取的材料和广泛的底物范围。放大反应证明了该方法的实用性，咪唑并[1,2- a]吡啶类产品可以很容易地转化为它们的衍生物。
• Catalyst‐free oxidative [3+2]‐annulation of (2‐nitroethene‐1,1‐diyl)bis(methylsulfane) and pyridinium ylides: Efficient synthesis of (methylsulfanyl)indolizines heterocycles
  作者：Yuce Chen、Yuxin Liu、Hongchen Yang、Zhong Li、Xiaoyong Xu

  DOI：10.1002/jhet.4703

  日期：2023.11

  A facile and efficient protocol has been developed for the synthesis of (methylsulfanyl)indolizine derivatives via oxidative [3+2]-annulation of bis(methylthio)-2-nitroethylen(BMTNE) and pyridinium ylides under K2CO3. The target products could be obtained in moderate to good yields.

  通过双(甲硫基)-2-硝基乙烯(BMTNE)和吡啶叶立德在K 2 CO 3下的氧化[3+2]环化，开发了一种简便有效的方案，用于合成(甲基硫基)中氮茚衍生物。可以以中等至良好的产率获得目标产物。
• Reactions of <i>o</i>-Quinone Methides with Pyridinium Methylides: A Diastereoselective Synthesis of 1,2-Dihydronaphtho[2,1-<i>b</i>]furans and 2,3-Dihydrobenzofurans
  作者：Vitaly A. Osyanin、Dmitry V. Osipov、Yuri N. Klimochkin

  DOI：10.1021/jo400621r

  日期：2013.6.7

  A simple, general route to the 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans substituted at C-2 by an acyl or aryl group, starting from phenolic Mannich bases and pyridinium ylides, has been developed. The mechanism of the reaction is believed to involve the formation of the o-quinone methide intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecular nucleophilic substitution.