p-methoxyphenacyl-α-picolinium bromide | 82746-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenacyl-α-picolinium bromide
• 英文别名: 1-[2-(4-Methoxyphenyl)-2-oxoethyl]-2-methylpyridinium bromide；1-(4-methoxyphenyl)-2-(2-methylpyridin-1-ium-1-yl)ethanone;bromide
• CAS: 82746-45-0
• 化学式: Br*C₁₅H₁₆NO₂
• 分子量: 322.202
• InChiKey: YWCASSMCYMTDGP-UHFFFAOYSA-M

物化性质

• 熔点：
  176 °C(Solv: ethanol (64-17-5))

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  p-methoxyphenacyl-α-picolinium bromide 在 正丁基锂 、 四甲基乙二胺 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.25h， 生成 5-(4-chlorophenyl)-2-(4-methoxyphenyl)indolizine
  参考文献：
  名称：

  Synthesis, photophysical, and electrochemical properties of 2,5-diaryl-indolizines

  摘要：

  A variety of novel 2,5-dialyl-indolizines have been prepared through the palladium-catalyzed cross-coupling reactions of organozinc reagents prepared from 2-aryl-indolizines with aromatic halides. The photophysical properties of representative compounds indicate that the 2,5-diaryl-indolizines are promising candidates to be used in optoelectronic devices and biomolecular labeling. In addition, cyclic voltammetry studies of some nitrophenyl-substituted indolizines have shown evidences of an oxidation process without the correspondent reduction peak suggesting a dimerization reaction. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.105
• 作为产物：
  描述：

  碳酸甲丙酯 、 alpha-溴-4-甲氧基苯乙酮 以 丙酮 为溶剂， 生成 p-methoxyphenacyl-α-picolinium bromide
  参考文献：
  名称：

  微波辅助改进区域选择性合成 3-苯甲酰中氮茚衍生物

  摘要：

  开发了一种在微波辐射下通过双组分反应合成 3-苯甲酰中氮氢化合物的高效简便方法。底物适用范围广，在微波辐射下得到目标产物3-苯甲酰中氮，收率为74-89%，并与柱纯化后的常规合成方法进行了收率比较。通过微波辐射合成了不同的新型 3-苯甲酰中氮衍生物。通过1 H-NMR、13 C-NMR 和 HRMS 等光谱分析对新合成的化合物结构进行了表征。

  DOI：

  10.1016/j.molstruc.2023.135561

文献信息

• Nitro- para- and meta- Substituted 2-Phenylindolizines as Potential Antimicrobial Agents
  作者：Claudio L.K. Lins、John H. Block、Robert F. Doerge

  DOI：10.1002/jps.2600710519

  日期：1982.5

  Abstract Some para- and meta -substituted nitro-2-phenylindolizines were prepared and tested as potential antimicrobial agents. The syntheses were accomplished via the Chichibabin-Stepanow synthesis, using the properly substituted α -picoline and phenacyl bromides followed by direct nitration.

  摘要制备了对位和间位取代的硝基-2-苯基吲哚并作为潜在的抗菌剂进行了测试。合成是通过Chichibabin-Stepanow合成完成的，使用适当取代的α-甲基吡啶和苯甲酰溴，然后直接硝化。
• A Practical Parallel Synthesis of 2-Substituted Indolizines
  作者：Wenying Chai、Annette Kwok、Victoria Wong、Nicholas I. Carruthers、Jiejun Wu

  DOI：10.1055/s-2003-42042

  日期：——

  A practical parallel synthesis of 2-substituted indolizines 4 via phase-separation techniques is reported. Their further transformation into indolizidines 5 is also described.

  报告了一种通过相分离技术实现的2-取代吲唑啉4的实用并行合成方法，并描述了它们进一步转化为吲唑啶5的过程。
• Enantioselective Synthesis of 3-Allylindolizines via Sequential Rh-Catalyzed Asymmetric Allylation and Tschitschibabin Reaction
  作者：Ke Li、Changkun Li

  DOI：10.1021/acs.orglett.0c03383

  日期：2020.12.18

  The first highly regio- and enantioselective synthesis of 3-allylindolizines has been developed by the sequential Rh-catalyzed asymmetric allylation and Tschitschibabin reaction. Above the 20:1 branch/linear ratio, up to a 96% yield and 99% ee could be obtained with the help of tert-butyl-substituted chiral bisoxazolinephosphine ligand. In situ generated highly nucleophilic 2-alkylpyridinium ylides

  通过顺序的Rh催化的不对称烯丙基化和Tschitschibabin反应，已经开发出了3-allylindolizines的第一个高度区域和对映选择性的合成。高于20：1的支链/线性比，借助于叔丁基取代的手性双恶唑啉膦配体可以获得高达96％的产率和99％的ee。在环化之前，利用原位产生的高度亲核的2-烷基吡啶鎓烷基化物进行不对称烷基化反应。
• Electrochemical C–H phosphorothiolation of indolizines with thiocyanate and phosphite in one pot
  作者：Chenglong Feng、Haochen Wang、Yuanbin She、Meichao Li、Zhenlu Shen

  DOI：10.1016/j.tet.2024.133911

  日期：2024.4

  A facile and practical protocol for C–H phosphorothiolation of indolizines using thiocyanate as the sulfur source and phosphite as the phosphorylated reagent has been developed. A broad range of substrates were well tolerated and the desired products were obtained in moderate to excellent yields. Moreover, the reaction involved electrochemical thiocyanation of indolizines and a chemical process to construct

  已经开发出一种简便实用的中氮茚的 C-H 硫代磷酸化方案，使用硫氰酸盐作为硫源，亚磷酸盐作为磷酸化试剂。多种底物具有良好的耐受性，并且以中等至优异的产率获得了所需的产物。此外，该反应涉及中氮茚的电化学硫氰化以及在 DBU 存在下构建 S-P 键的化学过程。循环伏安法和对照实验揭示了该反应的合理 EC 机制。该方法为室温电化学氧化合成-(杂)芳基硫代磷酸酯提供了一条绿色途径，无需外部氧化剂和过渡金属催化剂。
• Controlling chemoselectivity—application of DMF di-t-butyl acetal in the regioselective synthesis of 3-monosubstituted indolizines
  作者：Zhiqiang Xia、Teresa Przewloka、Keizo Koya、Mitsunori Ono、Shoujun Chen、Lijun Sun

  DOI：10.1016/j.tetlet.2006.10.052

  日期：2006.12

  Among a number of DMF dialkyl acetals investigated for the regioselective synthesis of 3-acylindolizines, the di-t-butyl acetal, via its iminium intermediate readily formed in situ, provides the highest chemoselectivity for the intermolecular cyclization of picolinium salts. DMF di-i-butyl acetal was applied to the syntheses of a variety of 3-acylated indolizines including alkyl, aryl, and heteroaryl substituents. (c) 2006 Elsevier Ltd. All rights reserved.