1-benzyl-3-methoxycarbonyl-pyridinium; chloride | 7146-29-4

• 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-benzyl-3-methoxycarbonyl-pyridinium; chloride
• 英文别名: 1-Benzyl-3-methoxycarbonyl-pyridinium; Chlorid；Nicotinsaeure-methylester-benzylochlorid；Methyl 1-benzylpyridin-1-ium-3-carboxylate;chloride
• CAS: 7146-29-4
• 化学式: C₁₄H₁₄NO₂*Cl
• 分子量: 263.724
• InChiKey: HWOFJZFPVUAMIA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.19
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1-benzyl-3-methoxycarbonyl-pyridinium; chloride 在 palladium on activated charcoal sodium tetrahydroborate 、 3 Angstroem MS 、 氢气 、 溴 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 生成 1-Benzyl-2-(benzylamino-methyl)-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Pyrrolidines bearing a quaternary α-stereogenic center. Part 2: Access to proline chimeras, stereoselective approach and mechanistic aspects

  摘要：

  The present work describes the access to various proline chimeras bearing a quaternary cx-stereogenic center, via the Duhamel ring contraction of heterocyclic enamines. Attempts to induce diastereoselectivity are reported. The 'chiral enamine' strategy afforded the required aminoaldehydes with diastereomeric ratios as high as 85:15. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00505-0
• 作为产物：
  描述：

  烟酸甲酯 在 silver(I) chloride 作用下， 以 甲醇 为溶剂， 生成 1-benzyl-3-methoxycarbonyl-pyridinium; chloride
  参考文献：
  名称：

  Pyrrolidines bearing a quaternary α-stereogenic center. Part 2: Access to proline chimeras, stereoselective approach and mechanistic aspects

  摘要：

  The present work describes the access to various proline chimeras bearing a quaternary cx-stereogenic center, via the Duhamel ring contraction of heterocyclic enamines. Attempts to induce diastereoselectivity are reported. The 'chiral enamine' strategy afforded the required aminoaldehydes with diastereomeric ratios as high as 85:15. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00505-0

文献信息

• Synthesis of 3,5-diacyl-4-phenyl-1,4-dihydropyridines
  作者：M.-Lluïsa Bennasar、Cecília Juan、Joan Bosch

  DOI：10.1016/s0040-4039(98)02084-x

  日期：1998.12

  via a regio- and chemoselective addition of Ph2Cu(CN)Li2 to β-substituted N-alkylpyridinium salts, followed by acylation of the intermediate 1,4-dihydropyridines with trichloroacetic anhydride and subsequent haloform-type reaction. A similar sequence using an N-silylpyridinium salt and PhMgBr allows the preparation of the corresponding N-unsubstituted dihydropyridines.

  3,5-二酰基-4-苯基-1,4-二氢吡啶是通过将Ph 2 Cu（CN）Li 2的区域和化学选择性加成到β-取代的N-烷基吡啶鎓盐中，然后将中间体1酰化而合成的，4-二氢吡啶与三氯乙酸酐和随后的卤仿型反应。使用N-甲硅烷基吡啶鎓盐和PhMgBr的相似序列使得可以制备相应的N-未取代的二氢吡啶。
• Biological Evaluation of Bishydroxymethyl-Substituted Cage Dimeric 1,4-Dihydropyridines as a Novel Class of P-Glycoprotein Modulating Agents in Cancer Cells
  作者：Martin Richter、Jósef Molnár、Andreas Hilgeroth

  DOI：10.1021/jm058046w

  日期：2006.5.1

  A series of N-substituted cage dimeric 1,4-dihydropyridines 3a-e was evaluated as inhibitors of membrane efflux pump P-glycoprotein (P-gp) in multidrug resistant (mdr) cancer cells. Structure-activity relationships (SAR) and cytotoxic properties are discussed. Effective concentrations for overcoming mdr have been demonstrated in competition studies with the P-gp substrate epirubicin.
• The First Functionalized 6,12-Diazatetrakishomocubanes
  作者：Andreas Hilgeroth、Ute Baumeister

  DOI：10.1002/(sici)1521-3773(20000204)39:3<576::aid-anie576>3.0.co;2-g

  日期：2000.2.4

  The photodimerization of asymmetric 4-aryl-1,4-dihydropyridines results, totally unexpectedly, in the new 6,12-diazatetrakishomocubanes 1. This is in contrast to the previously observed [2+2] photocycloaddition reactions of symmetrical 4-aryl-1,4-dihydropyridines
• A Study of the Primary Acid Reaction on Model Compounds of Reduced Diphosphopyridine Nucleotide^1,2
  作者：Arthur G. Anderson、Gerald Berkelhammer

  DOI：10.1021/ja01537a063

  日期：1958.2
• Pyrrolidines bearing a quaternary α-stereogenic center. Part 2: Access to proline chimeras, stereoselective approach and mechanistic aspects
  作者：Delphine Trancard、Jean-Baptiste Tout、Thierry Giard、Ilhame Chichaoui、Dominique Cahard、Jean-Christophe Plaquevent

  DOI：10.1016/s0040-4039(00)00505-0

  日期：2000.5

  The present work describes the access to various proline chimeras bearing a quaternary cx-stereogenic center, via the Duhamel ring contraction of heterocyclic enamines. Attempts to induce diastereoselectivity are reported. The 'chiral enamine' strategy afforded the required aminoaldehydes with diastereomeric ratios as high as 85:15. (C) 2000 Elsevier Science Ltd. All rights reserved.