1-(4'-fluorobenzyl)pyridinium chloride | 473535-50-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4'-fluorobenzyl)pyridinium chloride
• 英文别名: 4-Fluoro-benzylpyridinium chloride；1-[(4-fluorophenyl)methyl]pyridin-1-ium;chloride
• CAS: 473535-50-1
• 化学式: C₁₂H₁₁FN*Cl
• 分子量: 223.677
• InChiKey: STZAEEAFKDUSOD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4'-fluorobenzyl)pyridinium chloride 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 26.42h， 生成 (3SR,4SR)-1-(4-fluorobenzyl)-3-(4-phenylpiperidin-1-yl)piperidin-4-ol
  参考文献：
  名称：

  High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4-epoxypiperidines with amines—a short-step synthesis of 4-fluorobenzyltrozamicol and novel anilidopiperidines

  摘要：

  Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxypiperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, 4-fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new beta-hydroxy substituted anilidopiperidines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.045
• 作为产物：
  描述：

  吡啶 、 4-氟氯苄 反应 25.0h， 生成 1-(4'-fluorobenzyl)pyridinium chloride
  参考文献：
  名称：

  High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4-epoxypiperidines with amines—a short-step synthesis of 4-fluorobenzyltrozamicol and novel anilidopiperidines

  摘要：

  Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxypiperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, 4-fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new beta-hydroxy substituted anilidopiperidines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.045

文献信息

• Peculiar magnetic behavior in ion-pair complex [1-(4′-fluorobenzyl)pyridinium][Ni(mnt)₂] (mnt²⁻= maleonitriledithiolate)
  作者：Jingli Xie、Xiaoming Ren、You Song、Wenwei Zhang、Wenlong Liu、Cheng He、Qingjin Meng

  DOI：10.1039/b205441h

  日期：——

  An ion-pair complex [FBzPy][Ni(mnt)2], where [FBzPy]+ = 1-(4′-fluorobenzyl)pyridinium and mnt2− = maleonitriledithiolate, forms a discrete stacking column and shows a peculiar magnetic transition from paramagnetic to diamagnetic around 90 K.

  离子对复合物[FBzPy][Ni(mnt)2]（其中[FBzPy]+ = 1-（4â²-氟苄基）吡啶鎓，mnt2â = 马来酰亚胺二硫酸盐）形成了一个离散的堆积柱，并在 90 K 左右出现了从顺磁性到二磁性的奇特磁性转变。
• New ion-pair nickel(III) complexes containing [Ni(‘S2’)2] (‘S2’2−=1,2-benzenedithiolate) fragments: synthesis, crystal structure and properties
  作者：Jing-Li Xie、Xiao-Ming Ren、Cheng He、You Song、Chun-Yin Duan、Song Gao、Qing-Jin Meng

  DOI：10.1016/s0277-5387(02)01334-7

  日期：2003.1

  Two new ion-pair complexes [1-(4'-fluorobenzyl)pyridinium][Ni(bdt)(2)] (1) and [1-(4'-bromobenzyl)pyridinium][Ni(bdt)(2)] (2), in which bdt(2-) = 1,2-benzenedithiolate ('S-2(,2-)), have been prepared and characterized. X-ray structural analyses showed that 1 and 2 are isostructural, and the anions are centrosymmetric. The 2 non-equiv. anions form different uniform-spaced stacking pattern in I and 2. The magnetic measurements of 1 and 2 indicate ferromagnetic behavior in the antiferromagnetic exchange system, which may arise from spin canting. Cyclovoltammetry revealed two quasi-reversible one-electron steps for I and 2, which are attributed to Ni(IV/III) and Ni(III/II) redox couples. (C) 2002 Elsevier Science Ltd. All rights reserved.
• High regiocontrol in the nucleophilic ring opening of 1-aralkyl-3,4-epoxypiperidines with amines—a short-step synthesis of 4-fluorobenzyltrozamicol and novel anilidopiperidines
  作者：Matthias Scheunemann、Lothar Hennig、Uta Funke、Jörg Steinbach

  DOI：10.1016/j.tet.2011.03.045

  日期：2011.5

  Nucleophilic ring-opening reactions of three 1-aralkyl-3,4-epoxypiperidines with a series of aliphatic and aromatic amines have been investigated. Reactions in protic solvents, preferably 2-propanol, gave rise to 3-amino-piperidin-4-ols in ratios up to 20:1. Accordingly, 4-fluorobenzyltrozamicol, a highly potent ligand for the vesicular acetylcholine transporter was obtained directly from an epoxide ring opening in one step, without the need of chromatographic separation. Reactions in acetonitrile assisted by Li-salts, most suitable with LiBr, led regioselectively to trans-4-amino-piperidin-3-ols in high yields. N-Phenethyl substituted anilino-piperidinols as easily obtained by this method were converted into a series of new beta-hydroxy substituted anilidopiperidines. (C) 2011 Elsevier Ltd. All rights reserved.