1-phenethyl-4-hydroxy-4-(4-methoxyphenyl)piperidinium hydrochloride | 1174916-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-phenethyl-4-hydroxy-4-(4-methoxyphenyl)piperidinium hydrochloride
• 英文别名: 1-phenethyl-4-hydroxy-4-(4-methoxyphenyl)piperidinium chloride
• CAS: 1174916-47-2
• 化学式: C₂₀H₂₅NO₂*ClH
• 分子量: 347.885
• InChiKey: RPGWRAGWKSJNIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-溴苯甲醚 、 N-(2-苯乙基)-4-哌啶酮 在 碘 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 以60.1%的产率得到1-phenethyl-4-hydroxy-4-(4-methoxyphenyl)piperidinium hydrochloride
  参考文献：
  名称：

  Synthesis and anti-leukemia activity mensuration of 1-phenethyl-4-hydroxy-4-substituted piperidinium hydrochlorides: Structure of bis[1-phenethyl-4-hydroxy-4-(3-fluorophenyl) piperidinium hydrochloride] studied by X-ray and DFT methods

  摘要：

  Four unknown compounds have been synthesized based on the molecular motif of 1-phenethyl-4-hydroxy piperidinium hydrochloride with a variety of the substituted groups R on the same carbon atom bearing the hydroxy group, such as 3-fluorophenyl (3a), 4-methoxyphenyl (3b), 4-methylphenyl (3c) and cyclohexanyl (3d), and their molecular structures were characterized by H-1 NMR, MS and IR. To account for the stereo structure and provide more information on the effect of counter ions, hydrogen bonds on molecular conformation, the structure of [1-phenethyl-4-hydroxy-4-(3-fluorophenyl) piperidinium hydrochloride] [PHFPH center dot Cl] 3a was determined by the single-crystal X-ray analysis and optimized by the B3LYP/6-31G (d, p) calculations. Two chloride anions, two PHFPH cations and a dichloromethane molecule formed a five-membered structure ([(PHFPH)(2)Cl-2]center dot CH2Cl2) via the intermolecular hydrogen bonds. The core of the five-membered structure ([(PHFPH)(2)Cl-2]center dot CH2Cl2) is formed by two PHFPH cations linked by N(1B)-H(2)center dot center dot center dot Cl(2) hydrogen bonds of lengths 3.033(4), which is engaged in two hydrogen bonds: N(1A)-H(1)center dot center dot center dot Cl(1) of 3.110(4) angstrom and O(1B)-H(2B)center dot center dot center dot Cl(1) of 3.099(4) angstrom. The anti-tumor activity tests indicated that these Compounds Could inhibit the growth of the K562 cells to some extent and have the potential bioactivity of anti-leukemia. (c) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2009.04.008