N-<3-(4-Fluorobenzoyl)propyl>-4-piperidone | 39146-45-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-<3-(4-Fluorobenzoyl)propyl>-4-piperidone
• 英文别名: 1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-one；4'-Fluor-4-(4-oxopiperidino)-butyrophenon；1-(4-(4-Fluorophenyl)-4-oxobutyl)piperidin-4-one
• CAS: 39146-45-7
• 化学式: C₁₅H₁₈FNO₂
• mdl: MFCD15483898
• 分子量: 263.312
• InChiKey: BVAUPPRYSPFTLB-UHFFFAOYSA-N

物化性质

• 熔点：
  63 °C
• 沸点：
  415.0±35.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.466
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<3-(4-Fluorobenzoyl)propyl>-4-piperidone 在 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 Spiro(3,4-dihydro-6-chloro-1,2,4-benzotrazine-3,4'-{1'-[3-(4-fluorobenzoyl)propyl]}piperidine)
  参考文献：
  名称：

  Novelli; Sparatore, Il Farmaco, 1996, vol. 51, # 8-9, p. 541 - 550

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯-4'-氟苯丁酮 在 氢溴酸 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 N-<3-(4-Fluorobenzoyl)propyl>-4-piperidone
  参考文献：
  名称：

  Spiro[1,2,4-benzotriazine-3(4H),4′-(1′-substituted)piperidines] and related compounds as ligands for sigma receptors

  摘要：

  As analogues of some conformationally restricted spiropiperidine derivatives which are endowed with high affinity for sigma(1), receptor, a set of 16 spiro[1,2,4-benzotriazine-3(4H),4'-(1'-substituted)piperidines] and congeneric compounds was prepared and tested for affinity to a, receptor subtype. All N-arylalkyl substituted derivatives exhibited high affinity for the relevant receptor, with K-i in the low nanomolar range. Affinity for sigma(2) subtype (assayed only for a few representative compounds) was from one to three order of magnitude lower. Spiro[ 1,2,4-benzotriazine-3(4H),4'-(1'-benzyl)piperidine] (2), with a ratio K(i)sigma(2)/K(j)sigma(1) = 7000 should represent the most selective sigma(1), ligand so far described. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01293-4

文献信息

• Bioisosteric Replacement Leading to Biologically Active [2.2]Paracyclophanes with Altered Binding Profiles for Aminergic G-Protein-Coupled Receptors
  作者：Marika Skultety、Harald Hübner、Stefan Löber、Peter Gmeiner

  DOI：10.1021/jm100899z

  日期：2010.10.14

  Exploring the chemical diversity space of GPCR ligands, we recently discovered [2.2]paracyclophanes as valuable atypical bioisosteres for secondary affinity and selectivity generating moieties. In find out if such an exchange also works for structural moieties that simulate the endogenous neurotransmitter, pi 1 or pi 2 or both systems pi 1 and pi 2 of three representative privileged structures of types 1, 2. and 3 were replaced by a [2.2]paracyclophane unit. Contributions of the respective functionalities to the binding at of a panel of relevant monoaminergic GPCRs were systematically examined. The study led to the paracyclophanylpiperazine 3a displaying excellent D-3 affinity (K-i = 1.6 nM) and a strongly attenuated binding to D-4, 5-HT1 and alpha(1). Whereas functional experiments showed neutral D-3 antagonist properties, mutagenesis studies indicated a binding mode that is similar to its lead compounds of type 3.