1-benzyl-4-<<(4-fluorobenzyl)oxy>methyl>piperidine | 138030-79-2

• 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-benzyl-4-<<(4-fluorobenzyl)oxy>methyl>piperidine
• 英文别名: 1-Benzyl 4-(4'-fluorobenzyloxymethyl)piperidine；1-benzyl-4-[(4-fluorophenyl)methoxymethyl]piperidine
• CAS: 138030-79-2
• 化学式: C₂₀H₂₄FNO
• 分子量: 313.415
• InChiKey: XBBPMZNIRPSONU-UHFFFAOYSA-N

物化性质

• 沸点：
  401.8±25.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-<<(4-fluorobenzyl)oxy>methyl>piperidine 在 氢氧化钾 、 potassium carbonate 作用下， 以 甲醇 、 苯 为溶剂， 反应 60.5h， 生成 4-(4-Fluoro-benzyloxymethyl)-1-pentyl-piperidine; hydrochloride
  参考文献：
  名称：

  Novel piperidine .sigma. receptor ligands as potential antipsychotic drugs

  摘要：

  Sigma receptor ligands represent a new class of potential antipsychotic drugs. This paper presents the structure-activity relationships leading to novel disubstituted piperidine sigma ligands, which have little or no affinity for dopamine D2 receptors. Selectivity for sigma sites over dopamine D2 or serotonin 5-HT2 receptors appears to be governed by the chemical nature of the piperidine nitrogen substituent, its distance from the basic nitrogen, and its orientation relative to the other piperidine substituent. Several of these compounds have good oral potency in some animal models used to evaluate potential antipsychotic drugs. The N-cyclopropylmethyl ketones and ethers (e.g. 6i (DuP 734), 6q, 18a, and 18n) have the best in vivo potency. Compounds 6i (DuP 734) and 6q did not cause catalepsy in the rat, even at very high doses. On the basis of the pharmacology profiles of these sigma ligands, we propose these compounds may be effective antipsychotic drugs, which do not induce extrapyramidal side effects or tardive dyskinesia.

  DOI：

  10.1021/jm00101a012
• 作为产物：
  描述：

  1-苄基-4-哌啶甲酸乙酯 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 92.0h， 生成 1-benzyl-4-<<(4-fluorobenzyl)oxy>methyl>piperidine
  参考文献：
  名称：

  Novel piperidine .sigma. receptor ligands as potential antipsychotic drugs

  摘要：

  Sigma receptor ligands represent a new class of potential antipsychotic drugs. This paper presents the structure-activity relationships leading to novel disubstituted piperidine sigma ligands, which have little or no affinity for dopamine D2 receptors. Selectivity for sigma sites over dopamine D2 or serotonin 5-HT2 receptors appears to be governed by the chemical nature of the piperidine nitrogen substituent, its distance from the basic nitrogen, and its orientation relative to the other piperidine substituent. Several of these compounds have good oral potency in some animal models used to evaluate potential antipsychotic drugs. The N-cyclopropylmethyl ketones and ethers (e.g. 6i (DuP 734), 6q, 18a, and 18n) have the best in vivo potency. Compounds 6i (DuP 734) and 6q did not cause catalepsy in the rat, even at very high doses. On the basis of the pharmacology profiles of these sigma ligands, we propose these compounds may be effective antipsychotic drugs, which do not induce extrapyramidal side effects or tardive dyskinesia.

  DOI：

  10.1021/jm00101a012

文献信息

• Piperidine ether derivatives as psychotropic drugs or plant fungicides
  申请人：Du Pont Merck Pharmaceutical Company

  公开号：US05169855A1

  公开（公告）日：1992-12-08

  There are provided piperidine ether derivatives, pharmaceutical and agricultural compositions containing them useful for treating physiological or drug induced psychosis or dyskinesia in a mammal or fungal disease in plants. Also provided are methods for preparing these compounds.

  提供了哌啶醚衍生物，其中包括用于治疗哺乳动物中的生理或药物诱导的精神病或运动障碍，以及植物真菌病的药物和农业组合物。还提供了制备这些化合物的方法。
• Piperidin ether derivatives as psychotropic drugs or plant fungicides
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0449187A2

  公开（公告）日：1991-10-02

  There are provided piperidine ether derivatives (I) pharmaceutical and agricultural compositions containing them useful for treating physiological or drug induced psychosis or dyskinesia in a mammal or fungal disease in plants. Also provided are methods for preparing these compounds.

  本发明提供了哌啶醚衍生物(I)以及含有哌啶醚衍生物(I)的药物和农用组合物，用于治疗哺乳动物的生理性或药物诱发的精神错乱或运动障碍，或植物的真菌病。还提供了制备这些化合物的方法。
• Novel piperidine .sigma. receptor ligands as potential antipsychotic drugs
  作者：Paul J. Gilligan、Gary A. Cain、Thomas E. Christos、Leonard Cook、Spencer Drummond、Alexander L. Johnson、Ahmed A. Kergaye、John F. McElroy、Kenneth W. Rohrbach

  DOI：10.1021/jm00101a012

  日期：1992.11

  Sigma receptor ligands represent a new class of potential antipsychotic drugs. This paper presents the structure-activity relationships leading to novel disubstituted piperidine sigma ligands, which have little or no affinity for dopamine D2 receptors. Selectivity for sigma sites over dopamine D2 or serotonin 5-HT2 receptors appears to be governed by the chemical nature of the piperidine nitrogen substituent, its distance from the basic nitrogen, and its orientation relative to the other piperidine substituent. Several of these compounds have good oral potency in some animal models used to evaluate potential antipsychotic drugs. The N-cyclopropylmethyl ketones and ethers (e.g. 6i (DuP 734), 6q, 18a, and 18n) have the best in vivo potency. Compounds 6i (DuP 734) and 6q did not cause catalepsy in the rat, even at very high doses. On the basis of the pharmacology profiles of these sigma ligands, we propose these compounds may be effective antipsychotic drugs, which do not induce extrapyramidal side effects or tardive dyskinesia.