4-Benzyl-1-(4-p-fluorophenyl-4,4-ethylendioxy)butylpiperidine | 153208-89-0

• 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: 4-Benzyl-1-(4-p-fluorophenyl-4,4-ethylendioxy)butylpiperidine
• 英文别名: 4-Benzyl-1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidine
• CAS: 153208-89-0
• 化学式: C₂₄H₃₀FNO₂
• 分子量: 383.506
• InChiKey: ULWVRIYFAVHKLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Benzyl-1-(4-p-fluorophenyl-4,4-ethylendioxy)butylpiperidine 在 盐酸 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 4-(4-Benzylpiperidin-1-yl)-1-(4-fluorophenyl)butan-1-ol
  参考文献：
  名称：

  7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics

  摘要：

  Compound 1 (1-benzyl-3-methyl-4-[4-(4-fluorophenyl)- a synthetic intermediate identified as a potential atypical antipsychotic, was selected as the starting point for pharmacological improvement. From 1, sequential structural variations were conducted in order to improve its potency and oral bioavailability. These variations included a series of piperazine, ethanediamine, and piperidine derivatives. The piperidine series afforded some orally potent compounds in the inhibition of apomorphine-induced climbing and hyperactivity in mice, which are regarded as behavioral models predictive of antipsychotic efficacy. Further optimization of these structures led to the highly potent 7-[3-(1-piperidinyl)propoxy]chromenones. Inhibition of stereotypies and induction of catalepsy in rats at doses substantially higher than required for inhibition of climbing suggest an atypical antipsychotic profile, which is assumed to predict a reduced induction of extrapyramidal side effects in humans.

  DOI：

  10.1021/jm950894b
• 作为产物：
  描述：

  4-苄基哌啶 、 2-(3-氯丙基)-2-(4-氟苯基)-1,3-二氧戊烷 在 potassium iodide 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 以20 g (91%)的产率得到4-Benzyl-1-(4-p-fluorophenyl-4,4-ethylendioxy)butylpiperidine
  参考文献：
  名称：

  4-benzylpiperidines for treating phychosis

  摘要：

  4-苄基哌啶衍生物的化学式为：##STR1## 或其药用可接受的酸盐，其中X为氢或氟，R为氢，或者从对氟苯甲酰、α-羟基-对氟苯甲基、对氟苯氧基、双(对氟苯基)甲基和8-氮杂螺[4,5]癸烷-7,9-二酮-8-基甲基中选择的基团，但X和R不能同时为氢和对氟苯甲酰。这些化合物可用作sigma受体配体。

  公开号：

  US05395841A1

文献信息

• 4-benzylpiperidines for treating phychosis
  申请人：Ferrer Internacional, S.A.

  公开号：US05395841A1

  公开（公告）日：1995-03-07

  4-Benzylpiperidine derivatives of the formula: ##STR1## or a pharmaceutically acceptable acid addition salt thereof, wherein X is hydrogen or fluorine and R is hydrogen, or a group selected from p-fluorobenzoyl, .alpha.-hydroxy-p-fluorobenzyl, p-fluorophenoxy, bis(p-fluorophenyl)methyl and 8-azaspiro[4,5]decane-7,9-dione-8-yl-methyl, with the proviso that X and R may not be simultaneously hydrogen and p-fluorobenzoyl respectively. Such compounds are useful as sigma-receptor ligands.

  4-苄基哌啶衍生物的化学式为：##STR1## 或其药用可接受的酸盐，其中X为氢或氟，R为氢，或者从对氟苯甲酰、α-羟基-对氟苯甲基、对氟苯氧基、双(对氟苯基)甲基和8-氮杂螺[4,5]癸烷-7,9-二酮-8-基甲基中选择的基团，但X和R不能同时为氢和对氟苯甲酰。这些化合物可用作sigma受体配体。
• 4-Benzylpiperidine derivatives, a process for preparing them and pharmaceutical compositions containing them
  申请人：FERRER INTERNACIONAL, S.A.

  公开号：EP0572952A1

  公开（公告）日：1993-12-08

  4-Benzylpiperidine derivatives of the formula: or a pharmaceutically accpetable acid addition salt thereof, wherein X is hydrogen or fluorine and R is hydrogen, or a group selected from p-fluorobenzoyl, alpha-hydroxy-p-fluorobenzyl, p-fluorophenoxy, bis(p-fluorophenyl)methyl and 8-azaspiro [4,5] decane-7,9-dione-8-yl-methyl with the proviso that X and R may not be simultaneously hydrogen and p-fluorobenzoyl respectively. Such compounds are useful as sigma-receptor ligands.

  式中的 4-苄基哌啶衍生物： 或其可药用的酸加成盐，其中 X 为氢或氟，R 为氢或选自对氟苯甲酰基、α-羟基-对氟苄基、对氟苯氧基、双（对氟苯基）甲基和 8-氮杂螺[4,5]癸烷-7,9-二酮-8-基-甲基的基团，但 X 和 R 不得分别同时为氢和对氟苯甲酰基。 此类化合物可用作σ受体配体。
• US5395841A
  申请人：——

  公开号：US5395841A

  公开（公告）日：1995-03-07
• 7-[3-(1-Piperidinyl)propoxy]chromenones as Potential Atypical Antipsychotics
  作者：Jordi Bolós、Santiago Gubert、Lluís Anglada、Josep M. Planas、Carme Burgarolas、Josep M. Castelló、Aurelio Sacristán、José A. Ortiz

  DOI：10.1021/jm950894b

  日期：1996.1.1

  Compound 1 (1-benzyl-3-methyl-4-[4-(4-fluorophenyl)- a synthetic intermediate identified as a potential atypical antipsychotic, was selected as the starting point for pharmacological improvement. From 1, sequential structural variations were conducted in order to improve its potency and oral bioavailability. These variations included a series of piperazine, ethanediamine, and piperidine derivatives. The piperidine series afforded some orally potent compounds in the inhibition of apomorphine-induced climbing and hyperactivity in mice, which are regarded as behavioral models predictive of antipsychotic efficacy. Further optimization of these structures led to the highly potent 7-[3-(1-piperidinyl)propoxy]chromenones. Inhibition of stereotypies and induction of catalepsy in rats at doses substantially higher than required for inhibition of climbing suggest an atypical antipsychotic profile, which is assumed to predict a reduced induction of extrapyramidal side effects in humans.