1-(phenylmethyl)-4-piperidinecarboxylic acid ethyl ester hydrochloride | 111627-24-8

• 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-(phenylmethyl)-4-piperidinecarboxylic acid ethyl ester hydrochloride
• 英文别名: 1-(Phenylmethyl)-4-piperidinecarboxylic acid ethyl ester hydrochloride[1:1]；(1-benzylpiperidin-4-yl) ethylcarboxylate hydrochloride；(1-benzylpiperidin-4-yl)ethylcarboxylate hydrochloride；ethyl 1-benzylpiperidine-4-carboxylate;hydrochloride
• CAS: 111627-24-8
• 化学式: C₁₅H₂₁NO₂*ClH
• 分子量: 283.798
• InChiKey: BPSWFJWNZKIQFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(phenylmethyl)-4-piperidinecarboxylic acid ethyl ester hydrochloride 在 lithium aluminium tetrahydride 、 sodium hydroxide 、 水 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 4.0h， 以85.6%的产率得到1-苄基-4-哌啶甲醇
  参考文献：
  名称：

  WO2007/7072

  摘要：

  公开号：
• 作为产物：
  描述：

  1-苄基-4-哌啶甲酸乙酯 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 1-(phenylmethyl)-4-piperidinecarboxylic acid ethyl ester hydrochloride
  参考文献：
  名称：

  WO2007/7072

  摘要：

  公开号：

文献信息

• Synthesis and antiallergy activity of 4-(diarylhydroxymethyl)-1-[3-(aryloxy)propyl)piperidines and structurally related compounds
  作者：David A. Walsh、Stephen K. Franzyshen、John M. Yanni

  DOI：10.1021/jm00121a022

  日期：1989.1

  A series of 4-(diarylhydroxymethyl)-1-[3-(aryloxy)propyl]piperidines was synthesized and evaluated for antiallergy activity. Several analogues had potent activity in the passive foot anaphylaxis (PFA) assay, an IgE-mediated model useful in the detection of compounds possessing antiallergic activity. In particular 1-[4-[3-[4-[bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl] propoxy]-3-methoxyphenyl]ethanone

  合成了一系列的4-（二芳基羟甲基）-1- [3-（芳氧基）丙基]哌啶，并评估了其抗过敏活性。几种类似物在被动足过敏症（PFA）检测中具有有效活性，PFA检测是一种IgE介导的模型，可用于检测具有抗过敏活性的化合物。特别是1- [4- [3- [4- [双（4-氟苯基）羟甲基] -1-哌啶基]丙氧基] -3-甲氧基苯基]乙酮（1，AHR-5333）比奥沙米特和特非那定在这种测定。
• Synthesis and preliminary pharmacological results on new naphthalene derivatives as 5-HT4 receptor ligands
  作者：Ousmane Diouf、Patrick Depreux、Philippe Chavatte、Jacques Henri Poupaert

  DOI：10.1016/s0223-5234(00)00163-x

  日期：2000.8

  reference ligand for labelling the 5-HT(4) serotoninergic receptors. Previous works in our laboratories established the bioisosteric equivalency of the indole heterocycle and naphthalene in a series of melatonin receptor ligands. Based on this knowledge we designed new analogues of GR 113808 by introducing two bioisosteric modifications: firstly, the indole ring was replaced by a naphthalene one and

  吲哚衍生物GR 113808当前用作标记5-HT（4）5-羟色胺能受体的参考配体。我们实验室中以前的工作建立了一系列褪黑激素受体配体中吲哚杂环和萘的生物等位当量。基于这一知识，我们通过引入两个生物等位变体设计了GR 113808的新类似物：首先，吲哚环被萘取代，其次，酯键被酰胺基取代。化合物8出现在这个新系列中，因为它在5-HT（4）受体上显示出高选择性的亲和力（Ki 5-HT（4）= 6 nM，Ki 5-HT（3）= 100 nM，在其他5个处的Ki值-HT受体高于1000 nM。化合物8目前正在进行进一步的药理评估。
• Arylalkylheterocyclic amines,N-substituted by aryloxyalkyl group in a
  申请人：A. H. Robins Company, Incorporated

  公开号：US04950674A1

  公开（公告）日：1990-08-21

  A method of inhibiting Type 1 allergic responses in a living animal body with substituted heterocyclic amines is disclosed wherein the active agents are expressed generally by the formula which includes certain known and certain known compounds: ##STR1## wherein P is zero, one or two; m is one to six inclusive; A is selected from hydrogen, hydroxy or cyano; d is zero or one; Q is --CH--, CH.sub.2 -- or ##STR2## n is zero or one and when Q is --CH-- and n is one, a double bond is formed with one of the adjacent carbons but not both at the same time, and when n and d are zero at the same time, a double bond is formed between the .alpha. carbon and a carbon of the central heterocyclic amine ring; Ar, D and R are selected from phenyl, substituted phenyl, pyridinyl, thienyl, furanyl or naphthyl and in addition, R may have the values benzyl, substituted benzyl, cycloalkyl or loweralkyl and D may additionally have the values: 2H-1-benzopyran-2-one,4-oxo-4H-1-benzopyran-2-carboxylic acid loweralkyl ester, 2,3-dihydro-4H-1-benzopyran-4-one, 1,4-benzodioxanloweralkyl-2-yl or 1,1'-biphenyl-4-yl and the pharmaceutically acceptable salts thereof.

  公开了一种使用取代杂环胺抑制活体动物体内1型过敏反应的方法，其中活性剂通常由以下公式表示，其中包括某些已知化合物和某些已知化合物：##STR1##其中P为零、一或二；m为1至6的整数；A选自氢、羟基或氰基；d为零或一；Q为--CH--、CH.sub.2--或##STR2##n为零或一，当Q为--CH--且n为一时，会与相邻碳之一形成双键，但不会同时与两个形成双键；当n和d同时为零时，会在α碳和中心杂环胺环的碳之间形成双键；Ar、D和R选自苯基、取代苯基、吡啶基、噻吩基、呋喃基或萘基，并且此外，R可以具有苄基、取代苄基、环烷基或较低烷基的值，D还可以具有以下值：2H-1-苯并吡喃-2-酮、4-氧代-4H-1-苯并吡喃-2-羧酸较低烷基酯、2,3-二氢-4H-1-苯并吡喃-4-酮、1,4-苯并二氧杂环较低烷基-2-基或1,1'-联苯-4-基及其药学上可接受的盐。
• Arylalkyl-heterocyclic amines, n-substituted by aryloxyalkyl groups used
  申请人：A. H. Robins Company, Incorporated

  公开号：US04810713A1

  公开（公告）日：1989-03-07

  A method of treating allergy with substituted heterocyclic amines is disclosed wherein the active agents are expressed generally by the formula which includes certain known and certain novel compounds: ##STR1## wherein p is zero, one or two; m is one to six inclusive; A is selected from hydrogen, hydroxy or cyano; d is zero or one; Q is --CH--, --CH.sub.2 -- or ##STR2## n is zero or one and when Q is --CH-- and n is one, a double bond is formed with one of the adjacent carbons but not both at the same time, and when n and d are zero at the same time, a double bond is formed between the .alpha. carbon and a carbon of the central heterocyclic amine ring; Ar, D and R are selected from phenyl, substituted phenyl, pyridinyl, thienyl, furanyl or naphthyl and in addition, R may have the values benzyl, substituted benzyl, cycloalkyl or loweralkyl and D may additionally have the values: 2H-1-benzopyran-2-one, 4-oxo-4H-1-benzopyran-2-carboxylic acid loweralkyl ester, 2,3-dihydro-4H-1-benzopyran-4-one or 1,4-benzodioxan-loweralkyl-2-yl, and the pharmaceutically acceptable salts thereof.

  本发明涉及一种使用取代杂环胺治疗过敏的方法，其中活性剂通常由以下公式表示，包括某些已知和某些新化合物：##STR1## 其中p为零、一或二；m为一到六之间；A选自氢、羟基或氰基；d为零或一；Q为--CH--、--CH.sub.2--或##STR2## n为零或一，当Q为--CH--且n为一时，与相邻的碳原子之一形成双键，但不能同时与两个碳原子形成双键；当n和d同时为零时，与中心杂环胺环的碳原子之一形成双键；Ar、D和R选自苯基、取代苯基、吡啶基、噻吩基、呋喃基或萘基，此外，R可能为苄基、取代苄基、环烷基或低碳基，D还可能具有以下值：2H-1-苯并吡喃-2-酮、4-氧代-4H-1-苯并吡喃-2-羧酸低碳酸酯、2,3-二氢-4H-1-苯并吡喃-4-酮或1,4-苯并二氧杂环低碳基-2-基，并且其药学上可接受的盐。
• Aryl(alkyland alkylene)-N-((phenoxy and phenylthio)alkyl)
  申请人：A. H. Robins Company, Incorporated

  公开号：US05070087A1

  公开（公告）日：1991-12-03

  A method of treating cardiac dysfunction, the effects of histamine, and gastric secretion excesses with aryl(alkyl and alkylene)-N-[(phenoxy and phenythio)alkyl]aminoheterocyclics corresponding to the formula: ##STR1## wherein Ar is phenyl or substituted phenyl; R is phenyl, substituted phenyl, pyridinyl or cycloalkyl; A is hydrogen, hydroxy, cyano, amido and amino; Q is --CH.sub.2 --, --CH--, or --CHOH--; d and n are zero or one and the dotted lines form double bonds consistent with the valence of carbon; p is zero, one or two; m is one to six inclusive; B is oxygen, nitrogen, sulfur, sulfinyl or sulfonyl; z is zero or one; l is zero or one; W is hydrogen, loweralkyl, halo, nitro, loweralkoxy or hydroxy; X is hydrogen, loweralkyl, halogen, loweralkoxy or hydroxy; Y is --CH(OH)CH.sub.2 OH, --CH(OH)C(O)OH, --C(O)C(O)OH, --C(O)CH.sub.2 OH,--C(O)C(O)OCH.sub.3, --C(O)C(O)OC.sub.2 H.sub.5, --CH.sub.2 C(O)OC.sub.2 H.sub.5, --CH(OH)C(O)OCH.sub.3, --CH(OH)C(O)OC.sub.2 H.sub.5 or --C(O)CH.sub.2 OC(O)CH.sub.3 ; and the pharmaceutically acceptable salts thereof; in addition to the above methods of treatment, compounds wherein (B).sub.z is oxygen are useful in a method of treating Gell and Coombs type 1 allergic responses in mammals.

  一种用芳基（烷基和烷基烯）-N- [（苯氧基和苯硫基）烷基]氨基杂环化合物治疗心脏功能障碍，组胺和胃分泌过多的方法，该化合物对应于以下公式：##STR1## 其中Ar是苯或取代苯基; R是苯基，取代苯基，吡啶基或环烷基; A是氢，羟基，氰基，酰胺基和氨基; Q是--CH.sub.2 --，--CH--或--CHOH--; d和n为零或一，虚线形成与碳的价相一致的双键; p为零，一或二; m为1至6包括在内; B是氧，氮，硫，亚砜或磺酰基; z为零或一; l为零或一; W是氢，低烷基，卤素，硝基，低烷氧基或羟基; X是氢，低烷基，卤素，低烷氧基或羟基; Y是--CH（OH）CH.sub.2 OH，--CH（OH）C（O）OH，--C（O）C（O）OH，--C（O）CH.sub.2 OH，--C（O）C（O）OCH.sub.3，--C（O）C（O）OC.sub.2 H.sub.5，--CH.sub.2 C（O）OC.sub.2 H.sub.5，--CH（OH）C（O）OCH.sub.3，--CH（OH）C（O）OC.sub.2 H.sub.5或--C（O）CH.sub.2OC（O）CH.sub.3;以及其药学上可接受的盐; 除了上述治疗方法外，当（B）.sub.z为氧时，化合物对哺乳动物的Gell和Coombs 1型过敏反应的治疗方法也有用。