N-环己基甲基-4-哌啶酮 | 64306-76-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: N-环己基甲基-4-哌啶酮
• 英文名称: 1-(cyclohexylmethyl)piperidin-4-one
• 英文别名: 1-cyclohexylmethylpiperid-4-one
• CAS: 64306-76-9
• 化学式: C₁₂H₂₁NO
• mdl: MFCD09947739
• 分子量: 195.305
• InChiKey: NDBCDBUOZCCWQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.916
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-环己基甲基-4-哌啶酮 在 aluminum nickel 盐酸 、 sodium hydroxide 、 氨 作用下， 生成 1-(环己基甲基)哌啶-4-胺
  参考文献：
  名称：

  Anti-psychotic (cycloalkenylalkylpiperidino) benzamides

  摘要：

  这项发明涉及哌啶衍生物。更具体地说，该发明涉及N-取代哌啶的取代苯甲酸酰胺及其药物组合物，该组合物在拮抗内源或外源多巴胺或多巴胺能药物的作用方面具有用途，并用于治疗由胃肠道紊乱、充血性心力衰竭、术后情况等引起的恶心和呕吐，以及其他胃肠道紊乱，如消化不良、胀气、胆汁逆流、食管裂孔疝、消化性溃疡、反流性胃气胀、胃炎、十二指肠炎和胆结石等，并用于治疗影响中枢神经系统的多种疾病，如急性和慢性精神病、狂躁精神病、精神分裂症、严重的行为紊乱和非忧郁性抑郁状态以及偏头痛。该发明还涉及制备哌啶衍生物的方法。

  公开号：

  US04163789A1
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 、 溴甲基环己烷 在 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 19.0h， 以47%的产率得到N-环己基甲基-4-哌啶酮
  参考文献：
  名称：

  Synthesis, pharmacological activity and structure affinity relationships of spirocyclic σ1 receptor ligands with a (2-fluoroethyl) residue in 3-position

  摘要：

  In order to develop a fluorinated radiotracer for imaging of sigma(1) receptors in the central nervous system a series of (2-fluoroethyl) substituted spirocyclic piperidines 3 has been prepared. In the key step of the synthesis 2-bromocinnamaldehyde acetal 5 was added to piperidones 6 with various substituents at the N-atom. Unexpectedly, this reaction led to 2-benzoxepines 8, which were contracted with acid to afford the spirocyclic 2-benzofuranacetaldehydes 9. The best yields were obtained, when the transformations up to the alcohols 10 were performed without isolation of intermediates. Generally the (2-fluoroethyl) derivatives 3 have higher sigma(1) affinity and sigma(1)/sigma(2) selectivity than the corresponding (3-fluoropropyl) derivatives 2. The most promising candidate for the development as radiotracer is the (2-fluoroethyl) derivative 3a (WMS-1828, fluspidine, 1'-benzyl-3-(2-fluoroethyl)-3H-spiro[[2]benzofuran-1,4'-piperidine]), which shows subnanomolar sigma(1) affinity (K-i = 0.59 nM) and excellent selectivity over the sigma(2) subtype (1331-fold) as well as some other receptor systems. The novel synthetic strategy also allows the systematic pharmacological evaluation of intermediate alcohols 10. Despite their high sigma(1) affinity (K-i = 6-32 nM) and selectivity the alcohols 10 are 10-30-fold less potent than the bioisosteric fluoro derivatives 3. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.013

文献信息

• Synthesis and structure-activity relationship of spiro[isochromanpiperidine] analogs for inhibition of histamine release. 1
  作者：Masatoshi Yamato、Kuniko Hashigaki、Masao Ikeda、Hidetoshi Ohtake、Kenji Tasaka

  DOI：10.1021/jm00134a013

  日期：1981.2

  ,4'-piperidines] were prepared and examined for their biological activity. Several of the compounds inhibited the compound 48/80 induced histamine release from isolated rat peritoneal mast cells. The structural requirements for this activity in the present series are discussed.

  制备了两种类型的1'-烷基螺基[isochroman-3,4-哌啶]和1'-烷基螺基[isochroman-4,4'-哌啶]并检查了它们的生物学活性。几种化合物抑制了化合物48/80诱导的组胺从分离的大鼠腹膜肥大细胞中释放。讨论了本系列中此活动的结构要求。
• 5-HT
  申请人：山东绿叶制药有限公司

  公开号：CN114728933B

  公开（公告）日：2023-06-16

  本发明涉及一种作为5‑HT2A受体抑制剂或反向激动剂的新化合物及其制备方法和药物组合物。还涉及含有所述化合物或药物组合物在制备治疗5‑HT2A受体相关疾病的药物中的应用，所述疾病包括帕金森病引起的非运动症状：妄想、幻觉、抑郁、焦虑、认知障碍、睡眠障碍；痴呆相关的精神疾病；重度抑郁症；或精神分裂的阴性症状等。
• spiro[piperidine-4,4'-thieno[3,2-c]pyran] derivatives and related compounds as inhibitors of the sigma receptor for the treatment of psychosis
  申请人：Laboratorios del Dr. Esteve S.A.

  公开号：EP2020414A1

  公开（公告）日：2009-02-04

  The present invention relates to compounds having pharmacological activity towards the sigma (σ) receptor, and more particularly to some thieno-pyrano-pyrazole derivatives, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy and prophylaxis, in particular for the treatment of psychosis or pain.

  本发明涉及对 sigma（σ）受体具有药理活性的化合物，特别是一些噻吩并吡喃并吡唑衍生物，涉及此类化合物的制备工艺，涉及包含这些化合物的药物组合物，还涉及它们在治疗和预防中的用途，特别是用于治疗精神病或疼痛。
• Novel non-peptidic neuropeptide Y Y 2 receptor antagonists
  作者：Jill A. Jablonowski、Wenying Chai、Xiaobing Li、Dale A. Rudolph、William V. Murray、Mark A. Youngman、Scott L. Dax、Diane Nepomuceno、Pascal Bonaventure、Timothy W. Lovenberg、Nicholas I. Carruthers

  DOI：10.1016/j.bmcl.2003.12.057

  日期：2004.3

  Through SAR studies of a piperidinylindoline cinnamide HTS lead, the first potent, non-peptide, low molecular weight selective Neuropeptide Y Y-2 (NPY Y-2) antagonists have been synthesized. The SAR studies around the piperidinyl, the indolinyl, and the cinnamyl moieties are discussed. (C) 2003 Elsevier Ltd. All rights reserved.
• Thiophene Bioisosteres of Spirocyclic σ Receptor Ligands. 1. N-Substituted Spiro[piperidine-4,4′-thieno[3,2-<i>c</i>]pyrans]
  作者：Christoph Oberdorf、Dirk Schepmann、Jose Miguel Vela、Jose Luis Diaz、Jörg Holenz、Bernhard Wünsch

  DOI：10.1021/jm8007739

  日期：2008.10.23

  Herein, the synthesis and pharmacological evaluation of thiophene bioisosteres of the highly potent spirocyclic benzopyran 1 are detailed. The synthesis of 1-benzyl-6'-methoxy-6',7'-dihydrospiro[piperidine-4,4'-thieno[3.2-c]pyran] (2a) was performed starting with 3-bromothiophene (3). After introduction of the acetaldehyde substructure (7), halogen metal exchange, addition of 1-benzylpiperidin-4-one, and cyclization led to the spirocyclic thienopyran 2a. The removal of the benzyl group afforded the secondary amine 2f, which was substituted with various residues. With respect to a, affinity the N-benzyl derivative 2a, the N-cyclohexylmethyl derivative 2d, and the N-p-fluorobenzyl derivative 2i represent the most potent compounds of this series binding with K-i values of 0.32, 0.29, and 0.62 nM, respectively. Electronic properties of the substituents have only little impact on sigma(1) affinity. The most potent sigma(1) ligands display high selectivity against sigma(2), 5-HT1A, 5-HT6, 5-HT7, alpha(1A), alpha(2), and NMDA receptors. The activity of 2a in the mouse capsaicin assay seems to indicate sigma(1) antagonistic activity.