(E)-2-methyl-1-(1-methylpiperidin-2-yl)pent-1-en-3-one | 639821-06-0

• 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: (E)-2-methyl-1-(1-methylpiperidin-2-yl)pent-1-en-3-one
• CAS: 639821-06-0
• 化学式: C₁₂H₂₁NO
• 分子量: 195.305
• InChiKey: GTWYJRCFEOWTHB-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (E)-2-methyl-1-(1-methylpiperidin-2-yl)pent-1-en-3-one 、 碘甲烷 以 甲醇 为溶剂， 反应 12.0h， 生成 1,1-Dimethyl-2-((E)-2-methyl-3-oxo-pent-1-enyl)-piperidinium; iodide
  参考文献：
  名称：

  Rigidified acetylcholine mimics: conformational requirements for binding to neuronal nicotinic receptors

  摘要：

  Rigidified derivatives have been designed and synthesized assuming the g + t conformer of acetylcholine (N-C-C-O = + 60degrees, C-C-O-C = 180degrees) as active conformation for binding to cytisine sensitive neuronal nicotinic receptors. The SAR of the compounds evaluated, along with those of more flexible analogues, support the g + t conformer hypothesis and highlight the stringent steric limitation of this nicotinic receptor sub-type. Compound 3e has low muM affinity for cytisine sensitive nicotinic receptor binding sites while being selective with regard to the a-bungarotoxin sensitive subclass. We also report few compounds with muM affinity for the a-bungarotoxin sensitive subclass. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00728-5
• 作为产物：
  描述：

  1-甲基-2-哌啶甲醇 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (E)-2-methyl-1-(1-methylpiperidin-2-yl)pent-1-en-3-one
  参考文献：
  名称：

  Rigidified acetylcholine mimics: conformational requirements for binding to neuronal nicotinic receptors

  摘要：

  Rigidified derivatives have been designed and synthesized assuming the g + t conformer of acetylcholine (N-C-C-O = + 60degrees, C-C-O-C = 180degrees) as active conformation for binding to cytisine sensitive neuronal nicotinic receptors. The SAR of the compounds evaluated, along with those of more flexible analogues, support the g + t conformer hypothesis and highlight the stringent steric limitation of this nicotinic receptor sub-type. Compound 3e has low muM affinity for cytisine sensitive nicotinic receptor binding sites while being selective with regard to the a-bungarotoxin sensitive subclass. We also report few compounds with muM affinity for the a-bungarotoxin sensitive subclass. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00728-5

文献信息

• Rigidified acetylcholine mimics: conformational requirements for binding to neuronal nicotinic receptors
  作者：Gérald Villeneuve、Danielle Cécyre、Hélène Lejeune、Marc Drouin、Ruoxi Lan、Rémi Quirion

  DOI：10.1016/s0960-894x(03)00728-5

  日期：2003.11

  Rigidified derivatives have been designed and synthesized assuming the g + t conformer of acetylcholine (N-C-C-O = + 60degrees, C-C-O-C = 180degrees) as active conformation for binding to cytisine sensitive neuronal nicotinic receptors. The SAR of the compounds evaluated, along with those of more flexible analogues, support the g + t conformer hypothesis and highlight the stringent steric limitation of this nicotinic receptor sub-type. Compound 3e has low muM affinity for cytisine sensitive nicotinic receptor binding sites while being selective with regard to the a-bungarotoxin sensitive subclass. We also report few compounds with muM affinity for the a-bungarotoxin sensitive subclass. (C) 2003 Elsevier Ltd. All rights reserved.