(+/-)-(1-methyl-[2]piperidyl)-acetone; hydrochloride | 34893-55-5

• 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-methyl-[2]piperidyl)-acetone; hydrochloride
• 英文别名: (+/-)-(1-Methyl-[2]piperidyl)-aceton; Hydrochlorid；1-(1-methylpiperidin-2-yl)propan-2-one;hydrochloride
• CAS: 34893-55-5
• 化学式: C₉H₁₇NO*ClH
• 分子量: 191.701
• InChiKey: MLQCDBFOFADVPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(1-methyl-[2]piperidyl)-acetone; hydrochloride 、 碘甲烷 以 甲醇 为溶剂， 反应 12.0h， 生成 2-acetonyl-1,1-dimethyl-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：

  2-(2-chloroethyl)-1-methylpiperidine 在 盐酸 、 正丁基锂 、 四甲基乙二胺 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 甲醇 为溶剂， 反应 7.5h， 生成 (+/-)-(1-methyl-[2]piperidyl)-acetone; hydrochloride
  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

• TAKAHATA, HIROKI;TAKAHASHI, KOICHI;WANG, ENG-CHI;YAMAZAKI, TAKAO, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 1211-1214
  作者：TAKAHATA, HIROKI、TAKAHASHI, KOICHI、WANG, ENG-CHI、YAMAZAKI, TAKAO

  DOI：——

  日期：——
• 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.