1,1'-dimethyl-2,3'-bipyrrolidinyl-2'-one | 6602-35-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1,1'-dimethyl-2,3'-bipyrrolidinyl-2'-one
• 英文别名: 2'-Oxo-1,1'-dimethyl-bipyrrolidinyl-(2,3')；2,3'-Dimethyl-2,3'-diaza-2'-oxo-bi-cyclopentyl-(1,1')；1,1'-dimethyl-octahydro-[2,3']bipyrrolyl-2'-one；1-Methyl-3-(1-methylpyrrolidin-2-yl)pyrrolidin-2-one；1-methyl-3-(1-methylpyrrolidin-2-yl)pyrrolidin-2-one
• CAS: 6602-35-3
• 化学式: C₁₀H₁₈N₂O
• 分子量: 182.266
• InChiKey: ALCPDGSSDUDYHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1'-dimethyl-2,3'-bipyrrolidinyl-2'-one 在 lithium aluminium tetrahydride 作用下， 生成 1,1'-dimethyl-2,3'-bipyrrolidinyl
  参考文献：
  名称：

  Identification and synthesis of novel alkaloids from the root system of Nicotiana tabacum: Affinity for neuronal nicotinic acetylcholine receptors

  摘要：

  A novel pyridine derivative, 3,5-bis-(1-methyl-pyrrolidin-2-yl)-pyridine, and a pair of diastereomers of 1,1'-dimethyl-[2,3]bipyrrolidinyl were isolated from the root of Nicotiana tabacum plants and identified as novel alkaloids by GC-MS analysis. The structures of these new alkaloids were confirmed by total synthesis. The affinities of these novel alkaloids, and other structurally related compounds for alpha L beta 2*, alpha 7* neuronal nicotinic acetylcholine receptors (nAChRs), and for nAChRs mediating nicotine-evoked dopamine release from rat striatum were also assessed. The results indicate that these compounds do not interact with alpha 7* nAChRs, but inhibit [H-3]nicotine binding to the alpha 4 beta 2* nAChR subtype. The results also demonstrate that these compounds act as antagonists at nAChRs mediating nicotine-evoked dopamine release from rat striatum. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2005.09.009
• 作为产物：
  描述：

  N-甲基吡咯烷酮 在 钯 氢气 、 三氯氧磷 作用下， 生成 1,1'-dimethyl-2,3'-bipyrrolidinyl-2'-one
  参考文献：
  名称：

  Identification and synthesis of novel alkaloids from the root system of Nicotiana tabacum: Affinity for neuronal nicotinic acetylcholine receptors

  摘要：

  A novel pyridine derivative, 3,5-bis-(1-methyl-pyrrolidin-2-yl)-pyridine, and a pair of diastereomers of 1,1'-dimethyl-[2,3]bipyrrolidinyl were isolated from the root of Nicotiana tabacum plants and identified as novel alkaloids by GC-MS analysis. The structures of these new alkaloids were confirmed by total synthesis. The affinities of these novel alkaloids, and other structurally related compounds for alpha L beta 2*, alpha 7* neuronal nicotinic acetylcholine receptors (nAChRs), and for nAChRs mediating nicotine-evoked dopamine release from rat striatum were also assessed. The results indicate that these compounds do not interact with alpha 7* nAChRs, but inhibit [H-3]nicotine binding to the alpha 4 beta 2* nAChR subtype. The results also demonstrate that these compounds act as antagonists at nAChRs mediating nicotine-evoked dopamine release from rat striatum. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.lfs.2005.09.009

文献信息

• Identification and synthesis of novel alkaloids from the root system of Nicotiana tabacum: Affinity for neuronal nicotinic acetylcholine receptors
  作者：Xiaochen Wei、Sangeetha P. Sumithran、A. Gabriela Deaciuc、Harold R. Burton、Lowell P. Bush、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1016/j.lfs.2005.09.009

  日期：2005.12

  A novel pyridine derivative, 3,5-bis-(1-methyl-pyrrolidin-2-yl)-pyridine, and a pair of diastereomers of 1,1'-dimethyl-[2,3]bipyrrolidinyl were isolated from the root of Nicotiana tabacum plants and identified as novel alkaloids by GC-MS analysis. The structures of these new alkaloids were confirmed by total synthesis. The affinities of these novel alkaloids, and other structurally related compounds for alpha L beta 2*, alpha 7* neuronal nicotinic acetylcholine receptors (nAChRs), and for nAChRs mediating nicotine-evoked dopamine release from rat striatum were also assessed. The results indicate that these compounds do not interact with alpha 7* nAChRs, but inhibit [H-3]nicotine binding to the alpha 4 beta 2* nAChR subtype. The results also demonstrate that these compounds act as antagonists at nAChRs mediating nicotine-evoked dopamine release from rat striatum. (c) 2005 Elsevier Inc. All rights reserved.