(R)-(-)-2-(N,N-dipropylaminomethyl)piperidine | 267220-52-0

• 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: (R)-(-)-2-(N,N-dipropylaminomethyl)piperidine
• 英文别名: N-[[(2R)-piperidin-2-yl]methyl]-N-propylpropan-1-amine
• CAS: 267220-52-0
• 化学式: C₁₂H₂₆N₂
• 分子量: 198.352
• InChiKey: JECMDTMOQOVPIU-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-2-(N,N-dipropylaminomethyl)piperidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 N-(2-[(2R)-2-[(dipropylamino)methyl]piperidin-1-yl]ethyl)-6-oxo-5H-pyrido[2,3-b][1,4]benzodiazepine-11-carboxamide
  参考文献：
  名称：

  Syntheses of R and S isomers of AF-DX 384, a selective antagonist of muscarinic M 2 receptors

  摘要：

  Enantiomers of 5,11-dihydro-11-[2-[2-[(N,N-dipropylaminomethyl)piperidin-1-yl]ethylamino]-carabonyl]-6H-pyrido[2,3- b][1,4]benzodiazepin-6-one (AF-DX 384) 1, have been synthesized from (S)-(+) and (R)-(-)-2-[N,N-dipropylaminomethyl]piperidine 4. The enantiomeric excess of 1 has been determined by capillary electrophoresis by using the alpha-highly sulphated cyclodextrin (alpha-HSCD) as chiral selector within the running electrolyte. (S)-(+)-(4) was prepared from (S)-(-)-pipecolic acid in a 4-step procedure (overall yield: 30%, ee: 99%) and (R)-(-)-AF-DX 384 from (R)-(+)-pipecolic acid. The (R)-(-) isomer exhibited in vitro a 23-fold higher affinity than its enantiomer (S)-(+) towards muscarinic receptors of subtype 2. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00307-7
• 作为产物：
  描述：

  (R)-[(N-methoxycarbonyl)piperidine]-2-dicyclohexylammonium carboxylate 在 吡啶 、 lithium aluminium tetrahydride 、 氯化亚砜 、 碘代三甲硅烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 生成 (R)-(-)-2-(N,N-dipropylaminomethyl)piperidine
  参考文献：
  名称：

  Syntheses of R and S isomers of AF-DX 384, a selective antagonist of muscarinic M 2 receptors

  摘要：

  Enantiomers of 5,11-dihydro-11-[2-[2-[(N,N-dipropylaminomethyl)piperidin-1-yl]ethylamino]-carabonyl]-6H-pyrido[2,3- b][1,4]benzodiazepin-6-one (AF-DX 384) 1, have been synthesized from (S)-(+) and (R)-(-)-2-[N,N-dipropylaminomethyl]piperidine 4. The enantiomeric excess of 1 has been determined by capillary electrophoresis by using the alpha-highly sulphated cyclodextrin (alpha-HSCD) as chiral selector within the running electrolyte. (S)-(+)-(4) was prepared from (S)-(-)-pipecolic acid in a 4-step procedure (overall yield: 30%, ee: 99%) and (R)-(-)-AF-DX 384 from (R)-(+)-pipecolic acid. The (R)-(-) isomer exhibited in vitro a 23-fold higher affinity than its enantiomer (S)-(+) towards muscarinic receptors of subtype 2. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00307-7

文献信息

• Syntheses of R and S isomers of AF-DX 384, a selective antagonist of muscarinic M 2 receptors
  作者：Juliette Martin、Annamaria Deagostino、Cécile Perrio、François Dauphin、Christophe Ducandas、Christophe Morin、Paul-Louis Desbène、Marie Claire Lasne

  DOI：10.1016/s0968-0896(99)00307-7

  日期：2000.3

  Enantiomers of 5,11-dihydro-11-[2-[2-[(N,N-dipropylaminomethyl)piperidin-1-yl]ethylamino]-carabonyl]-6H-pyrido[2,3- b][1,4]benzodiazepin-6-one (AF-DX 384) 1, have been synthesized from (S)-(+) and (R)-(-)-2-[N,N-dipropylaminomethyl]piperidine 4. The enantiomeric excess of 1 has been determined by capillary electrophoresis by using the alpha-highly sulphated cyclodextrin (alpha-HSCD) as chiral selector within the running electrolyte. (S)-(+)-(4) was prepared from (S)-(-)-pipecolic acid in a 4-step procedure (overall yield: 30%, ee: 99%) and (R)-(-)-AF-DX 384 from (R)-(+)-pipecolic acid. The (R)-(-) isomer exhibited in vitro a 23-fold higher affinity than its enantiomer (S)-(+) towards muscarinic receptors of subtype 2. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.