(S)-(-)-(N,N-dipropyl)piperidine-2-carboxamide | 267220-63-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-(-)-(N,N-dipropyl)piperidine-2-carboxamide
• 英文别名: (2S)-N,N-dipropylpiperidine-2-carboxamide
• CAS: 267220-63-3
• 化学式: C₁₂H₂₄N₂O
• 分子量: 212.335
• InChiKey: KXNMHTGCARMCPJ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)-(N,N-dipropyl)piperidine-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (S)-(-)-[2-(N',N'-dipropylaminomethyl)piperidin-1-yl]-acetonitrile
  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：

  (S)-(-)-N,N-dipropyl [(N'-methoxycarbonyl)piperidine]-2-carboxamide 在 碘代三甲硅烷 、 甲醇 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以88%的产率得到(S)-(-)-(N,N-dipropyl)piperidine-2-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

文献信息

• Efficient Deracemization of Pipecolic Acid Amides through Enantioselective Protonation of Their Lithium Enolates: Insights into the Origin of the Transferred Proton
  作者：Juliette Martin、Jean-Christophe Plaquevent、Jacques Maddaluno、Jacques Rouden、Marie-Claire Lasne

  DOI：10.1002/ejoc.200900726

  日期：2009.11

  alkoxide/nBuLi” were the only bases to allow complete formation of the enolate in conjunction with high stereocontrol of the protonation. Experiments with (+)- or(–)-ephedrine derivatives as chiral sources and deuteriated reagents gave evidence that both the OH and NH protons of ephedrine were involved in the stereoinduction. External delivery of the proton was mainly operative with the aniline derivative (+)-5,

  报道了哌可酸酰胺去外消旋的详细研究。使用市售麻黄碱对这些酰胺的烯醇锂进行对映选择性质子化导致对映体过量（ee 值）高于 99%。反应的成功很大程度上取决于以下参数：碱、反应温度、手性源的结构和非手性猝灭剂。sBuLi 和双金属碱“钾醇盐/nBuLi”是唯一允许完全形成烯醇化物并结合质子化的高立体控制的碱。用 (+)- 或 (-)- 麻黄碱衍生物作为手性来源和氘化试剂的实验证明麻黄碱的 OH 和 NH 质子都参与了立体诱导。如氘标记实验所示，质子的外部传递主要通过苯胺衍生物 (+)-5 起作用，而内部淬灭是使用麻黄碱观察到的主要途径 (6)。最后，脱消旋过程成功地用于从外消旋哌可酸制备 N-保护的哌可酸的两种对映异构体（总产率为 51%，ee 为 99%）。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国， 2009)
• 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.