2-pipecoline N-carbamate | 78999-63-0

• 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: 2-pipecoline N-carbamate
• 英文别名: α-methyl-piperidine；Methyl 2-methylpiperidine-1-carboxylate
• CAS: 78999-63-0
• 化学式: C₈H₁₅NO₂
• mdl: MFCD13179051
• 分子量: 157.213
• InChiKey: NDHBUUZJQUTHJU-UHFFFAOYSA-N

物化性质

• 沸点：
  92 °C(Press: 2 Torr)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-pipecoline N-carbamate 在 硝酸 、 三氟乙酸 作用下， 反应 3.0h， 以76%的产率得到4-(N-(methoxycarbonyl)formamido)pentanoic acid
  参考文献：
  名称：

  Oxidative C-C Bond Cleavage of N-Protected Cyclic Amines by HNO3-TFA System

  摘要：

  Oxidative C-C bond cleavage of N-protected cyclic amines was achieved by using 70% HNO3 in trifluoroacetic acid (TFA) to afford omega-amino acid derivatives in high yields. The C-C bond cleavage reaction smoothly proceeded under aerobic condition with a simple procedure. The use of 70% HNO3 as an oxidant source enabled to conduct the reaction at a higher substrate concentration than that of the previous condition using NaNO2 in TFA. In addition, some omega-amino acids were obtained with improved reaction efficiency under the present reaction conditions.

  DOI：

  10.3987/com-19-s(f)31
• 作为产物：
  描述：

  2-cyano-1-methoxycarbonylpiperidine 在 四乙基对甲苯磺酸铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-pipecoline N-carbamate
  参考文献：
  名称：

  有机化学139.腈的电还原脱氰及其在α-烷基胺合成中的应用

  摘要：

  当在含有Et 4 NOTs作为支持电解质的非质子传递溶剂（DMF或MeCN）中将Zn用作阴极材料时，腈的电还原得到相应的脱氰产物。通过使胺在α位氰化，然后将所得的α-氨基腈进行α-烷基化，然后进行电还原脱氰作用，可以有效地实现α-位胺的烷基化。

  DOI：

  10.1016/s0040-4020(01)80493-2

文献信息

• Direct electrochemical α-cyanation of N-protected cyclic amines
  作者：Samuel Shikuku Libendi、Yosuke Demizu、Osamu Onomura

  DOI：10.1039/b816598j

  日期：——

  α-Cyanation of N-protected cyclic amines was achieved using a direct electrochemical method. Unsubstituted N-protected cyclic amines were easily cyanated at the α-position using an undivided cell in high yields; moreover, α-cyanation of α′-substituted pyrrolidine and α′-,β′- or γ-substituted piperidines smoothly proceeded in high yield and with high to excellent diastereoselectivity. α-Substituted N-cyano-pyrrolidines and -piperidines were also cyanated at the more substituted position (the α-position) using a divided cell with high yield and high regioselectivity.

  通过直接电化学方法，实现了N-保护的环状胺的α-氰化。未取代的N-保护环状胺在无隔膜电池中易于在α位进行氰化，产率很高；此外，α'-取代的吡咯烷和α'、β'或γ-取代的哌啶也能顺利进行高产率的α-氰化，并具有高度至优异的非对映选择性。α-取代的N-氰基吡咯烷和哌啶在有隔膜电池中也能在更取代的位置（α位）进行氰化，产率高且具有高区域选择性。
• [EN] 2,5-DISUBSTITUTED PIPERIDINE OREXIN RECEPTOR ANTAGONISTS<br/>[FR] PIPÉRIDINES 2,5-DISUBSTITUÉES COMME ANTAGONISTES DU RÉCEPTEUR DE L'OREXINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2010048010A1

  公开（公告）日：2010-04-29

  The present invention is directed to 2,5-disubstituted piperidine amide compounds which are antagonists of orexin receptors, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which orexin receptors are involved.

  本发明涉及2,5-二取代哌啶酰胺化合物，这些化合物是促进睡眠的受体拮抗剂，可用于治疗或预防神经系统和精神疾病，以及涉及促进睡眠的疾病。该发明还涉及包含这些化合物的药物组合物，以及这些化合物和组合物在预防或治疗涉及促进睡眠的疾病中的用途。
• Synthesis of β-hydroxypiperidine alkaloids by anodic oxidation of carbamates and hydroboration
  作者：Mark Plehiers、Claude Hootelé

  DOI：10.1139/v96-273

  日期：1996.12.1

  (±)-pseudoconhydrine, (±)-N-methylpseudoconhydrine, (−)-5-hydroxysedamine, and (+)-sedacryptine were synthesized. Successive functionalization of the piperidine ring via anodic methoxylation allowed the regio- and stereoselective introduction of the substituents. The α and α′ substituents were introduced by application of the sequence elimination–nucleophilic addition from 2- or 2,5-substituted 6-methoxycarbamates

  合成了 β-羟基哌啶生物碱 (±)-pseudoconhydrine、(±)-N-methylpseudoconhydrine、(-)-5-hydroxysedamine 和 (+)-sedacryptine。通过阳极甲氧基化对哌啶环进行连续功能化，可以区域选择性和立体选择性地引入取代基。α 和 α' 取代基是通过应用 2- 或 2,5- 取代的 6-甲氧基氨基甲酸酯的序列消除 - 亲核加成引入的。硼氢化 - 烯氨基甲酸酯的氧化，通过从 α-甲氧基氨基甲酸酯中消除甲醇获得，允许引入 β-羟基官能团。关键词：生物碱，景天，N-acyliminium，烯氨基甲酸酯。
• A NEW SYNTHETIC METHOD OF 1-AZABICYCLO[4.<i>n</i>.0]SYSTEMS
  作者：Tatsuya Shono、Yoshihiro Matsumura、Kenji Tsubata、Kenji Inoue、Ryoichi Nishida

  DOI：10.1246/cl.1983.21

  日期：1983.1.5

  A new method for the synthesis of bicyclic pyridinium salts from alicyclic amines and reduction of the salts to 1-azabicyclo[4.n.0]systems has been exploited.

  已经开发了一种从脂环胺合成双环吡啶鎓盐并将盐还原为 1-氮杂双环 [4.n.0] 系统的新方法。
• Thienopyrrole compound and use thereof as HCV polymerase inhibitor
  申请人：Mizojiri Ryo

  公开号：US20060167246A1

  公开（公告）日：2006-07-27

  The present invention relates to a thienopyrrole compound represented by the following formula [I] wherein each symbol is as defined in the specification, or a pharmaceutically acceptable a salt thereof, and a hepatitis C virus (HCV) polymerase inhibitor and a therapeutic agent for hepatitis C containing this compound as an active ingredient. The compound of the present invention shows an anti-HCV activity based on the HCV polymerase inhibitory activity, and useful as an agent for the prophylaxis or treatment of hepatitis C.

  本发明涉及一种由下式[I]所表示的噻吡咯烷化合物，其中每个符号如规范中定义，或其药学上可接受的盐，以及一种丙型肝炎病毒（HCV）聚合酶抑制剂和含有该化合物作为活性成分的治疗剂。本发明的化合物基于HCV聚合酶抑制活性显示抗HCV活性，并且可用作丙型肝炎的预防或治疗剂。