N-Ethoxycarbonyl-1,2,3,4-tetrahydropyridine | 111054-54-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-Ethoxycarbonyl-1,2,3,4-tetrahydropyridine
• 英文别名: 1(2H)-Pyridinecarboxylic acid, 3,4-dihydro-, ethyl ester；ethyl 3,4-dihydro-2H-pyridine-1-carboxylate
• CAS: 111054-54-7
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: ATILYONFEASZNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  N-Ethoxycarbonyl-1,2,3,4-tetrahydropyridine 在 二甲基二环氧乙烷 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 ethyl (2R,3S)-3-hydroxy-2-[2-oxo-3-(4-oxoquinazolin-3-yl)propyl]piperidine-1-carboxylate
  参考文献：
  名称：

  α-取代的β-羟基哌啶和吡咯烷的制备：替非福定的全合成

  摘要：

  由环状烯氨基甲酸酯产生的环氧化物是有效的N-酰基亚胺鎓离子前体，并允许制备β-羟基，α-取代的哌啶和吡咯烷。还描述了外消旋的非布利福宁的总合成。

  DOI：

  10.1016/0040-4039(96)00527-8
• 作为产物：
  描述：

  哌啶酮 在 正丁基锂 、 magnesium sulfate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 N-Ethoxycarbonyl-1,2,3,4-tetrahydropyridine
  参考文献：
  名称：

  α-取代的β-羟基哌啶和吡咯烷的制备：替非福定的全合成

  摘要：

  由环状烯氨基甲酸酯产生的环氧化物是有效的N-酰基亚胺鎓离子前体，并允许制备β-羟基，α-取代的哌啶和吡咯烷。还描述了外消旋的非布利福宁的总合成。

  DOI：

  10.1016/0040-4039(96)00527-8

文献信息

• Sodium Borohydride-Nickel Chloride-Methanol Catalytic System for Regioselective Reduction of Electron-Rich Conjugated Dienes and Reductive Cleavage of Allyl Esters Involving π-Allylnickel Intermediates
  作者：Biao-Lin Yin、Cong-Bi Cai、Jin-Qiang Lai、Ze-Ren Zhang、Li Huang、Li-Wen Xu、Huan-Feng Jiang

  DOI：10.1002/adsc.201100612

  日期：2011.12

  The regioslective reduction of electron-rich dienes to monoolefins and the reductive cleavage of allyl esters were fulfilled by employing a sodium borohydride-nickel chloride-methanol catalytic system with exceedingly simple manipulations and high functional group tolerability. Both of the reductive reactions may involve π-allylnickel intermediates generated from fresh nickel boride.

  富电子二烯向单烯烃的区域反射还原和烯丙基酯的还原裂解是通过使用硼氢化钠-氯化镍-甲醇催化系统完成的，该系统操作极其简单，并且对官能团的耐受性极高。两种还原反应都可能涉及由新鲜的硼化镍产生的π-烯丙基镍中间体。
• Synthesis of new aza-bicyclic 2-isoxazolines by 1,3-dipolar cycloaddition of endocyclic enecarbamates and enamides with nitrile oxides
  作者：Valderes Moraes de Almeida、Rosiel José dos Santos、Alexandre José da Silva Góes、José Gildo de Lima、Carlos Roque Duarte Correia、Antônio Rodolfo de Faria

  DOI：10.1016/j.tetlet.2008.11.096

  日期：2009.2

  4-b]pyrrolidines, and 4,5-dihydroisoxazole[5,4-b]piperidines were synthesized in a highly regioselective manner through a 1,3-dipolar cycloaddition reaction of 5- and 6-membered endocyclic enecarbamates and enamides with several nitrile oxides in good to excellent yields. Hydrogenolysis of 5- and 6-membered Cbz-cycloadducts led to secondary amines, which presented distinctive stabilities. 2-Isoxazoline

  新型的氮杂双环2-异恶唑啉，4,5-二氢异恶唑[5,4- b ]吡咯烷和4,5-二氢异恶唑[5,4- b ]哌啶以高度区域选择性的方式通过1,3-偶极合成5元和6元环内氨基甲酸酯和酰胺与几种腈氧化物的环加成反应，收率良好或优异。5元和6元Cbz-环加合物的氢解反应生成仲胺，具有独特的稳定性。通过N-苯甲酰化，然后仲胺的氨解，或直接从环加合物的氨解，以高收率获得了2-异恶唑啉双酰胺。
• Facile Access to 6-Methoxy-1,2,3,6-tetrahydro- and 4-Hydroxy-1,2,3,4-tetrahydropyridines by Electrochemical Haloalkoxylation-Dehydrohalogenation Sequence as a Key Operation
  作者：Sigeru Torii、Tsutomu Inokuchi、Fumihiko Akahosi、Minoru Kubota

  DOI：10.1055/s-1987-27901

  日期：——

  A facile procedure for the synthesis of N-ethoxycarbonyl-6-methoxy-1,2,3,6-tetrahydropyridines 6 and N-ethoxycarbonyl-4-hydroxy-1,2,3,4-tetrahydropyridines 7 from piperidines 1 is described. The electrochemical halomethoxylation of N-ethoxycarbonyl-1,2,3,4-tetrahydropyridines 4 (easily accessible from 1 by ethoxycarbonylation followed by electrooxidative methoxylation and acid-catalyzed elimination of methanol) in a CH3OH-NR4X(X = Cl, Br, I)-(Pt)-(Pt) system provides N-ethoxycarbonyl-3-halo-2-methoxypiperidines 5 in 74-90 % yields. Dehydrohalogenation of iodides 5 (X = 1) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in toluene gave the desired olefin 6, which was isomerized in aqueous acetic acid to afford the alcohol 7 in 34-55% yields (from 5). The procedure is also applicable to the synthesis of seven membered derivatives 6f and 7f from 1f.

  描述了一种简便的合成方法，用于制备自哌啶1衍生的N-乙氧羰基-6-甲氧基-1,2,3,6-四氢吡啶6和N-乙氧羰基-4-羟基-1,2,3,4-四氢吡啶7。在CH3OH-NR4X（X=Cl，Br，I）-（Pt）-（Pt）体系中，通过N-乙氧羰基-1,2,3,4-四氢吡啶4（可通过乙氧羰基化、电氧化甲氧基化和酸催化甲醇消除从1便捷获得）的电化学卤甲氧基化反应，以74-90%的收率得到N-乙氧羰基-3-卤-2-甲氧基哌啶5。在甲苯中使用1,8-二氮杂二环[5.4.0]十一碳-7-烯（DBU）进行碘化物5的去卤化反应（X=I），得到所需烯烃6，该烯烃在乙酸水溶液中异构化，以34-55%的收率（从5计算）提供醇7。该方法同样适用于从1f合成七元环衍生物6f和7f。
• Aldol Reaction of Aromatic Acetals with Cyclic and Acyclic Alkyl Enol Ethers by Electrogenerated Acid (EG Acid) as a Catalyst
  作者：Tsutomu Inokuchi、Sadahito Takagishi、Keiji Ogawa、Yuji Kurokawa、Sigeru Torii

  DOI：10.1246/cl.1988.1347

  日期：1988.8.5

  Aldol reaction of aromatic acetals with alkyl enol ethers proceeds efficiently with electrogenerated acid (EG acid) independently prepared in an MeCN–NaClO4/Bu4NClO4–(Pt) system.

  芳香型缩醛与烷基烯醇醚的Aldol反应，在独立制备的乙腈-NaClO4/Bu4NClO4-(Pt)体系中电生酸（EG酸）的作用下高效进行。
• Differential oxidation of endocyclic enecarbamates. Synthesis of cyclic β-hydroxy-α-amino acids
  作者：Claudia H. Sugisaki、Patrick J. Carroll、Carlos Roque D. Correia

  DOI：10.1016/s0040-4039(98)00536-x

  日期：1998.5

  The differential oxidation of five and six-membered endocyclic enecarbamates was investigated employing m-CPBA, DMD, as well as enantioselective protocols such as the Kochi-Jacobsen-Katsuki's epoxidation and the Sharpless dihydroxylation. By this strategy the syntheses of beta-hydroxyprolines and beta-hydroxypipecolic acids were accomplished. X-Ray crystallographic analysis of the trans-beta-hydroxypipecolic acid was instrumental to solve structural assignment conflicts. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.