3,4-dihydro-1(2H)-pyridinecarboxaldehyde | 61157-70-8

• 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: 3,4-dihydro-1(2H)-pyridinecarboxaldehyde
• 英文别名: 3,4-dihydro-2H-pyridine-1-carboxaldehyde；1-formyl-1,2,3,4-tetrahydro-pyridine；1-formyl-1,2,3,4-tetrahydropyridine；N-formylpiperidene；1-Formyl-Δ²-piperidein；1-Formyl-1,2,3,4-tetrahydropyridin；3,4-dihydro-2H-pyridine-1-carbaldehyde
• CAS: 61157-70-8
• 化学式: C₆H₉NO
• 分子量: 111.144
• InChiKey: IMUULUQUUGIQCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-1(2H)-pyridinecarboxaldehyde 在 palladium on activated charcoal silver orthophosphate 、 Pd⁽⁰⁾-(R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl 、 氢气 、 四氯化钛 、 L-Selectride 、 苯基溴化镁 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 生成 (5SR,8aRS)-5-propylhexahydroindolizin-3(2H)-one
  参考文献：
  名称：

  Asymmetric Heck cyclization route to indolizidine and azaazulene alkaloids: synthesis of (+)-5-epiindolizidine 167B and indolizidine 223AB

  摘要：

  Asymmetric intramolecular Heck cyclization of endocyclic enamides occurs at room temperature to give indoloizidine and azaazulene ring systems in up to 86% enantiomeric excess. A synthesis of (+)-epiindolizidine 167B and formal synthesis of 5E,9Z-indolizidine 223AB is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01361-2
• 作为产物：
  描述：

  哌啶-1-甲醛 在 四乙基对甲苯磺酸铵 、 氯化铵 作用下， 生成 3,4-dihydro-1(2H)-pyridinecarboxaldehyde
  参考文献：
  名称：

  Stereoselective synthesis of azasugars by electrochemical oxidation

  摘要：

  A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was Successively used for the conversion of N-protected piperidines to N-protected 1-methoxypiperidines and for the conversion of 1-methoxy-2,3-didehydropiperidine derivatives to 1,2,3-triacetoxypiperidine derivatives. The method provided a new synthetic route to 2S,3S,6-triacetoxy-5S-methylpiperidine and 2R,3R,6-triacetoxy-5S-methylpiperidine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.036

文献信息

• Substitution reactions of 2-phenylsulphonyl-piperidines and -pyrrolidines with carbon nucleophiles: Synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone
  作者：Dearg S. Brown、Philippe Charreau、Thomas Hansson、Steven V. Ley

  DOI：10.1016/s0040-4020(01)86388-2

  日期：1991.1

  treatment with benzenesulphinic acid. On reaction with various carbon nucleophiles these sulphones gave good yields of substitution products. Typical nucleophiles used in these studies were organometallic reagents derived from Grignard reagents and zinc halide together with silyl enol ethers, silyl ketene acetals, allylsilanes and trimethylsilyl cyanide in the presence of a Lewis acid. These methods

  通过用苯磺酸进行处理，由相应的N-酰基氨基缩醛制备几种2-苯基磺酰基-哌啶和-吡咯烷。在与各种碳亲核试剂反应时，这些砜产生了良好的取代产物收率。这些研究中使用的典型亲核试剂是衍生自Grignard试剂的有机金属试剂和卤化锌，以及在路易斯酸存在下的甲硅烷基烯醇醚，甲硅烷基烯酮缩醛，烯丙基硅烷和三甲基甲硅烷基氰化物。这些方法被用于合成两种天然产物生物碱。去甲去氧肾上腺素（38）和Ruspolinone（40）。
• Regiocontrolled synthesis of (hetero)aryl and alkenyl dehydropyrrolidines, dehydropiperidines and azepenes by Ru-catalyzed, heteroatom-directed α-C–H activation/cross-coupling of cyclic enamides with boronic acids
  作者：Timothy K. Beng、Spencer Langevin、Hannah Braunstein、Monique Khim

  DOI：10.1039/c5ob02263k

  日期：——

  The synthesis of α-aryl and alkenyl pyrrolidine-, piperidine-, and azepane derivatives, through the intermediacy of cyclic enamides is described. The desired outcome is achieved through ruthenium-catalyzed, site-selective sp2 C–H activation/cross-coupling with aryl and alkenyl boronic acids. The regioselectivity (α-sp2vs. α-sp3vs. β-sp2 C–H functionalization) is governed by the rate differences between

  描述了通过环酰胺的中间体合成α-芳基和烯基吡咯烷-，哌啶-和氮杂环庚烷衍生物。理想的结果是通过钌催化的，位点选择性的sp 2 C H活化/与芳基和烯基硼酸交叉偶联而实现的。区域选择性（α-SP 2 VS。α-SP 3 VS。β-SP 2 C-H官能化）是通过SP之间的速率差支配2和SP 3的钌金属和之间C-H活化和必要性螯合羰基导向基团。
• Iridium-catalyzed α-alkynylation of cyclic nonaromatic eneformamides: application to the synthesis of azapolycyclic architectures
  作者：Timothy K. Beng、Francine Wanjiku

  DOI：10.1039/c9nj00003h

  日期：——

  A regioselective and chelation-assisted dehydrogenative alkynylation of cyclic nonaromatic eneformamides with terminal alkynes, under iridium catalysis, is described.

  一种在铱催化下进行的具有区域选择性和螯合辅助的环状非芳香烯酰胺与末端炔烃的脱氢烯基化反应被描述。
• Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine
  作者：Noriaki Moriyama、Yoshihiro Matsumura、Masami Kuriyama、Osamu Onomura

  DOI：10.1016/j.tetasy.2009.11.028

  日期：2009.12

  A new method using electrochemical oxidation and/or OsO4 oxidation has been used for the stereoselective synthesis of 2,3,6-trihydroxylated (5S)-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-protected 1-methoxpiperidines and for the conversion of 2,3-didehydro-1-methoxypiperidine derivatives to 2,3-trans-1,2,3-triacetoxypiperidine derivatives. These triacetates were easily transformed into (2S,3S)-6-triacetoxy-(5S)-methylpiperidine and (2R,3R)-6-triacetoxy-(5S)-methylpiperidine. In addition, the 2,3-cis-dihydroxylation of 2,3-didehydro-1-methoxypiperidine derivatives with OsO4 afforded (2R,3S)-6-triacetoxy-(5S)-methylpiperidine and (2S,3R)-(3-triacetoxy-(5S)-methylpiperidine. (C) 2009 Elsevier Ltd. All rights reserved.
• Regioselective palladium-catalyzed tandem .alpha.-arylation/isomerization of cyclic enamides
  作者：Kristina Nilsson、Anders Hallberg

  DOI：10.1021/jo00295a041

  日期：1990.4