6-甲基-3,4-二氢-1H-吡啶-2-酮 | 10333-14-9

• 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
• 中文名称: 6-甲基-3,4-二氢-1H-吡啶-2-酮
• 英文名称: 6-methyl-3,4-dihydro-1H-pyridin-2-one
• 英文别名: 6-methyl-1,2,3,4-tetrahydro-2-pyridone；6-methyl-3,4-dihydropyridin-2(1H)-one；3,4-dihydro-6-methylpyridin-2-one；6-Methyl-3,4-dihydro-1H-pyridin-2-on；3,4-dihydro-6-methyl-2-pyridone
• CAS: 10333-14-9
• 化学式: C₆H₉NO
• 分子量: 111.144
• InChiKey: AKOQCIDGAATASX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  6-甲基-3,4-二氢-1H-吡啶-2-酮 在 sodium tetrahydroborate 、 磺酰氯 、 高氯酸 、 2-硝基苯基丝氰酸酯 、 碘代三甲硅烷 、 三氟甲磺酸三甲基硅酯 、 双氧水 、 sodium carbonate 、 三乙胺 、 silver carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 反应 173.0h， 生成 (+/-)-huperazine B
  参考文献：
  名称：

  The First Total Synthesis of (±)-Huperzine B

  摘要：

  Huperzine B, a new Lycopodium alkaloid, exhibits a memory facilitating effect in mice and may be useful as an acetylcholinesterase inhibitor for the treatment of Alzheimer's disease. An efficient synthetic approach to huperzine B has been established successfully. The tetracyclic intermediate 10 is constructed by means of a tandem Michael addition and intramolecular Mannich cyclization using 8 and 9 as two components. Racemic huperzine B is obtained via a reaction sequence of 12 steps in 6.6% overall yield.

  DOI：

  10.1021/jo970248f
• 作为产物：
  描述：

  5-己烯酸 在 sodium azide 、 草酰氯 、 氨 、 碘 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 、 正戊烷 为溶剂， 反应 17.17h， 生成 6-甲基-3,4-二氢-1H-吡啶-2-酮
  参考文献：
  名称：

  Synthesis and reactions of iodo lactams

  摘要：

  DOI：

  10.1021/jo00252a024

文献信息

• Nitrogen Fixation: Synthesis of Heterocycles Using Molecular Nitrogen as a Nitrogen Source
  作者：Miwako Mori、Masaya Akashi、Masanori Hori、Katsutoshi Hori、Mayumi Nishida、Yoshihiro Sato

  DOI：10.1246/bcsj.77.1655

  日期：2004.9

  Nitrogen fixation using transition metals is a fascinating process. We have already reported on the incorporation of molecular nitrogen into organic compounds using a titanium–nitrogen complex reported by Yamamoto. We developed a novel titanium-catalyzed nitrogenation procedure using TiCl4 in the presence of an excess amount of Li and TMSCl. In this reaction, a 1 atm pressure of nitrogen gas can be used and the reaction proceeds at room temperature. The procedure is very simple. A THF solution of TiCl4 or Ti(OiPr)4 (1 equiv.), Li (10 equiv.), and TMSCl (10 equiv.) was stirred under an atmosphere of nitrogen at room temperature overnight to give titanium–nitrogen complexes. Although the structures of the titanium–nitrogen complexes have not yet been determined, they would consist of N(TMS)3, X2TiN(TMS)2, and XTi=NTMS. Using this procedure, various heterocycles, such as indole, quinoline, pyrrole, pyrrolizine, and indolizine derivatives, could be synthesized from molecular nitrogen in good-to-moderate yields as a stoichiometric reaction based on a titanium complex by a one-pot reaction. Furthermore, monomorine I and pumiliotoxin C were synthesized from molecular nitrogen as a nitrogen source. This procedure was further extended for the syntheses of heterocycles using a catalytic amount of titanium complex; also, indole and pyrrole derivatives were obtained in high yields.

  过渡金属固氮是一个迷人的过程。我们之前已经报道过使用Yamamoto报道的钛-氮配合物将分子氮引入有机化合物的方法。我们开发了一种新的钛催化氮化过程，使用TiCl4在过量Li和TMSCl的存在下进行。在这种反应中，可以使用1大气压的氮气，反应在室温下进行。这个过程非常简单。将TiCl4或Ti(OiPr)4（1 equiv.）、Li（10 equiv.）和TMSCl（10 equiv.）的THF溶液在氮气气氛下在室温下搅拌过夜，得到钛-氮配合物。尽管钛-氮配合物的结构尚未确定，但它们可能由N(TMS)3、X2TiN(TMS)2和XTi=NTMS组成。使用这种方法，可以通过钛配合物作为定量反应的单锅反应，以良好至中等的收率合成各种杂环化合物，如吲哚、喹啉、吡咯、吡咯啉和吲哚啉衍生物。此外，使用分子氮作为氮源合成了monomorine I和pumiliotoxin C。这种方法进一步扩展，用于使用催化量的钛配合物合成杂环化合物；此外，以高收率获得了吲哚和吡咯衍生物。
• Ruthenium-catalyzed hydration of nitriles and transformation of δ-ketonitriles to ene-lactams: total synthesis of (−)-pumiliotoxin C
  作者：Shun-Ichi Murahashi、Shigehiro Sasao、Eiichiro Saito、Takeshi Naota

  DOI：10.1016/s0040-4020(01)81902-5

  日期：1993.1

  1–2 equivalents of water can be performed efficiently by using RuH2(PPh3)4 catalyst to give the corresponding amides. Under the similar reaction conditions, δ-ketonitriles can be converted into the corresponding ene-lactams, which are versatile synthetic intermediates. The efficiency of the reaction is demonstrated by the short-step synthesis of (−)-pumiliotoxin C.

  通过使用RuH 2（PPh 3）4催化剂生成相应的酰胺，可以有效地用1-2当量的水进行腈水合。在相似的反应条件下，δ-乙腈可以转化为相应的烯-内酰胺，它们是通用的合成中间体。通过（-）-pumiliotoxin C的短步合成证明了反应的效率。
• Synthesis of Lactams via Copper-Catalyzed Intramolecular Vinylation of Amides
  作者：Tianshun Hu、Chaozhong Li

  DOI：10.1021/ol0505555

  日期：2005.5.1

  Copper-catalyzed intramolecular vinylation of iodoenamides were investigated for the first time. With CuI as the catalyst and N,N'-dimethylethylenediamine as the ligand, a number of iodoenamides underwent cyclization in dioxane leading to the formations of five- to seven-membered lactams in moderate to excellent yields.

  首次研究了铜催化的碘烯酰胺的分子内乙烯基化。以CuI为催化剂，以N，N'-二甲基乙二胺为配体，许多碘烯酰胺在二恶烷中环化，从而以中等至极好的收率形成了五元至七元内酰胺。
• Total Synthesis of (+)-Complanadine A Using an Iridium-Catalyzed Pyridine C−H Functionalization
  作者：Daniel F. Fischer、Richmond Sarpong

  DOI：10.1021/ja101893b

  日期：2010.5.5

  The total synthesis of the Lycopodium alkaloid complanadine A, which is an unsymmetrical dimer of lycodine, was achieved by exploiting a common tetracyclic precursor. Key to the success of the synthesis was the development of a late-stage site-selective C-H functionalization of a pyridine moiety to arrive at a key boronic ester intermediate.

  Lycopodium 生物碱 Complanadine A 的全合成是通过利用常见的四环前体实现的，它是 lycodine 的不对称二聚体。合成成功的关键是开发了吡啶部分的后期位点选择性 CH 官能化，以获得关键的硼酸酯中间体。
• Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids
  作者：Hannah M. S. Haley、Stefan E. Payer、Sven M. Papidocha、Simon Clemens、Jonathan Nyenhuis、Richmond Sarpong

  DOI：10.1021/jacs.1c00457

  日期：2021.3.31

  heterocycles through C–H functionalization and C–C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage

  氮杂环（氮杂环）是许多药物、农用化学品和天然产物中常见的结构基序。通过C-H官能化和C-C裂解方法选择性安装和修饰氮杂环的许多强大方法已经被开发出来并继续得到发展，揭示了包含这些结构实体的靶标合成的新策略。在这里，我们报告了石松碱型石松生物碱木麻黄碱 H、石松碱 B、石松碱 A 和石松碱 F 的首次全合成，以及通过易于获得的生物启发后期多样化来全合成 8,15-二氢石杉碱 A。常见前体， N-去甲基-β-暗色碱。合成中的关键步骤包括暗色中间体核心结构中哌啶环的氧化C-C键断裂以及吡啶核的位点选择性C-H硼基化以实现交叉偶联反应。