2,5-dimethoxy-6-(methylsulfanyl)-2,3-dihydropyridine | 494747-08-9

• 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
• 英文名称: 2,5-dimethoxy-6-(methylsulfanyl)-2,3-dihydropyridine
• 英文别名: Pyridine, 2,3-dihydro-2,5-dimethoxy-6-(methylthio)-(9CI)；2,5-dimethoxy-6-methylsulfanyl-2,3-dihydropyridine
• CAS: 494747-08-9
• 化学式: C₈H₁₃NO₂S
• 分子量: 187.263
• InChiKey: NFDZJJUSZZVHDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  56.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-dimethoxy-6-(methylsulfanyl)-2,3-dihydropyridine 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以72%的产率得到3-methoxy,2-methylthiopyridine
  参考文献：
  名称：

  Synthesis and easy aromatisation of 5-substituted 6-(alkylthio)-2-methoxy-2,3-dihydropyridines. A new approach to the pyridine ring

  摘要：

  Reaction of lithiated methoxyallene, 1-ethoxyethoxyallene, 1-(methylthio)propyne and 2-butyne with methoxymethyl isothiocyanate, MeOCH2N=C=S followed by methylation affords the imidothioates H2C=C=C(R)C(SMe)=NCH2OMe [R=Me, OMe, OCH(Me)OEt, SMe]. Rearrangement to the fully conjugated Systems H2C=CH-C(R)=C(SMe)-N=CHOMe and subsequent electrocyclisation of these compounds leads to the 5-substituted 6-(methylthio)-2-methoxy-2,3-dihydropyridines with good to excellent yields. In the presence of acidic catalysts or by heating at elevated temperatures these dihydropyridines eliminate methanol to afford 3-substituted 2-(methylthio)pyridines. The aroma compound 2-(methylthio)-3-pyridinol was obtained by acid-catalysed treatment of 3-(1-ethoxyethoxy)-2-(methylthio)pyridine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02423-1
• 作为产物：
  描述：

  methyl-N-[1-(methylsulfanyl)-2-methoxy-1,3-butadienyl]iminoformate 以73%的产率得到2,5-dimethoxy-6-(methylsulfanyl)-2,3-dihydropyridine
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1020332313966

文献信息

• Allenic Compounds and Isothiocyanates as Key Building Units in the Synthesis of Heterocycles
  作者：Lambert Brandsma、Nina A. Nedolya

  DOI：10.1055/s-2004-816005

  日期：——

  attack of the thiolate moiety on the allenic system and subsequent addition of methyl iodide or protonation. 1 Introduction 2 Generation of Allenic Lithium Compounds 3 Formation of 2,3-Dihydropyridines or Mixtures of 2,3-Dihydropyridines and Pyrroles 4 Directed Synthesis of Pyrroles 5 Synthesis of Quinolines 6 Synthesis of Cyclobutanopyrrolines 7 Synthesis of Thiophene and Dihydrothiophene Derivatives

  锂化的丙二烯化合物和异硫氰酸酯之间的反应，R'N=C=S，在大多数情况下只产生具有丙二烯结构的硫代亚胺酸盐，C=C=CC(SLi)=NR 1 。这些中间体已用于制备 2,3-二氢吡啶、吡咯、喹啉、环丁吡咯啉和噻吩或二氢噻吩衍生物的新方法。产生环中具有氮原子的杂环的过程包括 5-烷基化，然后简单加热或用卤化铜 (I) 处理。2-氨基噻吩和 2-亚氨基-2,5-二氢噻吩是通过硫醇部分对丙二烯体系的分子内亲核攻击和随后添加甲基碘或质子化形成的。1 引言 2 艾伦锂化合物的生成 3 2,3-二氢吡啶或 2 的混合物的形成，
• Reactions of heterocumulenes with organometallic reagents: XVII. One-pot synthesis of alkoxy and (alkylsulfanyl)-substituted pyrroles and 2,3-dihydropyridines from aliphatic isothiocyanates and lithiated alkoxyallenes
  作者：N. A. Nedolya、L. Brandsma、O. A. Tarasova、A. I. Albanov、B. A. Trofimov

  DOI：10.1134/s1070428011050034

  日期：2011.5

  A fundamentally new approach was developed to designing pyrrole and dihydropyridine rings from available allenes and isothiocyanates involving a single preparative stage. Applying the reaction of lithiated alkoxyallenes with aliphatic isothiocyanates we have synthesized previously unknown 1-alkyl(cycloalkyl) pyrroles and 2,3-dihydropyridines with rare alkoxy- and alkylsulfanyl substituents. It was proved that the five- and six-membered azaheterocycles formed as a result of competing reactions of direct intramolecular cyclization of S-alkylated adducts of lithiated alkoxyallenes with isothiocyanates (1-aza-1,3,4-trienes) into pyrroles and of [1,5]-sigmatropic rearrangement into conjugated 2-aza-1,3,5-trienes with subsequent closure into dihydropyridine ring (through 6 pi-electrocyclization).
• Synthesis and easy aromatisation of 5-substituted 6-(alkylthio)-2-methoxy-2,3-dihydropyridines. A new approach to the pyridine ring
  作者：Nina A. Nedolya、Nataly I. Schlyakhtina、Lyudmila V. Klyba、Igor A. Ushakov、Sergei V. Fedorov、Lambert Brandsma

  DOI：10.1016/s0040-4039(02)02423-1

  日期：2002.12

  Reaction of lithiated methoxyallene, 1-ethoxyethoxyallene, 1-(methylthio)propyne and 2-butyne with methoxymethyl isothiocyanate, MeOCH2N=C=S followed by methylation affords the imidothioates H2C=C=C(R)C(SMe)=NCH2OMe [R=Me, OMe, OCH(Me)OEt, SMe]. Rearrangement to the fully conjugated Systems H2C=CH-C(R)=C(SMe)-N=CHOMe and subsequent electrocyclisation of these compounds leads to the 5-substituted 6-(methylthio)-2-methoxy-2,3-dihydropyridines with good to excellent yields. In the presence of acidic catalysts or by heating at elevated temperatures these dihydropyridines eliminate methanol to afford 3-substituted 2-(methylthio)pyridines. The aroma compound 2-(methylthio)-3-pyridinol was obtained by acid-catalysed treatment of 3-(1-ethoxyethoxy)-2-(methylthio)pyridine. (C) 2002 Elsevier Science Ltd. All rights reserved.
• ——
  作者：N. A. Nedolya、L. Brandsma、N. I. Shlyakhtina

  DOI：10.1023/a:1020332313966

  日期：——
• Aromatization of 2,3-dihydropyridines controlled with substituents
  作者：N. A. Nedolya、O. A. Tarasova、A. I. Albanov、B. A. Trofimov

  DOI：10.1134/s1070428015020268

  日期：2015.2

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