1-ethyl-3-methoxy-2-methylsulfanyl-1H-pyrrole

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-ethyl-3-methoxy-2-methylsulfanyl-1H-pyrrole
• 英文别名: 2-(methylsulfanyl)-3-methoxy-1-ethylpyrrole；1-ethyl-3-methoxy-2-methylsulfanylpyrrole
• 化学式: C₈H₁₃NOS
• 分子量: 171.263
• InChiKey: MEUYETDKGMTXBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  39.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl N-ethyl-2-methoxybuta-2,3-dienimidothioate 在 copper(I) bromide 作用下， 生成 1-ethyl-3-methoxy-2-methylsulfanyl-1H-pyrrole
  参考文献：
  名称：

  新杂环的质谱：X. 1-烷基（环烷基，芳基）-3-烷氧基（芳基）-2-甲基硫烷基-1 H-吡咯的分子离子的断裂

  摘要：

  研究了以前未知的1-烷基（环烷基，芳基）-3-烷氧基（芳基）-2-甲基硫基-1 H-吡咯的质谱。所有3-烷氧基取代的吡咯在电子轰击（70 eV）下的裂解均遵循醚和硫化物的分解路径。特别是1-R-取代的3-甲氧基-2-甲基硫烷基-1 H-吡咯（R ＝ Me，Et，i- Pr，s- Bu，环-C 5 H 9，环-C 6 H 11，Ph ）从甲氧基和甲基硫烷基基团失去甲基基团。1秒的质谱丁基和1环烷基吡咯也有一个强峰（10-49％），该峰来自通过同步氢转移裂解NR键形成的奇电子[ M C n H 2 n ] +·离子。3-烷氧基-1-异丙基-2-甲基硫烷基-1 H-吡咯（Alk = Et，i -Pr，t -Bu）断裂中的O-Alk键断裂伴随重排过程，导致相应的烯烃和1-电子的1-异丙基-2-甲基硫烷基-1 H-吡咯-3-醇离子。1-烷基-2-甲基硫烷基-3-苯基-1 H-吡咯的主要裂解途径（Alk

  DOI：

  10.1134/s1070428010070134

文献信息

• Application of copper catalysis in a one-pot procedure for 1-alkyl-3-methoxy-2-methylthiopyrroles starting from methoxyallene and alkyl isothiocyanates
  作者：Nina A. Nedolya、Lambert Brandsma、Olga A. Tarasova、Hermann D. Verkruijsse、Boris A. Trofimov

  DOI：10.1016/s0040-4039(98)00211-1

  日期：1998.4

  1-Alkyl-3-methoxy-2-methylthiopyrroles are obtained with high purities and in high yields by Cu(I)halide-catalyzed cyclization of the products from addition of 1-lithiomethoxyallene to alkyl isothiocyanates and subsequent methylation. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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).
• Unexpected transformations of 1-aza-1,3,4-trienes in alcoholic potassium hydroxide. New classes of aza dienes
  作者：N. A. Nedolya、O. A. Tarasova、O. G. Volostnykh、A. I. Albanov、B. A. Trofimov

  DOI：10.1134/s1070428011010209

  日期：2011.1
• Unexpected elimination of methanol from 6-(alkylsulfanyl)-5-methoxy-2,3-dihydropyridines using t-BuOK-DMSO: an access to 2-alkyl-6-(alkyl-sulfanyl)pyridines
  作者：N. A. Nedolya、O. A. Tarasova、A. I. Albanov、B. A. Trofimov

  DOI：10.1007/s10593-011-0706-3

  日期：2011.3