2-(allylsulfanyl)-1-isopropyl-3-methoxy-1H-pyrrole | 1369426-26-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(allylsulfanyl)-1-isopropyl-3-methoxy-1H-pyrrole
• 英文别名: 2-(Allylsulfanyl)-1-isopropyl-3-methoxypyrrole；3-methoxy-1-propan-2-yl-2-prop-2-enylsulfanylpyrrole
• CAS: 1369426-26-5
• 化学式: C₁₁H₁₇NOS
• 分子量: 211.328
• InChiKey: UUFPOGIKJMUKMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  以 四氢呋喃 、 正己烷 为溶剂， 生成 N-(1-(allylsulfanyl)-2-methoxy-(1-methylethylidene))buta-1,3-dien-1-amine 、 2-(allylsulfanyl)-1-isopropyl-3-methoxy-1H-pyrrole
  参考文献：
  名称：

  Reactions of 2-aza-1,3,5-trienes with superbases: competition between formation of thiazoles and azepines

  摘要：

  DOI：

  10.1007/s10593-012-0930-5

文献信息

• Further Developments in the Reaction of 2-Aza-1,3,5-trienes with Superbases: Competitive Formation of New 4,5-Dihydro-1,3-thiazoles, Dihydroazepines, and Azepines by Tandem Deprotonation–Cyclization
  作者：Nina Nedolya、Olga Tarasova、Alexander Albanov、Boris Trofimov

  DOI：10.1055/s-0034-1378805

  日期：——

  deprotonation of the methyl group or methylene fragment of the ketimine function of the same molecule, followed by [1,7]-electrocyclization, leads to seven-membered azaheterocycles, dihydroazepines and/or azepines. Allyl- and benzylsulfanyl-substituted 2-aza-1,3,5-trienes, which are readily available from alkoxyallenes, isothiocyanates, and allyl or benzyl bromide, are easily transformed into polyfunctionalized

  摘要 烯丙基-和苄基硫烷基取代的2-氮杂-1,3,5-三烯很容易转化为多官能化的4,5-二氢-1,3-噻唑（ 2-噻唑啉），方法是用超碱处理使活化的SCH 2基团去质子化，然后进行分子内[1,5]环闭合。同一分子的酮亚胺功能的甲基或亚甲基片段竞争性去质子化，然后进行[1,7]电环化，形成七元氮杂杂环，二氢氮杂和/或氮杂。 烯丙基-和苄基硫烷基取代的2-氮杂-1,3,5-三烯很容易转化为多官能化的4,5-二氢-1,3-噻唑（ 2-噻唑啉），方法是用超碱处理使活化的SCH 2基团去质子化，然后进行分子内[1,5]环闭合。同一分子的酮亚胺功能的甲基或亚甲基片段竞争性去质子化，然后进行[1,7]电环化，形成七元氮杂杂环，二氢氮杂和/或氮杂。
• Structural reorganization of (allyl-, benzyl-, and propargylsulfanyl)-substituted 2-aza-1,3,5-trienes in t-BuOK/THF/DMSO: access to rare functionalized 2-thiazolines
  作者：Nina A. Nedolya、Ol’ga A. Tarasova、Alexander I. Albanov、Boris A. Trofimov

  DOI：10.1016/j.tetlet.2014.03.015

  日期：2014.4

  Treatment of (allyl-, benzyl-, and propargylsulfanyl)-substituted 2-aza-1,3,5-trienes, which are readily accessible from lithiated methoxyallene, isopropyl isothiocyanate, and allyl, benzyl, or propargyl bromide, respectively, with t-BuOK in THF/DMSO resulted in the unexpected formation of 2-thiazoline derivatives along with seven-membered azaheterocycles [in the case of (allyl- and benzylsulfanyl)-substituted 2-aza-1,3,5-trienes]. An unprecedented structural reorganization of the azatrienes into 2-thiazolines presumably occurs via alpha-deprotonation of the substituents at the sulfur atom followed by intramolecular [1,5]-cyclization. Deprotonation of the ketimine fragment of the same molecule followed by [1,71-electrocyclization resulted in azepine ring formation. (C) 2014 Elsevier Ltd. All rights reserved.