3-methoxy-1-cyclohexyl-2-(ethylsulfanyl)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: 3-methoxy-1-cyclohexyl-2-(ethylsulfanyl)pyrrole
• 英文别名: 2-ethylthio-3-methoxy-N-cyclohexylpyrrole；1-cyclohexyl-2-ethylsulfanyl-3-methoxypyrrole
• 化学式: C₁₃H₂₁NOS
• 分子量: 239.382
• InChiKey: JDXXSBJGRNVABM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 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：

  环己基异硫氰酸脂 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 3-methoxy-1-cyclohexyl-2-(ethylsulfanyl)pyrrole
  参考文献：
  名称：

  Reaction of lithioalkoxyallenes with isothio-cyanates: Synthesis of pyrroles and 5,6-dihydropyridines

  摘要：

  DOI：

  10.1007/bf01165720

文献信息

• 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).
• Reaction of lithioalkoxyallenes with isothio-cyanates: Synthesis of pyrroles and 5,6-dihydropyridines
  作者：N. A. Nedolya、L. Brandsma、B. A. Trofimov

  DOI：10.1007/bf01165720

  日期：1996.7