ethyl-2-tert-butoxy-N-methylbuta-2,3-dienimidothioate | 1315270-21-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫基化合物
• 英文名称: ethyl-2-tert-butoxy-N-methylbuta-2,3-dienimidothioate
• 英文别名: ethyl N-methyl-2-[(2-methylpropan-2-yl)oxy]buta-2,3-dienimidothioate
• CAS: 1315270-21-3
• 化学式: C₁₁H₁₉NOS
• 分子量: 213.344
• InChiKey: BAXSTKXSCSZORP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  tert-butoxyallene 、 碘乙烷 、 异硫氰酸甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 ethyl-2-tert-butoxy-N-methylbuta-2,3-dienimidothioate
  参考文献：
  名称：

  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

  摘要：

  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).

  DOI：

  10.1134/s1070428011050034