2-methoxy-N-cyclohexylidene-1-(ethyl-sulfanyl)buta-1,3-dien-1-amine | 184096-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methoxy-N-cyclohexylidene-1-(ethyl-sulfanyl)buta-1,3-dien-1-amine
• 英文别名: N-(1-ethylsulfanyl-2-methoxybuta-1,3-dienyl)cyclohexanimine
• CAS: 184096-63-7
• 化学式: C₁₃H₂₁NOS
• 分子量: 239.382
• InChiKey: LZZMUQYSXLXTJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  1-甲氧基-1,2-丙二烯 、 碘乙烷 、 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， 以11%的产率得到3-methoxy-1-cyclohexyl-2-(ethylsulfanyl)pyrrole
  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