(2,2-Dimethoxy-ethyl)-((S)-1-methyl-heptyl)-amine | 155446-36-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,2-Dimethoxy-ethyl)-((S)-1-methyl-heptyl)-amine
• CAS: 155446-36-9
• 化学式: C₁₂H₂₇NO₂
• 分子量: 217.352
• InChiKey: DTHSTTKQNCZVEB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  15.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  30.49
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2,2-Dimethoxy-ethyl)-((S)-1-methyl-heptyl)-amine 在 盐酸 、 potassium thioacyanate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以84%的产率得到
  参考文献：
  名称：

  Chiral Azole Derivatives. 2. Synthesis of Enantiomerically Pure 1-Alkylimidazoles

  摘要：

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 7 (entries 1-7 in Table 1) under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 8, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 10 in good overall yield and high enantiomeric excess. In contrast, when applied to benzyl and benthydryl alcohols (entries 8-15), this sequence afforded the final compounds in good overall yield, but as racemic mixtures. The 1-(1-phenylalkyl)imidazole derivative (S)-(+)-24 was, however, prepared in enantiopure form starting from the corresponding (S)-(-)-alpha-methylbenzylamine (21) using the Marckwald procedure, which entailed the alkylation of 21 with bromoacetaldehyde dimethyl acetal, followed by the construction of the imidazole ring through reaction with potassium thiocyanate and final Ra-Ni desulfuration. Following the same procedure, (S)-(+)-10c was also synthesized, proving the stereochemical outcome of the Mitsunobu reaction.

  DOI：

  10.1021/jo00112a023
• 作为产物：
  描述：

  2-溴-1,1-二甲氧基乙烷 、 (S)-2-氨基辛烷 生成 (2,2-Dimethoxy-ethyl)-((S)-1-methyl-heptyl)-amine
  参考文献：
  名称：

  Stereospecific synthesis of 1-alkylimidazole derivatives via mitsunobu reactions

  摘要：

  4,5-Dicyanoimidazole has been reacted with racemic and enantiopure alcohols 1 under Mitsunobu conditions to give 1-alkyl-4,5-dicyanoimidazole derivatives 2, which in turn have been transformed by hydrolysis and decarboxylation into 1-alkylimidazoles 4 in good overall yield and high enantiomeric excess. The absolute stereochemistry of the compounds has been confirmed by synthesizing 4c through an independent route.

  DOI：

  10.1016/s0957-4166(00)86167-4