N-(R)-(3,7-Dimethyl-6-octenylidene)-o-toluidine

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-(R)-(3,7-Dimethyl-6-octenylidene)-o-toluidine
• 英文别名: (3R)-3,7-dimethyl-N-(2-methylphenyl)oct-6-en-1-imine
• 化学式: C₁₇H₂₅N
• 分子量: 243.392
• InChiKey: AYXNTCWHAZULHR-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (+)-香茅醛 、 邻甲苯胺 在 4 A molecular sieve 作用下， 以 正戊烷 为溶剂， 生成 N-(R)-(3,7-Dimethyl-6-octenylidene)-o-toluidine
  参考文献：
  名称：

  Intramolecular hetero-Diels-Alder reaction of N-arylimines. Applications to the synthesis of octahydroacridine derivatives

  摘要：

  A new intramolecular Lewis acid catalyzed hetero-Diels-Alder reaction of N-arylimines 5 with nonactivated olefins tethered to the 2-azadiene system was developed in order to prepare 1,2,3,4,-4a,9,9a,10-octahydroacridine derivatives 6. Both reactivity and cis/trans selectivity of 6 were mainly dependent on the substitution pattern in the 3-position of the cyclization precursor 5. The type of Lewis acid plays only a minor role in determination of the cis/trans ratio. The synthetic utility of this new cyclization was increased by performing it as a one-pot reaction (3+4-->6). Both absolute configuration and preferred conformation were assigned by detailed NMR studies.

  DOI：

  10.1021/jo00062a033