3-methylhept-6-enoic acid benzylamide | 220445-71-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-methylhept-6-enoic acid benzylamide
• 英文别名: N-benzyl-3-methylhept-6-enamide
• CAS: 220445-71-6
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: SQQVUKCROBJEFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-methylhept-6-enoic acid benzylamide 在 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 2-diazo-N-benzyl-N-(3-methylhept-6-enoyl)malonamic acid ethyl ester
  参考文献：
  名称：

  Generation and Trapping of N-Acyliminium Ions Derived from Isomünchnone Cycloadducts. A Versatile Route to Functionalized Heterocycles

  摘要：

  A series of 2-diazo-N-hept-6-enoylmalonamides were prepared and treated with a catalytic amount of rhodium(II) perfluorobutyrate. The resultant carbenoids underwent facile cyclization onto the neighboring amide carbonyl oxygen atom to generate isomunchnone-type intermediates. Subsequent 1,3-dipolar cycloaddition across the pendant olefin afforded intramolecular cycloadducts in high yield. The cascade sequence is simple, direct, and extremely tolerant of structural diversity. Exposure of these cycloadducts to Lewis acids resulted in oxabicyclic ring opening. N-Acyliminium ions of wide structural variety can be easily generated by this sequence of reactions. Different cyclization pathways become available depending on the nature of the substituent group attached to the amide nitrogen. When the tethered group is electrophilic in nature, proton lass from the initially formed N-acyliminium ion occurs rapidly to-give an acyl enamide which undergoes a subsequent cyclization at the electrophilic center.

  DOI：

  10.1021/jo981624e
• 作为产物：
  描述：

  3-methylhept-6-enoic acid 、 苄胺 在 N,N'-羰基二咪唑 作用下， 生成 3-methylhept-6-enoic acid benzylamide
  参考文献：
  名称：

  Generation and Trapping of N-Acyliminium Ions Derived from Isomünchnone Cycloadducts. A Versatile Route to Functionalized Heterocycles

  摘要：

  A series of 2-diazo-N-hept-6-enoylmalonamides were prepared and treated with a catalytic amount of rhodium(II) perfluorobutyrate. The resultant carbenoids underwent facile cyclization onto the neighboring amide carbonyl oxygen atom to generate isomunchnone-type intermediates. Subsequent 1,3-dipolar cycloaddition across the pendant olefin afforded intramolecular cycloadducts in high yield. The cascade sequence is simple, direct, and extremely tolerant of structural diversity. Exposure of these cycloadducts to Lewis acids resulted in oxabicyclic ring opening. N-Acyliminium ions of wide structural variety can be easily generated by this sequence of reactions. Different cyclization pathways become available depending on the nature of the substituent group attached to the amide nitrogen. When the tethered group is electrophilic in nature, proton lass from the initially formed N-acyliminium ion occurs rapidly to-give an acyl enamide which undergoes a subsequent cyclization at the electrophilic center.

  DOI：

  10.1021/jo981624e