(6E)-11-Methyl-6,11-dodecadien-2-ynal | 149798-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6E)-11-Methyl-6,11-dodecadien-2-ynal
• 英文别名: (6E)-11-methyldodeca-6,11-dien-2-ynal
• CAS: 149798-11-8
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: NXTCZYDJRSDCHI-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (6E)-11-Methyl-6,11-dodecadien-2-ynal 在 二氯乙基铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到(6E)-11-Methylene-6-cyclodecen-2-yn-1-ol
  参考文献：
  名称：

  Synthesis of 12-, 14-, and 16-membered propargylic alcohols through Lewis acid-promoted ene cyclization

  摘要：

  The scope of the Lewis acid-promoted ene cyclization has been expanded to include 12-, 14-, and 16-membered rings. Thus, the ynals 1.8, 2.5, and 3.5 undergo efficient type-I cyclization upon addition to 1.0 equiv of EtAlCl2 in CH2Cl2 at -78-degrees-C. The epoxy ynal 4.3 undergoes pinacol rearrangement under these conditions. However, treatment with a 1:1 mixture of Et2AlCl and EtAlCl2 effects conversion to the cyclic products 4.4/4.5 (92:8) in satisfactory yield. Facile type-II cyclizations readily achieved with ynals 5.7, 6.4, 7.6, and 8.3 with EtAlCl2 as the Lewis acid. In the latter case, a 16-membered propargylic alcohol was produced in 84% yield.

  DOI：

  10.1021/jo00067a024
• 作为产物：
  描述：

  5-甲基-5-己烯-1-醛 在 正丁基锂 、 TEA 、 二异丁基氢化铝 、 丙酸 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 (6E)-11-Methyl-6,11-dodecadien-2-ynal
  参考文献：
  名称：

  Synthesis of 12-, 14-, and 16-membered propargylic alcohols through Lewis acid-promoted ene cyclization

  摘要：

  The scope of the Lewis acid-promoted ene cyclization has been expanded to include 12-, 14-, and 16-membered rings. Thus, the ynals 1.8, 2.5, and 3.5 undergo efficient type-I cyclization upon addition to 1.0 equiv of EtAlCl2 in CH2Cl2 at -78-degrees-C. The epoxy ynal 4.3 undergoes pinacol rearrangement under these conditions. However, treatment with a 1:1 mixture of Et2AlCl and EtAlCl2 effects conversion to the cyclic products 4.4/4.5 (92:8) in satisfactory yield. Facile type-II cyclizations readily achieved with ynals 5.7, 6.4, 7.6, and 8.3 with EtAlCl2 as the Lewis acid. In the latter case, a 16-membered propargylic alcohol was produced in 84% yield.

  DOI：

  10.1021/jo00067a024

文献信息

• Synthesis of 12-, 14-, and 16-membered propargylic alcohols through Lewis acid-promoted ene cyclization
  作者：James A. Marshall、Marc W. Andersen

  DOI：10.1021/jo00067a024

  日期：1993.7

  The scope of the Lewis acid-promoted ene cyclization has been expanded to include 12-, 14-, and 16-membered rings. Thus, the ynals 1.8, 2.5, and 3.5 undergo efficient type-I cyclization upon addition to 1.0 equiv of EtAlCl2 in CH2Cl2 at -78-degrees-C. The epoxy ynal 4.3 undergoes pinacol rearrangement under these conditions. However, treatment with a 1:1 mixture of Et2AlCl and EtAlCl2 effects conversion to the cyclic products 4.4/4.5 (92:8) in satisfactory yield. Facile type-II cyclizations readily achieved with ynals 5.7, 6.4, 7.6, and 8.3 with EtAlCl2 as the Lewis acid. In the latter case, a 16-membered propargylic alcohol was produced in 84% yield.