2,3-undecadienamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: 2,3-undecadienamide
• 英文别名: undeca-2,3-dienamide
• 化学式: C₁₁H₁₉NO
• 分子量: 181.278
• InChiKey: BPZKUFHZMAPYGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  13.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.09
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,3-undecadienamide 在 copper(ll) bromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.0h， 以69%的产率得到4-bromo-5-(n-heptyl)-5-hydroxypyrrol-2(5H)-one
  参考文献：
  名称：

  Study on halolactamization-γ-hydroxylation or haloiminolactonization of 2,3-alkadienamides

  摘要：

  The reactions of 4-mono- or 4-unsubstituted 2,3-alkadienamides with CuX2 afforded 5-hydroxypyrTol-2(5H)-ones via the sequential lactamization and gamma-hydroxylation process in aqueous THF while those of 4,4-disubstituted 2,3-alkadienamides with CuX2 in THF afforded iminolactones in high yields. Iodoiminolactonization and iodolactamization/gamma-hydroxylation were achieved by the corresponding reaction with I-2 in THF at rt. The structures of the products depend on the steric hindrance at the 4-position of the starting allenamides. Relatively electron-rich allenes afforded the corresponding products in much higher yields under milder reaction conditions implying the intramolecular electrophilic nature of the cyclization reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.050
• 作为产物：
  描述：

  一氧化碳 、 3-bromo-1-decyne 在 四(三苯基膦)钯 氨 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、1.82 MPa 条件下， 反应 2.0h， 以68%的产率得到2,3-undecadienamide
  参考文献：
  名称：

  Study on halolactamization-γ-hydroxylation or haloiminolactonization of 2,3-alkadienamides

  摘要：

  The reactions of 4-mono- or 4-unsubstituted 2,3-alkadienamides with CuX2 afforded 5-hydroxypyrTol-2(5H)-ones via the sequential lactamization and gamma-hydroxylation process in aqueous THF while those of 4,4-disubstituted 2,3-alkadienamides with CuX2 in THF afforded iminolactones in high yields. Iodoiminolactonization and iodolactamization/gamma-hydroxylation were achieved by the corresponding reaction with I-2 in THF at rt. The structures of the products depend on the steric hindrance at the 4-position of the starting allenamides. Relatively electron-rich allenes afforded the corresponding products in much higher yields under milder reaction conditions implying the intramolecular electrophilic nature of the cyclization reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.050

文献信息

• Unexpected Facile Sequential Halolactamization−Hydroxylation of 2,3-Allenamides with CuX₂ for the Efficient Synthesis of 4-Halo-5-hydroxypyrrol-2(5<i>H</i>)-ones
  作者：Shengming Ma、Hexin Xie

  DOI：10.1021/ol006504j

  日期：2000.11.1

  [GRAPHICS]4-Halo-5-hydroxypyrrol-2(5H)-ones were synthesized from the efficient sequential halolactamization-hydroxylation reaction of 4-monosubstituted 2,3-allenamides with CuX2 (X = Br, CI) in high yields. Halolactamization of fully substituted 2,3-dienamide (1f) afforded 4-halo-pyrrol-2(5H)-ones.
• Study on halolactamization-γ-hydroxylation or haloiminolactonization of 2,3-alkadienamides
  作者：Shengming Ma、Hexin Xie

  DOI：10.1016/j.tet.2004.10.050

  日期：2005.1

  The reactions of 4-mono- or 4-unsubstituted 2,3-alkadienamides with CuX2 afforded 5-hydroxypyrTol-2(5H)-ones via the sequential lactamization and gamma-hydroxylation process in aqueous THF while those of 4,4-disubstituted 2,3-alkadienamides with CuX2 in THF afforded iminolactones in high yields. Iodoiminolactonization and iodolactamization/gamma-hydroxylation were achieved by the corresponding reaction with I-2 in THF at rt. The structures of the products depend on the steric hindrance at the 4-position of the starting allenamides. Relatively electron-rich allenes afforded the corresponding products in much higher yields under milder reaction conditions implying the intramolecular electrophilic nature of the cyclization reaction. (C) 2004 Elsevier Ltd. All rights reserved.