2-methylnona-3,4-dien-2-ol | 33564-17-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methylnona-3,4-dien-2-ol
• CAS: 33564-17-9
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: XBUUMLBUJFVERF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methylnona-3,4-dien-2-ol 、 3-溴丙烯 在 palladium dichloride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以57%的产率得到5-butyl-2,2-dimethyl-4-(2'-propenyl)-2,5-dihydrofuran
  参考文献：
  名称：

  Efficient Synthesis of 4-(2‘-Alkenyl)-2,5-dihydrofurans and 5,6-Dihydro-2H-pyrans via the Pd-Catalyzed Cyclizative Coupling Reaction of 2,3- or 3,4-Allenols with Allylic Halides

  摘要：

  In the absence of a base, palladium(II) catalysts, such as PdCl2, PdCl2(CH3CN)(2), Pd(OAc)(2), and [(pi-C3H5)PdCl](2), can catalyze the cyclizative coupling reaction of 2,3- or 3,4-allenols with allylic halides in DMA at room temperature to provide 2,5-dihydrofurans and 5,6-dihydro-2H-pyrans, respectively, in moderate to good yields. Under similar reaction conditions, nonsubstituted 2,3-allenol 1s affords bimolecular cyclizative coupling product 5s as the major product. The scope of the reaction and its mechanism have been studied briefly. On the basis of the experimental results, the transformation was believed to proceed via a divalent palladium-catalyzed pathway.

  DOI：

  10.1021/jo0163997
• 作为产物：
  描述：

  2-methyl-5-(tetrahydropyran-2-yloxy)non-3-yn-2-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以58%的产率得到2-methylnona-3,4-dien-2-ol
  参考文献：
  名称：

  Efficient Synthesis of 4-(2‘-Alkenyl)-2,5-dihydrofurans and 5,6-Dihydro-2H-pyrans via the Pd-Catalyzed Cyclizative Coupling Reaction of 2,3- or 3,4-Allenols with Allylic Halides

  摘要：

  In the absence of a base, palladium(II) catalysts, such as PdCl2, PdCl2(CH3CN)(2), Pd(OAc)(2), and [(pi-C3H5)PdCl](2), can catalyze the cyclizative coupling reaction of 2,3- or 3,4-allenols with allylic halides in DMA at room temperature to provide 2,5-dihydrofurans and 5,6-dihydro-2H-pyrans, respectively, in moderate to good yields. Under similar reaction conditions, nonsubstituted 2,3-allenol 1s affords bimolecular cyclizative coupling product 5s as the major product. The scope of the reaction and its mechanism have been studied briefly. On the basis of the experimental results, the transformation was believed to proceed via a divalent palladium-catalyzed pathway.

  DOI：

  10.1021/jo0163997

文献信息

• Efficient Synthesis of 4-(2‘-Alkenyl)-2,5-dihydrofurans and 5,6-Dihydro-2<i>H</i>-pyrans via the Pd-Catalyzed Cyclizative Coupling Reaction of 2,3- or 3,4-Allenols with Allylic Halides
  作者：Shengming Ma、Wenzhong Gao

  DOI：10.1021/jo0163997

  日期：2002.8.1

  In the absence of a base, palladium(II) catalysts, such as PdCl2, PdCl2(CH3CN)(2), Pd(OAc)(2), and [(pi-C3H5)PdCl](2), can catalyze the cyclizative coupling reaction of 2,3- or 3,4-allenols with allylic halides in DMA at room temperature to provide 2,5-dihydrofurans and 5,6-dihydro-2H-pyrans, respectively, in moderate to good yields. Under similar reaction conditions, nonsubstituted 2,3-allenol 1s affords bimolecular cyclizative coupling product 5s as the major product. The scope of the reaction and its mechanism have been studied briefly. On the basis of the experimental results, the transformation was believed to proceed via a divalent palladium-catalyzed pathway.