1-Phenyl-6-<(tetrahydro-2H-pyran-2-yl)oxy>-1-hexyn-3-one | 155193-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1-Phenyl-6-<(tetrahydro-2H-pyran-2-yl)oxy>-1-hexyn-3-one
• 英文别名: 1-phenyl-6-((tetrahydro-2H-pyran-2-yl)oxy)hex-1-yn-3-one；6-(Oxan-2-yloxy)-1-phenylhex-1-yn-3-one
• CAS: 155193-03-6
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: GIBMNAKSAJAFNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-Phenyl-6-<(tetrahydro-2H-pyran-2-yl)oxy>-1-hexyn-3-one 、 甲基锂 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 以84%的产率得到3-Methyl-1-phenyl-6-<(tetrahydro-2H-pyran-2-yl)oxy>-1-hexyn-3-ol
  参考文献：
  名称：

  Formation of Angularly-Fused Triquinanes by Successive Use of the Pauson-Khand Reaction and Radical Closure

  摘要：

  Angularly-fused triquinanes (see Table 1) are accessible by sequential use of the Pauson-Khand reaction and radical cyclization. The Pauson-Khand step works in the presence of homolyzable bonds, such as C-Br and C-SePh. The method seems best suited to the preparation of triquinanes containing heteroatoms, as the starting materials are then easily made. In one case the radical closure step (15 --> 16 and 17) generated two five-membered rings fused in a trans manner; this stereochemistry was confirmed by X-ray analysis of the crystalline product.

  DOI：

  10.1021/jo00085a032
• 作为产物：
  描述：

  4-四氢吡喃基氧基-丁烷-1-醇 在 正丁基锂 、 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 1-Phenyl-6-<(tetrahydro-2H-pyran-2-yl)oxy>-1-hexyn-3-one
  参考文献：
  名称：

  Au-catalyzed intramolecular hydroalkoxylation of gem-difluorinated alkynols

  摘要：

  The intramolecular hydroalkoxylation of gem-difluorinated alkynols was found possible under Au catalysis, allowing for the preparation of a series of fluorinated heterocycles. The nature of the solvent was found to be especially critical in the cyclization of gem-difluorohomopropargylic alcohols as it dictated whether the resulting 2,3-dihydrofuran underwent subsequent aromatization to the corresponding furan or not.

  DOI：

  10.1016/j.jfluchem.2018.09.009

文献信息

• Clive Derrick L. J., Cole Derek C., Tao Yong, J. Org. Chem, 59 (1994) N 6, S 1396-1406
  作者：Clive Derrick L. J., Cole Derek C., Tao Yong

  DOI：——

  日期：——
• Au-catalyzed intramolecular hydroalkoxylation of gem-difluorinated alkynols
  作者：Jean-Denys Hamel、Jean-François Paquin

  DOI：10.1016/j.jfluchem.2018.09.009

  日期：2018.12

  The intramolecular hydroalkoxylation of gem-difluorinated alkynols was found possible under Au catalysis, allowing for the preparation of a series of fluorinated heterocycles. The nature of the solvent was found to be especially critical in the cyclization of gem-difluorohomopropargylic alcohols as it dictated whether the resulting 2,3-dihydrofuran underwent subsequent aromatization to the corresponding furan or not.
• Formation of Angularly-Fused Triquinanes by Successive Use of the Pauson-Khand Reaction and Radical Closure
  作者：Derrick L. J. Clive、Derek C. Cole、Yong Tao

  DOI：10.1021/jo00085a032

  日期：1994.3

  Angularly-fused triquinanes (see Table 1) are accessible by sequential use of the Pauson-Khand reaction and radical cyclization. The Pauson-Khand step works in the presence of homolyzable bonds, such as C-Br and C-SePh. The method seems best suited to the preparation of triquinanes containing heteroatoms, as the starting materials are then easily made. In one case the radical closure step (15 --> 16 and 17) generated two five-membered rings fused in a trans manner; this stereochemistry was confirmed by X-ray analysis of the crystalline product.