8-(2-tetrahydropyranyloxy)oct-5-yn-2-one | 1379038-75-1

• 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: 8-(2-tetrahydropyranyloxy)oct-5-yn-2-one
• CAS: 1379038-75-1
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: KWIRWJULYHDSKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-(2-tetrahydropyranyloxy)oct-5-yn-2-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 四溴化碳 、 dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-3-yl)phosphine 、 sodium hexamethyldisilazane 、 sodium hydride 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.83h， 生成 dimethyl 2-(3-methylbut-3-enyl)-3-phenyl-2-cyclopentene-1,1-dicarboxylate
  参考文献：
  名称：

  Synthesis of 1,2-Disubstituted Cyclopentenes by Palladium-Catalyzed Reaction of Homopropargyl-Substituted Dicarbonyl Compounds with Organic Halides via 5-Endo-Dig Cyclization

  摘要：

  Palladium catalysts with bulky biaryl phosphine ligands allow homopropargyl-substituted dicarbonyl compounds to undergo intramolecular addition via a rare 5-endo-dig pathway. C-C bond forming reductive elimination follows the addition to Introduce alkenyl and alkynyl as well as aryl groups by using the corresponding organic halides. The cyclization is versatile enough to be applicable to the synthesis of highly substituted dihydropyrrole and a fused tricyclic compound.

  DOI：

  10.1021/ol301257m
• 作为产物：
  描述：

  2-(3-丁炔氧基)四水-2H-吡喃 、 丁烯酮 在 四氢吡咯 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 作用下， 以 苯 为溶剂， 反应 12.0h， 以63%的产率得到8-(2-tetrahydropyranyloxy)oct-5-yn-2-one
  参考文献：
  名称：

  Synthesis of 1,2-Disubstituted Cyclopentenes by Palladium-Catalyzed Reaction of Homopropargyl-Substituted Dicarbonyl Compounds with Organic Halides via 5-Endo-Dig Cyclization

  摘要：

  Palladium catalysts with bulky biaryl phosphine ligands allow homopropargyl-substituted dicarbonyl compounds to undergo intramolecular addition via a rare 5-endo-dig pathway. C-C bond forming reductive elimination follows the addition to Introduce alkenyl and alkynyl as well as aryl groups by using the corresponding organic halides. The cyclization is versatile enough to be applicable to the synthesis of highly substituted dihydropyrrole and a fused tricyclic compound.

  DOI：

  10.1021/ol301257m