2-benzyloxy-8-hydroxyundec-3-yn-5-one | 826994-55-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-benzyloxy-8-hydroxyundec-3-yn-5-one
• 英文别名: 2-(Benzyloxy)-8-hydroxyundec-3-YN-5-one；8-hydroxy-2-phenylmethoxyundec-3-yn-5-one
• CAS: 826994-55-2
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: KKQOHKCWUMDONY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzyloxy-8-hydroxyundec-3-yn-5-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 37.0h， 以58%的产率得到2-methyl-7-propyl-1,6-dioxaspiro[4.4]nonane
  参考文献：
  名称：

  Alkynyltrifluoroborates as Versatile Tools in Organic Synthesis:  A New Route to Spiroketals

  摘要：

  A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl alpha-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/spirocyclization of the prespiroketal intermediate.

  DOI：

  10.1021/ol047987k
• 作为产物：
  描述：

  丙位庚内酯 、 ((but-3-yn-2-yloxy)methyl)benzene 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以79%的产率得到2-benzyloxy-8-hydroxyundec-3-yn-5-one
  参考文献：
  名称：

  Alkynyltrifluoroborates as Versatile Tools in Organic Synthesis:  A New Route to Spiroketals

  摘要：

  A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl alpha-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/spirocyclization of the prespiroketal intermediate.

  DOI：

  10.1021/ol047987k

文献信息

• Alkynyltrifluoroborates as Versatile Tools in Organic Synthesis:  A New Route to Spiroketals
  作者：Jan Doubský、Ludvík Streinz、David Šaman、Jiří Zedník、Bohumír Koutek

  DOI：10.1021/ol047987k

  日期：2004.12.1

  A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl alpha-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/spirocyclization of the prespiroketal intermediate.