2-benzyloxy-10-hydroxyundec-4-yn-6-one | 826994-56-3

• 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-10-hydroxyundec-4-yn-6-one
• 英文别名: 2-(Benzyloxy)-10-hydroxyundec-4-yn-6-one；10-hydroxy-2-phenylmethoxyundec-4-yn-6-one
• CAS: 826994-56-3
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: BBHPQSZVTOXBQM-UHFFFAOYSA-N

物化性质

• 沸点：
  425.6±55.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

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-10-hydroxyundec-4-yn-6-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 24.0h， 生成 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane 、 (+)-trans,trans-2,8-dimethyl-1,7-dioxaspiro<5.5>undecane 、 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane
  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：

  丁位己内酯 、 2-benzyloxypent-4-yne 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85%的产率得到2-benzyloxy-10-hydroxyundec-4-yn-6-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

• A convenient access to thermodynamically nonstabilised spiroketal isomers: the first synthesis of (Z)-7-methyl-1,6-dioxaspiro[4.5]decane
  作者：Jan Doubský、David Šaman、Jiří Zedník、Soňa Vašíčková、Bohumír Koutek

  DOI：10.1016/j.tetlet.2005.09.085

  日期：2005.11

  Functionalised hydroxy alpha-alkynones were transformed to the corresponding spiroketals by a one-pot cascade consisting of palladium-catalysed hydrogenation of the triple bond, hydroxyl group deprotection and spirocyclisation under mild nonacidic conditions. The reaction does not rely upon thermodynamic control to set the configuration of the ketal stereocentre so that both the anomerically stabilised and nonstabilised isomers are similarly accessible. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.