4-methylenenon-8-yn-1-ol | 917989-35-6

• 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: 4-methylenenon-8-yn-1-ol
• 英文别名: 4-Methylidenenon-8-YN-1-OL；4-methylidenenon-8-yn-1-ol
• CAS: 917989-35-6
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: GBJRFSJQGDMMHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  4-methylenenon-8-yn-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以73%的产率得到4-methylenenon-8-ynal
  参考文献：
  名称：

  An approach to triquinane synthesis using the Pauson–Khand reaction

  摘要：

  Tricyclic skeletons have been generated from acyclic enyne precursors by using an intramolecular Pauson-Khand reaction in combination with aldol, Michael and alkylation reactions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.022
• 作为产物：
  描述：

  5-溴戊-1-炔基(三甲基)硅烷 在 正丁基锂 、 四丁基氟化铵 、 magnesium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 96.5h， 生成 4-methylenenon-8-yn-1-ol
  参考文献：
  名称：

  Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry

  摘要：

  Biologically active alpha-methylenene propellanone has been synthesised in 12 steps in an overall yield of 11%. The key step of the synthesis, an intramolecular Pauson-Khand reaction, proceeds in good yield under alkyl sulfide promotion conditions, to furnish the 5,5-fused moiety within the target Samarium diiodide-induced intramolecular conjugate addition onto the resulting cyclopentenone was used to complete the intriguing [3.3.3] propellanone skeleton. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.003

文献信息

• Synthesis of α-methylene propellanone via the strategic employment of metal-mediated cyclisation chemistry
  作者：William J. Kerr、Angus J. Morrison、Laura C. Paterson

  DOI：10.1016/j.tet.2015.06.003

  日期：2015.8

  Biologically active alpha-methylenene propellanone has been synthesised in 12 steps in an overall yield of 11%. The key step of the synthesis, an intramolecular Pauson-Khand reaction, proceeds in good yield under alkyl sulfide promotion conditions, to furnish the 5,5-fused moiety within the target Samarium diiodide-induced intramolecular conjugate addition onto the resulting cyclopentenone was used to complete the intriguing [3.3.3] propellanone skeleton. (C) 2015 Elsevier Ltd. All rights reserved.
• An approach to triquinane synthesis using the Pauson–Khand reaction
  作者：Marie E. Krafft、Graham M. Kyne、Chitaru Hirosawa、Peter Schmidt、Khalil A. Abboud、Nathalie L'Helias

  DOI：10.1016/j.tet.2006.09.022

  日期：2006.12

  Tricyclic skeletons have been generated from acyclic enyne precursors by using an intramolecular Pauson-Khand reaction in combination with aldol, Michael and alkylation reactions. (c) 2006 Elsevier Ltd. All rights reserved.