2-(2,6-cyclooctadienyl)-1-ethanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,6-cyclooctadienyl)-1-ethanol
• 英文别名: 2-[(2Z,6Z)-cycloocta-2,6-dien-1-yl]ethanol
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: WHGQBIQSWPJUJQ-ILNZVKDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  2-(2,6-cyclooctadienyl)-1-ethanol 在 吡啶 、 对甲苯磺酰氯 、 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 、 乙醚 为溶剂， 反应 8.0h， 以61%的产率得到(1Z,5Z)-3-Ethyl-cycloocta-1,5-diene
  参考文献：
  名称：

  PS-COD and PS-9-BBN:  Polymer-Supported Reagents for Solution-Phase Parallel Synthesis

  摘要：

  1,5-Cyclooctadiene was deprotonated under LICKOR conditions and reacted with Merrifield resin to afford an immobilized cyclooctadiene in high yield. This polymer is effective as a halogen scavenger, while hydroboration leads to a supported 9-BBN analogue. The latter exhibits similar regioselectivity to 9-BBN in olefin hydroboration.

  DOI：

  10.1021/ol047458g
• 作为产物：
  描述：

  环氧乙烷 、 1,5-cis,cis-cyclooctadiene 在 potassium tert-butylate 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以62%的产率得到2-(2,6-cyclooctadienyl)-1-ethanol
  参考文献：
  名称：

  Synthesis of Functionalized 1,5-Cyclooctadienes by LICKOR Metalation

  摘要：

  1,5-Cyclooctadiene was lithiated under LICKOR superbase conditions followed by reaction with alkyl halides or ethylene oxide to yield 3-substituted 1,5-cyclooetadienes in high yield and purity. This procedure is suitable for preparation of 1,5-cyclooctadienes carrying pendant functional groups for immobilization on solid-phase resins.

  DOI：

  10.1021/jo025715u

文献信息

• PS-COD and PS-9-BBN:  Polymer-Supported Reagents for Solution-Phase Parallel Synthesis
  作者：Jefferson D. Revell、Barbara Dörner、Peter D. White、A. Ganesan

  DOI：10.1021/ol047458g

  日期：2005.3.1

  1,5-Cyclooctadiene was deprotonated under LICKOR conditions and reacted with Merrifield resin to afford an immobilized cyclooctadiene in high yield. This polymer is effective as a halogen scavenger, while hydroboration leads to a supported 9-BBN analogue. The latter exhibits similar regioselectivity to 9-BBN in olefin hydroboration.
• Synthesis of Functionalized 1,5-Cyclooctadienes by LICKOR Metalation
  作者：Jefferson D. Revell、A. Ganesan

  DOI：10.1021/jo025715u

  日期：2002.8.1

  1,5-Cyclooctadiene was lithiated under LICKOR superbase conditions followed by reaction with alkyl halides or ethylene oxide to yield 3-substituted 1,5-cyclooetadienes in high yield and purity. This procedure is suitable for preparation of 1,5-cyclooctadienes carrying pendant functional groups for immobilization on solid-phase resins.