2-(3-Methylpent-1-en-4-yn-3-yloxy)ethanol | 214967-58-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-Methylpent-1-en-4-yn-3-yloxy)ethanol
• 英文别名: 2-(3-methylpent-1-en-4-yn-3-yloxy)ethanol
• CAS: 214967-58-5
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: IHNDFFIPYINVMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-Methylpent-1-en-4-yn-3-yloxy)ethanol 在 盐酸 、 potassium tert-butylate 、 水 作用下， 生成 3-methyl-penta-2,4-dienal
  参考文献：
  名称：

  A Novel Aldol Condensation Alternative:α,β-Unsaturated Aldehydes from 3-Hydroxy-1-alkynes via Dihydrodioxepins

  摘要：

  The controlled aldol condensation between an aliphatic ketone and an acetaldehyde equivalent remains a challenge. One solution to this evergreen problem consists of the nucleophilic addition of acetylene to the ketone and the subsequent isomerization of the resulting 3-hydroxy-1-alkyne to the corresponding 2-alkenal. So far, however, the latter step could only be executed with acid-insensitive substrates. We now present a milder, three-step method which extends the scope of the procedure considerably. In the first step, the 3-hydroxy-1-alkynes are converted into 2-propynyl ethylene glycol monoethers; these then undergo base-catalyzed cyclization to give the dihydro-1,4-dioxepins, which are hydrolyzed in acidic medium in the third and final step.

  DOI：

  10.1002/(sici)1521-3765(19980904)4:9<1738::aid-chem1738>3.0.co;2-p
• 作为产物：
  描述：

  亚硫酸亚乙酯 、 3-甲基-1-戊烯-4-炔-3-醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以60%的产率得到2-(3-Methylpent-1-en-4-yn-3-yloxy)ethanol
  参考文献：
  名称：

  A Novel Aldol Condensation Alternative:α,β-Unsaturated Aldehydes from 3-Hydroxy-1-alkynes via Dihydrodioxepins

  摘要：

  The controlled aldol condensation between an aliphatic ketone and an acetaldehyde equivalent remains a challenge. One solution to this evergreen problem consists of the nucleophilic addition of acetylene to the ketone and the subsequent isomerization of the resulting 3-hydroxy-1-alkyne to the corresponding 2-alkenal. So far, however, the latter step could only be executed with acid-insensitive substrates. We now present a milder, three-step method which extends the scope of the procedure considerably. In the first step, the 3-hydroxy-1-alkynes are converted into 2-propynyl ethylene glycol monoethers; these then undergo base-catalyzed cyclization to give the dihydro-1,4-dioxepins, which are hydrolyzed in acidic medium in the third and final step.

  DOI：

  10.1002/(sici)1521-3765(19980904)4:9<1738::aid-chem1738>3.0.co;2-p

文献信息

• A Novel Aldol Condensation Alternative:α,β-Unsaturated Aldehydes from 3-Hydroxy-1-alkynes via Dihydrodioxepins
  作者：Heng-xu Wei、Manfred Schlosser

  DOI：10.1002/(sici)1521-3765(19980904)4:9<1738::aid-chem1738>3.0.co;2-p

  日期：1998.9.4

  The controlled aldol condensation between an aliphatic ketone and an acetaldehyde equivalent remains a challenge. One solution to this evergreen problem consists of the nucleophilic addition of acetylene to the ketone and the subsequent isomerization of the resulting 3-hydroxy-1-alkyne to the corresponding 2-alkenal. So far, however, the latter step could only be executed with acid-insensitive substrates. We now present a milder, three-step method which extends the scope of the procedure considerably. In the first step, the 3-hydroxy-1-alkynes are converted into 2-propynyl ethylene glycol monoethers; these then undergo base-catalyzed cyclization to give the dihydro-1,4-dioxepins, which are hydrolyzed in acidic medium in the third and final step.