3-Decyn-1-yl ethyl ether | 150667-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Decyn-1-yl ethyl ether
• 英文别名: 1-Ethoxydec-3-yne
• CAS: 150667-82-6
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: RTPCRFHXNPXBGG-UHFFFAOYSA-N

物化性质

• 沸点：
  243.5±23.0 °C(predicted)
• 密度：
  0.842±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Decyn-1-yl ethyl ether 在 P-2 nickel 氢气 作用下， 生成 (Z)-3-Decen-1-yl ethyl ether
  参考文献：
  名称：

  Metal/ammonia reduction of ethers of 3-decyn-1-ol: effects of structure and conditions on cleavage and rearrangement

  摘要：

  Reduction of the THP, ethyl, tert-butyl and tert-butyldimethylsilyl (TBDMS) ethers of 3-decyn-1-ol with sodium in ammonia/THF results in extensive hydrogenolysis of the carbon-oxygen bond and concomitant bond migration, producing a mixture of 2- and 3-decenes and a very low yield of the desired (E)-homoallylic ether. Reduction in the presence of 2-methyl-2-propanol led to excellent yields of the desired (E)-3-decenol ethers. The 4- and 5-decyn-1-ol ethers were reduced normally to the (E)-decen-1-ol ethers except in the case of the TBDMS ethers which were cleaved to the (E)-alcohols under some of the reaction conditions.

  DOI：

  10.1021/jo00071a014
• 作为产物：
  描述：

  3-癸炔-1-醇 、 碘乙烷 在 sodium hydride 作用下， 以93%的产率得到3-Decyn-1-yl ethyl ether
  参考文献：
  名称：

  Metal/ammonia reduction of ethers of 3-decyn-1-ol: effects of structure and conditions on cleavage and rearrangement

  摘要：

  Reduction of the THP, ethyl, tert-butyl and tert-butyldimethylsilyl (TBDMS) ethers of 3-decyn-1-ol with sodium in ammonia/THF results in extensive hydrogenolysis of the carbon-oxygen bond and concomitant bond migration, producing a mixture of 2- and 3-decenes and a very low yield of the desired (E)-homoallylic ether. Reduction in the presence of 2-methyl-2-propanol led to excellent yields of the desired (E)-3-decenol ethers. The 4- and 5-decyn-1-ol ethers were reduced normally to the (E)-decen-1-ol ethers except in the case of the TBDMS ethers which were cleaved to the (E)-alcohols under some of the reaction conditions.

  DOI：

  10.1021/jo00071a014