(Z)-5-(2-ethoxyethynyl)-6-ethyldodec-5-en-7-yne | 199165-26-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-5-(2-ethoxyethynyl)-6-ethyldodec-5-en-7-yne
• CAS: 199165-26-9
• 化学式: C₁₈H₂₈O
• 分子量: 260.42
• InChiKey: PDKARLJEQSXURB-ZCXUNETKSA-N

物化性质

• 沸点：
  348.8±34.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (Z)-5-(2-ethoxyethynyl)-6-ethyldodec-5-en-7-yne 以 氯苯 为溶剂， 反应 3.0h， 以23%的产率得到7-Butyl-6-ethyl-2-methyl-chroman
  参考文献：
  名称：

  Synthesis and Thermolysis of Enediynyl Ethyl Ethers as Precursors of Enyne−Ketenes

  摘要：

  Enediynyl ethyl ethers 14/17 were synthesized by using the Pd(PPh3)(4)-catalyzed cross-coupling reactions between enynyl iodides 13/16 and (2-ethoxyethynyl)zinc chloride. Thermolysis of these enediynyl ethyl ethers in refluxing chlorobenzene (132 degrees C) promoted a retro-ene reaction to produce enyne-ketenes, which underwent the Moore cyclization reactions to form the biradicals having a phenyl radical center and a phenoxy radical center. The presence of two radical centers in the same molecule simultaneously provided many opportunities for intramolecular decay through disproportionation, radical-radical combination, and the formation of o-quinone methide.

  DOI：

  10.1021/jo971391b
• 作为产物：
  描述：

  1-bromohexyne 在 四(三苯基膦)钯 、 正丁基锂 、 zinc(II) chloride 作用下， 反应 12.08h， 生成 (Z)-5-(2-ethoxyethynyl)-6-ethyldodec-5-en-7-yne
  参考文献：
  名称：

  Synthesis and Thermolysis of Enediynyl Ethyl Ethers as Precursors of Enyne−Ketenes

  摘要：

  Enediynyl ethyl ethers 14/17 were synthesized by using the Pd(PPh3)(4)-catalyzed cross-coupling reactions between enynyl iodides 13/16 and (2-ethoxyethynyl)zinc chloride. Thermolysis of these enediynyl ethyl ethers in refluxing chlorobenzene (132 degrees C) promoted a retro-ene reaction to produce enyne-ketenes, which underwent the Moore cyclization reactions to form the biradicals having a phenyl radical center and a phenoxy radical center. The presence of two radical centers in the same molecule simultaneously provided many opportunities for intramolecular decay through disproportionation, radical-radical combination, and the formation of o-quinone methide.

  DOI：

  10.1021/jo971391b