(Z)-3-butyl-1-ethoxy-4-ethyl-3-nonene-1,5-diyne | 199165-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-3-butyl-1-ethoxy-4-ethyl-3-nonene-1,5-diyne
• 英文别名: (Z)-7-(2-ethoxyethynyl)-6-ethylundec-6-en-4-yne
• CAS: 199165-25-8
• 化学式: C₁₇H₂₆O
• 分子量: 246.393
• InChiKey: LJCZSTZUPYBRRJ-MSUUIHNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 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)-3-butyl-1-ethoxy-4-ethyl-3-nonene-1,5-diyne 以 氯苯 为溶剂， 反应 3.0h， 以8%的产率得到5-butyl-4-ethyl-2-(2-propenyl)phenol
  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-己炔 在 四(三苯基膦)钯 、 正丁基锂 、 1,3-双(二苯基膦)丙烷 、 zinc(II) chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 反应 12.08h， 生成 (Z)-3-butyl-1-ethoxy-4-ethyl-3-nonene-1,5-diyne
  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

文献信息

• Synthesis and Thermolysis of Enediynyl Ethyl Ethers as Precursors of Enyne−Ketenes
  作者：Anna Tarli、Kung K. Wang

  DOI：10.1021/jo971391b

  日期：1997.12.1

  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.