1-[(Z)-4-(2-ethoxyethynyl)-3-ethyloct-3-en-1-ynyl]-2-methoxybenzene | 199165-29-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[(Z)-4-(2-ethoxyethynyl)-3-ethyloct-3-en-1-ynyl]-2-methoxybenzene
• CAS: 199165-29-2
• 化学式: C₂₁H₂₆O₂
• 分子量: 310.436
• InChiKey: ULDCYXYPQYXTIN-HNENSFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(Z)-4-(2-ethoxyethynyl)-3-ethyloct-3-en-1-ynyl]-2-methoxybenzene 以 氯苯 为溶剂， 反应 3.0h， 以28%的产率得到3-Butyl-4-ethyl-dibenzofuran-1-ol
  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-(bromoethynyl)-2-methoxybenzene 在 四(三苯基膦)钯 、 正丁基锂 、 zinc(II) chloride 作用下， 反应 12.08h， 生成 1-[(Z)-4-(2-ethoxyethynyl)-3-ethyloct-3-en-1-ynyl]-2-methoxybenzene
  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.