3,5-bis(ethynyl)-1-(hept-1-yloxyl)benzene | 640297-88-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(ethynyl)-1-(hept-1-yloxyl)benzene
• 英文别名: 1,3-Diethynyl-5-(heptyloxy)benzene；1,3-diethynyl-5-heptoxybenzene
• CAS: 640297-88-7
• 化学式: C₁₇H₂₀O
• 分子量: 240.345
• InChiKey: KQKXSMYMKTZUEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  3,8-二溴菲罗啉 、 3,5-bis(ethynyl)-1-(hept-1-yloxyl)benzene 在 lithium hexamethyldisilazane 、 9-METHOXY-9-BORABICYCLO[3.3.1]NONANE 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 26.5h， 以74%的产率得到3,8-bis(3-ethynyl-5-(hept-1-yloxy)phenylethynyl)-1,10-phenanthroline
  参考文献：
  名称：

  Coupling of 3,8-Dibromo-1,10-phenanthroline with 3,5-Diethynylheptyloxybenzene: A Suzuki/Miyaura Versus a Sonogashira Perspective

  摘要：

  We report a new application of the Suzuki-Miyaura reaction whereas two bifunctional reactants, 3,8-dibromo-1,10-phenanthroline and 3,5-diethynylheptyloxylbenzene (9), yield 3,8-bis(3-ethynyl-5-heptyloxyphenylethynyl)-1,10-phenanthroline (2) efficiently (74% yield) without polymerization. This was achieved by reacting a stoichiometric amount of 9 and (Me3Si)(2)NLi to obtain quantitatively the monoacetylide anion of 9 (10). The latter was activated with B-methoxy-9-BBN and reacted in analogy to the alkynyl copper complex of a Sonogashira route. However, in the Sonogashira reaction, the alkynyl copper complex is present in small equilibrium concentrations and polymerization takes place even when reagents are mixed slowly. Actually the Sonogashira route gave no desired product 2, as the latter polymerizes easily via homo-coupling in the presence of air and Cu(I).

  DOI：

  10.1081/scc-120023989
• 作为产物：
  描述：

  3,5-bis(trimethylsilylethynyl)-1-(hept-1-yloxyl)benzene 在 sodium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 2.0h， 以98%的产率得到3,5-bis(ethynyl)-1-(hept-1-yloxyl)benzene
  参考文献：
  名称：

  Coupling of 3,8-Dibromo-1,10-phenanthroline with 3,5-Diethynylheptyloxybenzene: A Suzuki/Miyaura Versus a Sonogashira Perspective

  摘要：

  We report a new application of the Suzuki-Miyaura reaction whereas two bifunctional reactants, 3,8-dibromo-1,10-phenanthroline and 3,5-diethynylheptyloxylbenzene (9), yield 3,8-bis(3-ethynyl-5-heptyloxyphenylethynyl)-1,10-phenanthroline (2) efficiently (74% yield) without polymerization. This was achieved by reacting a stoichiometric amount of 9 and (Me3Si)(2)NLi to obtain quantitatively the monoacetylide anion of 9 (10). The latter was activated with B-methoxy-9-BBN and reacted in analogy to the alkynyl copper complex of a Sonogashira route. However, in the Sonogashira reaction, the alkynyl copper complex is present in small equilibrium concentrations and polymerization takes place even when reagents are mixed slowly. Actually the Sonogashira route gave no desired product 2, as the latter polymerizes easily via homo-coupling in the presence of air and Cu(I).

  DOI：

  10.1081/scc-120023989

文献信息

• Coupling of 3,8-Dibromo-1,10-phenanthroline with 3,5-Diethynylheptyloxybenzene: A Suzuki/Miyaura Versus a Sonogashira Perspective
  作者：Yang, Jinhua、Oh, Woon Su、Elder, Ian A.、Leventis, Nicholas、Sotiriou-Leventis, Chariklia

  DOI：10.1081/scc-120023989

  日期：2003.9

  We report a new application of the Suzuki-Miyaura reaction whereas two bifunctional reactants, 3,8-dibromo-1,10-phenanthroline and 3,5-diethynylheptyloxylbenzene (9), yield 3,8-bis(3-ethynyl-5-heptyloxyphenylethynyl)-1,10-phenanthroline (2) efficiently (74% yield) without polymerization. This was achieved by reacting a stoichiometric amount of 9 and (Me3Si)(2)NLi to obtain quantitatively the monoacetylide anion of 9 (10). The latter was activated with B-methoxy-9-BBN and reacted in analogy to the alkynyl copper complex of a Sonogashira route. However, in the Sonogashira reaction, the alkynyl copper complex is present in small equilibrium concentrations and polymerization takes place even when reagents are mixed slowly. Actually the Sonogashira route gave no desired product 2, as the latter polymerizes easily via homo-coupling in the presence of air and Cu(I).