1-(4-n-hexyloxyphenyl)-2-(4'-hydroxyphenyl)acetylene | 50353-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-n-hexyloxyphenyl)-2-(4'-hydroxyphenyl)acetylene
• 英文别名: 4-[2-(4-Hexoxyphenyl)ethynyl]phenol；4-[2-(4-hexoxyphenyl)ethynyl]phenol
• CAS: 50353-64-5
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: FWMAPOBFRHXMET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-正己氧基溴苯 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 1-(4-n-hexyloxyphenyl)-2-(4'-hydroxyphenyl)acetylene
  参考文献：
  名称：

  Phenoxide-mediated Sonogashira coupling of trimethylsilylalkynes and aryliodides: practical synthesis of phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes

  摘要：

  We successfully synthesized phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes from trimethylsilylalkynes and aryliodides via silyl-group-migration-induced deprotection of alkynes and the usual Sonogashira coupling. The phenol moiety, which works as a desilylating agent, can be attached to any position in the coupling partner. This improvement for Sonogashira coupling would be highly effective, especially when the coupling partner has a phenol moiety. Additionally, the stability of the migrated silyl moiety on the ethynylation of 2-iodophenol is discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.01.091

文献信息

• Pugh, C.; Taernstroem, C.; Percec, V., Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 195, p. 185 - 197
  作者：Pugh, C.、Taernstroem, C.、Percec, V.

  DOI：——

  日期：——
• Phenoxide-mediated Sonogashira coupling of trimethylsilylalkynes and aryliodides: practical synthesis of phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes
  作者：Masayuki Shigeta、Junji Watanabe、Gen-ichi Konishi

  DOI：10.1016/j.tetlet.2013.01.091

  日期：2013.3

  We successfully synthesized phenolic-hydroxy-substituted diarylethynes and 1,4-diarylbutadiynes from trimethylsilylalkynes and aryliodides via silyl-group-migration-induced deprotection of alkynes and the usual Sonogashira coupling. The phenol moiety, which works as a desilylating agent, can be attached to any position in the coupling partner. This improvement for Sonogashira coupling would be highly effective, especially when the coupling partner has a phenol moiety. Additionally, the stability of the migrated silyl moiety on the ethynylation of 2-iodophenol is discussed. (C) 2013 Elsevier Ltd. All rights reserved.