3-[3-(naphthalene-1-yloxy)prop-1-yn-1-yl]pyridine | 1402044-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-[3-(naphthalene-1-yloxy)prop-1-yn-1-yl]pyridine
• CAS: 1402044-20-5
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: HODWTIVFLNVBAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-[3-(naphthalene-1-yloxy)prop-1-yn-1-yl]pyridine 在 cesium fluoride 、 N,N-二乙基苯胺 作用下， 反应 0.75h， 以52%的产率得到3-(2-methylnaphtho[1,2-b]furan-3-yl)pyridine
  参考文献：
  名称：

  Microwave-assisted Claisen rearrangement of naphthyl 2-propynyl ethers: synthesis of naphthofurans

  摘要：

  An efficient two-step approach for the synthesis of naphtho[1,2-b]furans and naphtho[2,1-b]furans has been developed. Various functionalized propargyl alcohols were etherified with alpha- or beta-naphthol under Mitsunobu reaction conditions to give naphthyl 2-propynyl ethers, which underwent a facile microwave-assisted Claisen rearrangement and concomitant anionic cyclization to yield naphthofuran derivatives under basic reaction conditions. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.053
• 作为产物：
  描述：

  3-(3-吡啶基)-2-丙炔-1-醇 、 萘酚 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到3-[3-(naphthalene-1-yloxy)prop-1-yn-1-yl]pyridine
  参考文献：
  名称：

  Microwave-assisted Claisen rearrangement of naphthyl 2-propynyl ethers: synthesis of naphthofurans

  摘要：

  An efficient two-step approach for the synthesis of naphtho[1,2-b]furans and naphtho[2,1-b]furans has been developed. Various functionalized propargyl alcohols were etherified with alpha- or beta-naphthol under Mitsunobu reaction conditions to give naphthyl 2-propynyl ethers, which underwent a facile microwave-assisted Claisen rearrangement and concomitant anionic cyclization to yield naphthofuran derivatives under basic reaction conditions. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.053