1-[3-(4-Methoxyphenyl)prop-2-ynoxy]naphthalene | 1191065-32-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[3-(4-Methoxyphenyl)prop-2-ynoxy]naphthalene
• CAS: 1191065-32-3
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: UZQWDIWOCNXERG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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-[3-(4-Methoxyphenyl)prop-2-ynoxy]naphthalene 在 cesium fluoride 、 N,N-二乙基苯胺 作用下， 反应 0.5h， 以73%的产率得到3-(4-Methoxyphenyl)-2-methylbenzo[g][1]benzofuran
  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：

  萘酚 、 3-(4-甲氧基苯基)-2-丙炔-1-醇 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96%的产率得到1-[3-(4-Methoxyphenyl)prop-2-ynoxy]naphthalene
  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

文献信息

• Synthesis of Novel 3-Bromo-2H-chromene Derivatives: Palladium-Mediated Intramolecular Cyclization of Aryl Propargyl Ethers
  作者：Paramasivan Perumal、Gurunathan Savitha、Kulandhai Felix

  DOI：10.1055/s-0029-1217563

  日期：2009.8

  presence of catalytic amount of Pd(OAc) 2 in conjunction with stoichiometric amount of CuBr 2 and LiBr to the corresponding 3-bromo-2H-chromene derivatives in good yields. The protocol was further extended to synthesize 3-bromo-benzofused 2H-chromene derivatives.

  在催化量的 Pd(OAc) 2 以及化学计量量的 CuBr 2 和 LiBr 存在下，芳基炔丙基醚以良好的产率环化为相应的 3-溴-2H-色烯衍生物。该协议进一步扩展到合成 3-溴苯并稠合 2H-色烯衍生物。