benzyl 2-[2'-(p-methoxyphenyl)ethynyl]phenyl ether | 1170723-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: benzyl 2-[2'-(p-methoxyphenyl)ethynyl]phenyl ether
• 英文别名: 1-Methoxy-4-[2-(2-phenylmethoxyphenyl)ethynyl]benzene；1-methoxy-4-[2-(2-phenylmethoxyphenyl)ethynyl]benzene
• CAS: 1170723-95-1
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: KOMQRDBGRABELQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  benzyl 2-[2'-(p-methoxyphenyl)ethynyl]phenyl ether 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以62%的产率得到2-(4-甲氧基苯基)苯并呋喃
  参考文献：
  名称：

  p-Toluenesulfonic acid-mediated cyclization of o-(1-alkynyl)anisoles or thioanisoles: synthesis of 2-arylsubstituted benzofurans and benzothiophenes

  摘要：

  A variety of 2-arylbenzo[b]furans are readily prepared in good to excellent yields from the cyclization of o-(1-alkynyl)anisole derivatives under mild reaction conditions using an alcoholic media, p-toluenesulfonic acid under microwave irradiation. Starting from the corresponding o-(1-alkynyl)thioanisole derivatives, this friendly and environmentally free-metal procedure has been successfully extended to the synthesis of benzo[b]thiophenes. Relative to the electronic nature of the substituents, the selectivity of the cyclization reaction from differently o,o'-substituted diarylalkynes is also discussed. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.03.087
• 作为产物：
  描述：

  1-(苄氧基)-2-碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 benzyl 2-[2'-(p-methoxyphenyl)ethynyl]phenyl ether
  参考文献：
  名称：

  在强布朗斯台德碱的自动串联催化下，通过分子内/分子间加成序列合成二芳基烷烃。

  摘要：

  具有强布朗斯台德碱的自动串联催化能够合成含有苯并呋喃部分的二芳基烷烃。钾叔丁醇催化效率两者的分子内环化较少酸性邻-alkynylaryl苄基醚和以下的分子间加成二芳到苯乙烯，表明在有机合成中催化的高电位。

  DOI：

  10.1039/d0cc04512h

文献信息

• Phosphazene base-catalyzed intramolecular cyclization for efficient synthesis of benzofurans via carbon–carbon bond formation
  作者：Chikashi Kanazawa、Kengo Goto、Masahiro Terada

  DOI：10.1039/b913588j

  日期：——

  An organic superbase, phosphazene P4-(t)Bu, functioned as an active catalyst for intramolecular cyclization of o-alkynylphenyl ethers via carbon-carbon bond formation to provide an efficient synthetic method for 2,3-disubstituted benzofurans derivatives under mild reaction conditions without the need for a metal catalyst.

  有机超碱磷腈P4-（t）Bu用作通过碳-碳键形成邻炔基苯基醚分子内环化的活性催化剂，为2,3-二取代苯并呋喃衍生物的温和反应条件提供了一种有效的合成方法，而无需温和的反应条件需要金属催化剂。
• Synthesis of diarylalkanes through an intramolecular/intermolecular addition sequence by auto-tandem catalysis with strong Brønsted base
  作者：Azusa Kondoh、Chaoyan Ma、Masahiro Terada

  DOI：10.1039/d0cc04512h

  日期：——

  catalysis with a strong Brønsted base enabled the synthesis of diarylalkanes containing a benzofuran moiety. Potassium tert-butoxide efficiently catalyzed both the intramolecular cyclization of less acidic ortho-alkynylaryl benzyl ethers and the following intermolecular addition of diarylmethanes to styrenes, demonstrating the high potential of the catalysis in organic synthesis.

  具有强布朗斯台德碱的自动串联催化能够合成含有苯并呋喃部分的二芳基烷烃。钾叔丁醇催化效率两者的分子内环化较少酸性邻-alkynylaryl苄基醚和以下的分子间加成二芳到苯乙烯，表明在有机合成中催化的高电位。
• p-Toluenesulfonic acid-mediated cyclization of o-(1-alkynyl)anisoles or thioanisoles: synthesis of 2-arylsubstituted benzofurans and benzothiophenes
  作者：Maud Jacubert、Abdallah Hamze、Olivier Provot、Jean-François Peyrat、Jean-Daniel Brion、Mouad Alami

  DOI：10.1016/j.tetlet.2009.03.087

  日期：2009.7

  A variety of 2-arylbenzo[b]furans are readily prepared in good to excellent yields from the cyclization of o-(1-alkynyl)anisole derivatives under mild reaction conditions using an alcoholic media, p-toluenesulfonic acid under microwave irradiation. Starting from the corresponding o-(1-alkynyl)thioanisole derivatives, this friendly and environmentally free-metal procedure has been successfully extended to the synthesis of benzo[b]thiophenes. Relative to the electronic nature of the substituents, the selectivity of the cyclization reaction from differently o,o'-substituted diarylalkynes is also discussed. (C) 2009 Published by Elsevier Ltd.