(3-benzylbenzofuran-2-yl)(4-methoxyphenyl)methanone | 1346668-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-benzylbenzofuran-2-yl)(4-methoxyphenyl)methanone
• 英文别名: 3-benzyl-2-(4-methoxybenzoyl)-benzofuran；(3-Benzyl-1-benzofuran-2-yl)-(4-methoxyphenyl)methanone
• CAS: 1346668-00-5
• 化学式: C₂₃H₁₈O₃
• 分子量: 342.394
• InChiKey: BXEJZZCBDWPWJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-碘苯氧基)-1-(4-甲氧基苯基)乙酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium tert-butylate 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (3-benzylbenzofuran-2-yl)(4-methoxyphenyl)methanone
  参考文献：
  名称：

  tert-BuOK-mediated carbanion–yne intramolecular cyclization: synthesis of 2-substituted 3-benzylbenzofurans

  摘要：

  A mild, efficient, and regioselective carbanion-yne intramolecular cyclization mediated by t-BuOK for the synthesis of 2-substituted 3-benzylbenzofurans is developed. It was started from o-iodophenol (1), based on O-alkylation, and the Sonogashira reaction in sequence to produce 2-(2-phenylethynyl-phenoxy)-1-arylalkanones (5). An intramolecular carbanion-yne 5-exo-dig cyclization reaction of 5, which was mediated by t-BuOK, yielded title benzofurans in good yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.144

文献信息

• A highly efficient ultrasound-promoted synthesis of 2,3-disubstituted benzo[b]furans via intramolecular C–C bond formation in ionic liquid[bmim]BF₄at room temperature
  作者：Nisha Yadav、Mohd. Kamil Hussain、Mohd. Imran Ansari、Puneet K. Gupta、Kanchan Hajela

  DOI：10.1039/c2ra22355d

  日期：——

  An efficient ultrasound-promoted synthesis of 2,3-disubstituted benzo[b]furans in the ionic liquid [bmim]BF4 at room temperature is reported. 5-exo-dig carbanion–yne intramolecular cyclization is mediated using anhydrous K3PO4 as a mild, inexpensive base under atmospheric conditions giving the title benzo[b]furans in excellent yields. Ionic liquid [bmim]BF4 has been used both as a reaction medium,

  据报道，在室温下，在离子液体[bmim] BF 4中超声有效地促进了2,3-二取代的苯并[ b ]呋喃的合成。在大气条件下，使用无水K 3 PO 4作为温和且廉价的碱，可以介导5 -exo-dig Carbanion-yne分子内环化反应，从而以优异的收率得到标题为benzo [ b ]呋喃的化合物。离子液体[bmim] BF 4既用作反应介质，又用作形成CC键的催化剂。
• Intermolecular Sonogashira Coupling and Intramolecular 5-<i>Exo</i>-<i>dig</i> Cycloisomerization Cascade: A One-Pot Pathway for Accessing (3-Benzylbenzofuran-2-yl)(phenyl)methanones
  作者：Dakoju Ravi Kishore、Gedu Satyanarayana

  DOI：10.1021/acs.joc.2c01101

  日期：2022.8.5

  straightforward strategy enabling access to 2,3-disubstituted benzo[b]furans. The whole synthetic process proceeds via a domino intermolecular Sonogashira coupling of 2-(2-bromophenoxy)-1-phenylethan-1-ones/alkyl 2-(2-bromophenoxy)acetates/2-(2-bromophenoxy)acetonitrile/1-(2-bromophenoxy)propan-2-one with terminal acetylenes followed by an intramolecular carbanion-yne cyclization in a 5-exo-dig manner and subsequent

  在此，我们提出了一种有效且直接的策略，能够获得 2,3-二取代苯并[ b ]呋喃。整个合成过程通过2-(2-溴苯氧基)-1-苯乙烷-1-酮/烷基 2-(2-溴苯氧基)乙酸酯/2-(2-溴苯氧基)乙腈/1-( 2-溴苯氧基)propan-2-one 与末端乙炔，然后以 5- exo - dig方式进行分子内碳负离子-炔环化，随后进行双键异构化。值得注意的是，已经以一锅法构建了两个 C-C 键，并且以良好的官能团耐受性完成了多种 (3-苄基苯并呋喃-2-基)(苯基)甲酮。
• tert-BuOK-mediated carbanion–yne intramolecular cyclization: synthesis of 2-substituted 3-benzylbenzofurans
  作者：Po-Yuan Chen、Tzu-Pin Wang、Keng-Shiang Huang、Chai-Lin Kao、Jui-Chi Tsai、Eng-Chi Wang

  DOI：10.1016/j.tet.2011.09.144

  日期：2011.12

  A mild, efficient, and regioselective carbanion-yne intramolecular cyclization mediated by t-BuOK for the synthesis of 2-substituted 3-benzylbenzofurans is developed. It was started from o-iodophenol (1), based on O-alkylation, and the Sonogashira reaction in sequence to produce 2-(2-phenylethynyl-phenoxy)-1-arylalkanones (5). An intramolecular carbanion-yne 5-exo-dig cyclization reaction of 5, which was mediated by t-BuOK, yielded title benzofurans in good yields. (C) 2011 Elsevier Ltd. All rights reserved.