1-phenyl-2-(2-(2-phenylethynyl)phenoxy)propan-1-one | 1192115-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-2-(2-(2-phenylethynyl)phenoxy)propan-1-one
• 英文别名: 2-(2-(2-phenylethynyl)phenoxy)-1-phenylpropan-1-one；1-phenyl-2-(2-phenylethynylphenoxy)propan-1-one；1-Phenyl-2-[2-(2-phenylethynyl)phenoxy]propan-1-one
• CAS: 1192115-38-0
• 化学式: C₂₃H₁₈O₂
• 分子量: 326.395
• InChiKey: SLKYBSHTWDEHEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(2-(2-phenylethynyl)phenoxy)propan-1-one 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以86%的产率得到3-benzyl-2-methylbenzofuran
  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
• 作为产物：
  描述：

  2-溴苯丙酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 二异丙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.0h， 生成 1-phenyl-2-(2-(2-phenylethynyl)phenoxy)propan-1-one
  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

• Phase-Transfer-Catalyzed Intramolecular Cyclization of<i>ortho</i>-Alkynyl Phenyl Ether Derivatives for Synthesis of 2,3-Disubstituted Benzo[<i>b</i>]furans
  作者：Jie Hu、Lu-Yong Wu、Xiang-Chuan Wang、Yuan-Yuan Hu、Yan-Ning Niu、Xue-Yuan Liu、Shangdong Yang、Yong-Min Liang

  DOI：10.1002/adsc.200900649

  日期：2010.2.15

  A variety of substituted benzo[b]furans are readily prepared in good to excellent yields under the mild reaction conditions from o-(1-alkynylphenoxy)-1-phenylethanone under phase-transfer catalysis (PTC). This methodology accommodates simple experimental operations, inexpensive and environmentally benign catalysts, metal catalyst-free conditions, facile reagents and the possibility to conduct large-scale

  在相转移催化（PTC）下，由邻-（1-炔基苯氧基）-1-苯基乙酮在温和的反应条件下，可以容易地以良好的产率或优异的产率制备各种取代的苯并[ b ]呋喃。该方法学适用于简单的实验操作，廉价且对环境无害的催化剂，无金属催化剂的条件，简便的试剂以及进行大规模制备的可能性。通过整体结构异构化发展碳-碳键形成过程代表了最经济的方法。
• Iron-catalyzed annulations of 2-(2-alkynyl)phenoxy)-1-arylethanones leading to substituted naphthalen-1-ols
  作者：Zhi-Qiang Wang、Yun Liang、Yong Lei、Ming-Bo Zhou、Jin-Heng Li

  DOI：10.1039/b911669a

  日期：——

  A novel intramolecular annulation of 1-(2-alkynylphenoxy)propan-2-ones catalyzed by iron, an economical and environmentally-benign transition metal, has been developed; this new atom-economical route includes dual C–H functionalizations to construct the naphthalen-1-ol or anthracen-1-ol skeletons.

  在铁这种既经济又对环境无害的过渡金属的催化下，开发出了一种新型的 1-(2-炔基苯酚氧基)丙-2-酮分子内环化反应；这种新的原子经济路线包括双 C-H 功能化，以构建萘-1-醇或蒽-1-醇骨架。
• Iron-Mediated [3 + 2] or [3 + 3] Annulation of 2-(2-(Ethynyl)phenoxy)-1-arylethanones: Selective Synthesis of Indeno[1,2-<i>c</i>]chromenes and 5<i>H</i>-Naphtho[1,2-<i>c</i>]chromenes
  作者：Zhi-Qiang Wang、Yong Lei、Ming-Bo Zhou、Guo-Xiang Chen、Ren-Jie Song、Ye-Xiang Xie、Jin-Heng Li

  DOI：10.1021/ol102761m

  日期：2011.1.7

  An iron-mediated tandem annulation strategy has been developed for the synthesis of numerous functional indeno[1,2-c]chromenes and 5H-naphtho[1,2-c]chromenes. This work is the first to disclose an iron-mediated method through sequential electrophilic addition of a ketone to an alkyne and annulation tandem reaction. Importantly, a halide is introduced into the products by a ring-opening process among the annulation of alkynylcyclopropanes, which makes the methodology more attractive for organic synthesis.