2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-di(benzoylbiphenylethynyl)benzoate | 791090-30-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-di(benzoylbiphenylethynyl)benzoate
• 英文别名: 2-[2-(2-Methoxyethoxy)ethoxy]ethyl 3,5-bis[2-[4-(4-benzoylphenyl)phenyl]ethynyl]benzoate；2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-bis[2-[4-(4-benzoylphenyl)phenyl]ethynyl]benzoate
• CAS: 791090-30-7
• 化学式: C₅₆H₄₄O₇
• 分子量: 828.961
• InChiKey: ZGFGASWMVNHESE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-di(benzoylbiphenylethynyl)benzoate 在 对硝基苯酚 、 molybdenum triamide 作用下， 以 四氯化碳 为溶剂， 反应 22.0h， 以77%的产率得到
  参考文献：
  名称：

  Arylene Ethynylene Macrocycles Prepared by Precipitation-Driven Alkyne Metathesis

  摘要：

  A convenient, multigram-scale synthesis of arylene ethynylene macrocycles near room temperature is described. Driven by the precipitation of a diarylacetylene byproduct, alkyne metathesis produces the desired macrocycles in one step from monomers in high yields.

  DOI：

  10.1021/ja046531v
• 作为产物：
  描述：

  三甘醇单甲醚 在 三乙胺 copper(l) iodide 、 tris(dibenzylideneacetone)dipalladium (0) 、 四丁基氟化铵 、 溶剂黄146 、 三苯基膦 、 diphenylammonium triflate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.08h， 生成 2-[2-(2-methoxyethoxy)ethoxy]ethyl 3,5-di(benzoylbiphenylethynyl)benzoate
  参考文献：
  名称：

  Arylene Ethynylene Macrocycles Prepared by Precipitation-Driven Alkyne Metathesis

  摘要：

  A convenient, multigram-scale synthesis of arylene ethynylene macrocycles near room temperature is described. Driven by the precipitation of a diarylacetylene byproduct, alkyne metathesis produces the desired macrocycles in one step from monomers in high yields.

  DOI：

  10.1021/ja046531v

文献信息

• Reaction Pathways Leading to Arylene Ethynylene Macrocycles via Alkyne Metathesis
  作者：Wei Zhang、Jeffrey S. Moore

  DOI：10.1021/ja053466w

  日期：2005.8.24

  Mechanistic studies on the direct formation of arylene ethynylene macrocycles via alkyne metathesis catalyzed by a molybdenum complex are reported. Gel permeation chromatography (GPC) and matrix-assisted laser desorption ionization (MALDI) mass spectrometry on the products from metathesis of monomer 1 show the initial formation of linear oligomers and large macrocycles (n > 6), followed by their transformation into the thermodynamically most stable product distribution-mainly the cyclic hexamer. Variable temperature and scrambling experiments reveal the reversibility of macrocycle formation. Nearly identical product distributions are observed from the cross metathesis of hexacycle 2 with diphenylacetylene and from the metathesis of bis(phenylethynyl) substituted monomer 4, demonstrating that macrocycle formation is thermodynamically rather than kinetically controlled. The metathesis byproduct, 3-hexyne, is shown to inhibit the catalyst. It is suggested that the relative metathesis rates of dialkylalkynes versus diarylalkynes trap the catalyst in a nonproductive manifold, rendering it unavailable for the productive metathesis of aryl alkylalkyne substrates. This finding indicates that dialkyl-substituted alkyne byproducts should be avoided (or efficiently removed) if the metatheses of aryl substrates, especially those with electron-withdrawing groups, are to proceed to high conversion.
• Arylene Ethynylene Macrocycles Prepared by Precipitation-Driven Alkyne Metathesis
  作者：Wei Zhang、Jeffrey S. Moore

  DOI：10.1021/ja046531v

  日期：2004.10.1

  A convenient, multigram-scale synthesis of arylene ethynylene macrocycles near room temperature is described. Driven by the precipitation of a diarylacetylene byproduct, alkyne metathesis produces the desired macrocycles in one step from monomers in high yields.