1,2-bis(2-(methoxymethoxy)phenyl)ethyne | 1449697-10-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-bis(2-(methoxymethoxy)phenyl)ethyne
• CAS: 1449697-10-2
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: XYILDHLXWCYDBS-UHFFFAOYSA-N

物化性质

• 沸点：
  448.5±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,2-bis(2-(methoxymethoxy)phenyl)ethyne 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以73%的产率得到2,2′-(ethyne-1,2-diyl)diphenol
  参考文献：
  名称：

  Exploring the Potential of Diarylacetylenediols as Hydrogen Bonding Catalysts

  摘要：

  In the course of a search for new classes of hydrogen bonding catalysts, we have examined diarylacetylenediols as potential catalysts for the Diels-Alder reaction. General and efficient methods have been developed for the preparation of these diols. Their structures were systematically modified, and increased activity was observed for those possessing an electron-withdrawing group on the aryl groups. The electron-deficient diarylacetylenediol catalysts, while more active, undergo spontaneous cyclization to the corresponding benzo[b]furans. A mechanism is postulated to explain this facile transformation. Computational studies performed on 2-ethynylphenol help to explain the effect of the alkyne on the conformation and hydrogen bond donating ability of the adjacent OH group. Finally, the crystal structure of one of the diols is reported, and it displays an intricate network of intermolecular hydrogen bonds.

  DOI：

  10.1021/jo400926n
• 作为产物：
  描述：

  1-碘-2-(甲氧基甲氧基)苯 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 27.75h， 生成 1,2-bis(2-(methoxymethoxy)phenyl)ethyne
  参考文献：
  名称：

  Exploring the Potential of Diarylacetylenediols as Hydrogen Bonding Catalysts

  摘要：

  In the course of a search for new classes of hydrogen bonding catalysts, we have examined diarylacetylenediols as potential catalysts for the Diels-Alder reaction. General and efficient methods have been developed for the preparation of these diols. Their structures were systematically modified, and increased activity was observed for those possessing an electron-withdrawing group on the aryl groups. The electron-deficient diarylacetylenediol catalysts, while more active, undergo spontaneous cyclization to the corresponding benzo[b]furans. A mechanism is postulated to explain this facile transformation. Computational studies performed on 2-ethynylphenol help to explain the effect of the alkyne on the conformation and hydrogen bond donating ability of the adjacent OH group. Finally, the crystal structure of one of the diols is reported, and it displays an intricate network of intermolecular hydrogen bonds.

  DOI：

  10.1021/jo400926n

文献信息

• Snap deconvolution: An informatics approach to high-throughput discovery of catalytic reactions
  作者：Konstantin Troshin、John F. Hartwig

  DOI：10.1126/science.aan1568

  日期：2017.7.14

  A triple search for coupling reactions Coupling reactions are, in principle, good candidates for high-throughput discovery: Simply mix a diverse set of reagents and then look for products that combine two or three of their masses. In practice, however, numerous different products might have masses that are too similar to distinguish quickly. Troshin and Hartwig circumvented this problem by screening

  偶联反应的三重搜索原则上，偶联反应是高通量发现的良好候选者：只需混合一组不同的试剂，然后寻找结合了两种或三种质量的产物。然而，在实践中，许多不同的产品可能具有太相似的质量而无法快速区分。Troshin 和 Hartwig 通过并行筛选具有相同反应功能但质量因精心选择的增量而不同的三个试剂池来规避这个问题。然后可以通过三个池中独特的预期质量差异在嘈杂的分布中识别特定产品。科学，这个问题 p。175 平行筛选三个质量不同的相似试剂池有助于快速发现偶联反应。我们提出了一种多维高通量发现催化偶联反应的方法，该方法将分子设计与质谱数据的自动分析和解释相结合。我们同时评估了三个共享相同官能团（卤化物、硼酸、烯烃和炔烃等）但带有非活性取代基的化合物池的反应性，这些取代基具有专门设计的质量差异。选择取代基使得来自多个反应组中任何类型反应的产物在质量上具有独特的差异，从而允许同时鉴定一组反应物中所有转化的产