2-methylene-4,4-diphenyltetrahydrofuran | 1198229-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methylene-4,4-diphenyltetrahydrofuran
• CAS: 1198229-57-0
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: TTZFLBRDLXNUGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-甲基吲哚 、 2-methylene-4,4-diphenyltetrahydrofuran 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 以91%的产率得到1-Methyl-3-(2-methyl-4,4-diphenyloxolan-2-yl)indole
  参考文献：
  名称：

  Thorpe–Ingold effect in copper(II)-catalyzed formal hydroalkoxylation–hydroarylation reaction of alkynols with indoles

  摘要：

  The use of Cu(OTf)(2) as a catalyst for tandem hydroalkoxylation-hydroarylation reaction of alkynes tethered with hydroxyl group is reported. The reaction proceeds at 60 degrees C or even at room temperature with 5 mol% catalyst loading and produces C-3-substituted indoles in good to high yields. The method was shown to be applicable to a broad range of indoles, containing electron-withdrawing and electron-donating substituents, and alkynol substrates bearing sterically demanding substituents in the tether. Interestingly, it was found that Thorpe-Ingold effect is operating for this cyclization reaction. Easy availability and low cost of Cu(OTf)(2) make this method attractive and amenable for large-scale synthesis compared to known literature methods. (C) 2009 Published by Elsevier Ltd

  DOI：

  10.1016/j.tetlet.2009.09.057
• 作为产物：
  描述：

  2,2-diphenylpent-4-yn-1-ol 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 2-methylene-4,4-diphenyltetrahydrofuran
  参考文献：
  名称：

  Thorpe–Ingold effect in copper(II)-catalyzed formal hydroalkoxylation–hydroarylation reaction of alkynols with indoles

  摘要：

  The use of Cu(OTf)(2) as a catalyst for tandem hydroalkoxylation-hydroarylation reaction of alkynes tethered with hydroxyl group is reported. The reaction proceeds at 60 degrees C or even at room temperature with 5 mol% catalyst loading and produces C-3-substituted indoles in good to high yields. The method was shown to be applicable to a broad range of indoles, containing electron-withdrawing and electron-donating substituents, and alkynol substrates bearing sterically demanding substituents in the tether. Interestingly, it was found that Thorpe-Ingold effect is operating for this cyclization reaction. Easy availability and low cost of Cu(OTf)(2) make this method attractive and amenable for large-scale synthesis compared to known literature methods. (C) 2009 Published by Elsevier Ltd

  DOI：

  10.1016/j.tetlet.2009.09.057

文献信息

• Facile Stereoselective Approach to Diverse Spiroheterocyclic Tetrahydropyrans: Concise Synthesis of (+)‐Broussonetine G and H
  作者：Li Zhou、Shu‐Yang Yu、Yong Tang、Lijia Wang

  DOI：10.1002/anie.201907353

  日期：2019.10.14

  exocyclic enol ethers/enamines with methylene malonate and aldehydes has been developed to furnish spiroheterocyclic tetrahydropyrans in high yields with greater than 95:5 d.r. This method is practical, in that 36 examples, including a range of aldehydes and exo-vinyl heterocycles, are presented. By applying the newly developed method, the total synthesis of (+)-broussonetine G and formal synthesis of (+)-broussonetine H

  已开发出高度非对映选择性的铜催化外环烯醇醚/烯胺与丙二酸亚甲基酯和醛的多组分环化反应，可高产率地提供螺杂环四氢吡喃并以95：5 dr以上的产率提供该方法。在36个实例中，包括在提出了醛和外乙烯基杂环。通过应用新开发的方法，可以简明地实现（+）-布罗西汀G的全合成和（+）-布罗西汀H的形式合成。