5,6-diethyl-1,3-dihydroisobenzofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 5,6-diethyl-1,3-dihydroisobenzofuran
• 英文别名: 5,6-Diethyl-1,3-dihydro-2-benzofuran
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: OTHLCVDZUFKPBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-己炔 、 丙炔醚 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 丙酮 为溶剂， 以19%的产率得到5,6-diethyl-1,3-dihydroisobenzofuran
  参考文献：
  名称：

  Ruthenium Carbene Mediated [2+2+2] Cyclotrimerizations

  摘要：

  第二代格拉布斯催化剂和霍韦达-格拉布斯催化剂既能催化二炔与炔烃的交叉[2+2+2]环三聚反应，也能催化二炔的二聚或三聚反应。通过选择反应条件，我们可以选择一种特定的工艺。该过程对不对称二炔具有选择性。

  DOI：

  10.1055/s-0030-1258521

文献信息

• Iridium Complex-Catalyzed [2+2+2] Cycloaddition of α,ω-Diynes with Monoynes and Monoenes
  作者：Satoko Kezuka、Shigeru Tanaka、Toshihito Ohe、Yoshihiko Nakaya、Ryo Takeuchi

  DOI：10.1021/jo051874c

  日期：2006.1.1

  [Ir(cod)Cl](2)/DPPE was found to be a new catalyst for the cycloaddition of alpha,omega-diynes with monoynes to give polysubstituted benzene derivatives in high yields. Internal monoynes as well as terminal monoynes could be used. The reaction tolerates a broad range of functional groups such as alcohol, amine, alkene, ether, halogen, and nitrile. The reaction of 1,6-octadiyne derivatives with 1-alkynes gives ortho products and meta products. The regioselectivity could be controlled by the choice of ligand. The reaction with DPPE was meta selective, with meta selectivity of up to 82%. The reaction with DPPF was ortho selective, with ortho selectivity of up to 88%. We propose a mechanism to account for this regioselective cycloaddition. [Ir(cod)Cl-2]2/DPPE also catalyzed the cycloaddition of alpha-omega-diynes with 2,5-dihydrofuran to give bicyclic cyclohexadiene derivatives. The reaction with 2,3-dihydrofuran and n-butyl vinyl ether gave benzene derivatives instead of cyclohexadiene derivatives. We also propose a mechanism to account for this novel aromatization that includes cleavage of the C-O bond.
• Ruthenium Carbene Mediated [2+2+2] Cyclotrimerizations
  作者：Javier Pérez-Castells、Álvaro Mallagaray、Sandra Medina、Gema Domínguez

  DOI：10.1055/s-0030-1258521

  日期：2010.9

  Second-generation Grubbs’ catalyst and Hoveyda-Grubbs’ catalyst are able to catalyze both crossed [2+2+2] cyclotrimerization of diynes with alkynes and di- or trimerizations of diynes. Selection of the reaction conditions allows us to favor one particular process. The process is selective when applied to unsymmetric diynes.

  第二代格拉布斯催化剂和霍韦达-格拉布斯催化剂既能催化二炔与炔烃的交叉[2+2+2]环三聚反应，也能催化二炔的二聚或三聚反应。通过选择反应条件，我们可以选择一种特定的工艺。该过程对不对称二炔具有选择性。