2-methyl-5-(2-methylhexa-2,5-dien-3-yl)-3-pentyl-4-phenylfuran | 1219966-31-0

• 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-methyl-5-(2-methylhexa-2,5-dien-3-yl)-3-pentyl-4-phenylfuran
• CAS: 1219966-31-0
• 化学式: C₂₃H₃₀O
• 分子量: 322.491
• InChiKey: LLOLQCFRGKAEHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (Z)-2-methyl-6-pentyl-5-phenyl-5-octen-3-yn-2,7-diol 、 3-溴丙烯 在 palladium dichloride 作用下， 以 2,4-滴二甲胺盐 为溶剂， 反应 4.0h， 以694.8 mg的产率得到2-methyl-5-(2-methylhexa-2,5-dien-3-yl)-3-pentyl-4-phenylfuran
  参考文献：
  名称：

  Synthesis of Polysubstituted Furans Based on a Stepwise Sonogashira Coupling of (Z)-3-Iodoalk-2-en-1-ols with Terminal Propargylic Alcohols and Subsequent Au(I)- or Pd(II)-Catalyzed Cyclization−Aromatization via Elimination of H₂O

  摘要：

  Recently, we have developed highly regio- and stereoselective carbometalation of 2-alkynols and 2,3-allenols. The organometallacyclic intermediates may be trapped with 12 to afford 3-iodoalk-2-en-1-ols. These 3-iodoalk-2-en-1-ols may readily undergo the Sonogashira coupling with terminal propargyl alcohols to form 4-alkyn-2-ene-1,6-diols. Subsequent cycloisomerization in DMA or CH2Cl2 with Au(PPh3)Cl and AgOTf as the catalyst would afford polysubstituted 2-(1-alkenyl)furans; with PdCl2 as the catalyst and the reaction in DMA in the presence of allylic bromides, the same substrates afforded polysubstituted 2-( 1,4-alkadienyl)furans. In both types of catalyzed cyclization reactions, the elimination of H2O promoted the aromatization to form the furan ring. Different alkyl or aryl groups could be introduced into different positions of furans due to the substituent-loading capability of 3-iodoalkenols and diversity of the terminal propargyl alcohols and allylic bromides.

  DOI：

  10.1021/jo100146p

文献信息

• Synthesis of Polysubstituted Furans Based on a Stepwise Sonogashira Coupling of (Z)-3-Iodoalk-2-en-1-ols with Terminal Propargylic Alcohols and Subsequent Au(I)- or Pd(II)-Catalyzed Cyclization−Aromatization via Elimination of H₂O
  作者：Xiaobing Zhang、Zhan Lu、Chunling Fu、Shengming Ma

  DOI：10.1021/jo100146p

  日期：2010.4.16

  Recently, we have developed highly regio- and stereoselective carbometalation of 2-alkynols and 2,3-allenols. The organometallacyclic intermediates may be trapped with 12 to afford 3-iodoalk-2-en-1-ols. These 3-iodoalk-2-en-1-ols may readily undergo the Sonogashira coupling with terminal propargyl alcohols to form 4-alkyn-2-ene-1,6-diols. Subsequent cycloisomerization in DMA or CH2Cl2 with Au(PPh3)Cl and AgOTf as the catalyst would afford polysubstituted 2-(1-alkenyl)furans; with PdCl2 as the catalyst and the reaction in DMA in the presence of allylic bromides, the same substrates afforded polysubstituted 2-( 1,4-alkadienyl)furans. In both types of catalyzed cyclization reactions, the elimination of H2O promoted the aromatization to form the furan ring. Different alkyl or aryl groups could be introduced into different positions of furans due to the substituent-loading capability of 3-iodoalkenols and diversity of the terminal propargyl alcohols and allylic bromides.