4-(but-2-yn-1-yloxy)-4-methoxycyclohexa-2,5-dienone | 1448451-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(but-2-yn-1-yloxy)-4-methoxycyclohexa-2,5-dienone
• 英文别名: 4-But-2-ynoxy-4-methoxycyclohexa-2,5-dien-1-one
• CAS: 1448451-03-3
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: BLHWMZXSTLSIPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(but-2-yn-1-yloxy)-4-methoxycyclohexa-2,5-dienone 、 联硼酸频那醇酯 在 copper(l) chloride 、 sodium t-butanolate 、 (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 48.5h， 以88%的产率得到
  参考文献：
  名称：

  Cu-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Enynes

  摘要：

  The first Cu-catalyzed asymmetric borylative cyclization of cyclohexadienone-containing 1,6-enynes is achieved through a tandem process: selective beta-borylation of propargylic ether and subsequent conjugate addition to cyclohexadienone. The reaction proceeds with excellent regioselectivity and enantioselectivity to afford an optically pure cis-hydrobenzofuran framework bearing alkenylboronate and enone substructures. Furthermore, the resulting bicyclic products could be converted to bridged and tricyclic ring structures. This method extends the realm of Cu-catalyzed asymmetric tandem reactions using bis(pinacolato)diboron (B(2)pin(2)).

  DOI：

  10.1021/ja404593c
• 作为产物：
  描述：

  2-丁炔-1-醇 、 4-甲氧基苯酚 在 [双(三氟乙酰氧基)碘]苯 作用下， 以4%的产率得到4-(but-2-yn-1-yloxy)-4-methoxycyclohexa-2,5-dienone
  参考文献：
  名称：

  Cu-Catalyzed Asymmetric Borylative Cyclization of Cyclohexadienone-Containing 1,6-Enynes

  摘要：

  The first Cu-catalyzed asymmetric borylative cyclization of cyclohexadienone-containing 1,6-enynes is achieved through a tandem process: selective beta-borylation of propargylic ether and subsequent conjugate addition to cyclohexadienone. The reaction proceeds with excellent regioselectivity and enantioselectivity to afford an optically pure cis-hydrobenzofuran framework bearing alkenylboronate and enone substructures. Furthermore, the resulting bicyclic products could be converted to bridged and tricyclic ring structures. This method extends the realm of Cu-catalyzed asymmetric tandem reactions using bis(pinacolato)diboron (B(2)pin(2)).

  DOI：

  10.1021/ja404593c