(3aS,7aS,Z)-7a-(3-iodopropyl)-3-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethylidene)-2,3,3a,4-tetrahydrobenzofuran-5(7aH)-one | 1448451-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (3aS,7aS,Z)-7a-(3-iodopropyl)-3-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethylidene)-2,3,3a,4-tetrahydrobenzofuran-5(7aH)-one
• CAS: 1448451-39-5
• 化学式: C₁₉H₂₈BIO₄
• 分子量: 458.144
• InChiKey: GUSVTTHBHDKOGB-QQCBQXDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3aS,7aS,Z)-7a-(3-iodopropyl)-3-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethylidene)-2,3,3a,4-tetrahydrobenzofuran-5(7aH)-one 在 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.03h， 以55%的产率得到(3aS,6aR,91S,Z)-3-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethylidene)octahydroindeno[4-b]furan-5(6H)-one
  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：

  (3aS,7aS,Z)-7a-(3-bromopropyl)-3-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethylidene)-2,3,3a,4-tetrahydrobenzofuran-5(7aH)-one 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以95%的产率得到(3aS,7aS,Z)-7a-(3-iodopropyl)-3-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethylidene)-2,3,3a,4-tetrahydrobenzofuran-5(7aH)-one
  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