(-)-(1'S,4'R,7'R,8'R,8a'S)-2-(7',8'-epoxy-8a'-hydroxy-7'-methylperhydro-1'-naphthyl)ethan-8a'-olide | 176980-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (-)-(1'S,4'R,7'R,8'R,8a'S)-2-(7',8'-epoxy-8a'-hydroxy-7'-methylperhydro-1'-naphthyl)ethan-8a'-olide
• 英文别名: (1R,5S,9R,12R,14R)-12-methyl-2,13-dioxatetracyclo[7.5.0.01,5.012,14]tetradecan-3-one
• CAS: 176980-48-6
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: TUPVVPFDUXONCJ-NJIBTWPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(1'S,4'R,7'R,8'R,8a'S)-2-(7',8'-epoxy-8a'-hydroxy-7'-methylperhydro-1'-naphthyl)ethan-8a'-olide 在 正丁基锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 二异丙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 14.0h， 生成 (-)-C10-desmethyl arteannuin B
  参考文献：
  名称：

  Asymmetric Reductive Cyclization. Total Synthesis of (−)-C₁₀-Desmethyl Arteannuin B

  摘要：

  An efficient total synthesis of (-)-C-10-desmethyl arteannuin B (5) has been achieved. The sequence features the use of a chiral auxiliary to introduce absolute asymmetry at an early stage and a stereoselective, chelation-controlled reductive cyclization of 8, using samarium diiodide as the reducing agent. The methodology promises to be applicable to the synthesis of a wide range of analogs capable of being converted to potent antimalarial agents related to artemisinin (1).

  DOI：

  10.1021/jo9600417
• 作为产物：
  描述：

  3-甲基-2-环己烯-1-酮 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以0.22 g的产率得到(-)-(1'S,4'R,7'R,8'R,8a'S)-2-(7',8'-epoxy-8a'-hydroxy-7'-methylperhydro-1'-naphthyl)ethan-8a'-olide
  参考文献：
  名称：

  Asymmetric Reductive Cyclization. Total Synthesis of (−)-C₁₀-Desmethyl Arteannuin B

  摘要：

  An efficient total synthesis of (-)-C-10-desmethyl arteannuin B (5) has been achieved. The sequence features the use of a chiral auxiliary to introduce absolute asymmetry at an early stage and a stereoselective, chelation-controlled reductive cyclization of 8, using samarium diiodide as the reducing agent. The methodology promises to be applicable to the synthesis of a wide range of analogs capable of being converted to potent antimalarial agents related to artemisinin (1).

  DOI：

  10.1021/jo9600417