(3S,3aS,5aS,9bS,E)-8-(methoxyimino)-3,5a,9-trimethyl-3,3a,4,5,5a,6,7,8-octahydronaphtho[1,2-b]furan-2(9bH)-one | 1575700-20-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (3S,3aS,5aS,9bS,E)-8-(methoxyimino)-3,5a,9-trimethyl-3,3a,4,5,5a,6,7,8-octahydronaphtho[1,2-b]furan-2(9bH)-one
• CAS: 1575700-20-7
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: YVZFSSHAORMSIK-REXLKUQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  苯磺酰基叠氮化物 、 (3S,3aS,5aS,9bS,E)-8-(methoxyimino)-3,5a,9-trimethyl-3,3a,4,5,5a,6,7,8-octahydronaphtho[1,2-b]furan-2(9bH)-one 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 silver(I) acetate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以79%的产率得到N-[{(3S,3aS,5aS,9bS,E)-8-(methoxyimino)-3,5a-dimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydronaphtho[1,2-b]furan-9-yl}methyl]benzenesulfonamide
  参考文献：
  名称：

  Iridium-Catalyzed Intermolecular Amidation of sp³ C–H Bonds: Late-Stage Functionalization of an Unactivated Methyl Group

  摘要：

  Reported herein is the iridium-catalyzed direct amidation of unactivated sp(3) C-H bonds. With sulfonyl and acyl azides as the amino source, the amidation occurs efficiently under mild conditions over a wide range of unactivated methyl groups with high functional group tolerance. This procedure can be successfully applied for the direct introduction of an amino group into complex compounds and thus can serve as a powerful synthetic tool for late-stage C-H functionalization.

  DOI：

  10.1021/ja501014b
• 作为产物：
  描述：

  山道年 在 吡啶 、 Wilkinson's catalyst 、 氢气 作用下， 以 乙酸乙酯 、 苯酚 为溶剂， 反应 12.0h， 生成 (3S,3aS,5aS,9bS,E)-8-(methoxyimino)-3,5a,9-trimethyl-3,3a,4,5,5a,6,7,8-octahydronaphtho[1,2-b]furan-2(9bH)-one
  参考文献：
  名称：

  Iridium-Catalyzed Intermolecular Amidation of sp³ C–H Bonds: Late-Stage Functionalization of an Unactivated Methyl Group

  摘要：

  Reported herein is the iridium-catalyzed direct amidation of unactivated sp(3) C-H bonds. With sulfonyl and acyl azides as the amino source, the amidation occurs efficiently under mild conditions over a wide range of unactivated methyl groups with high functional group tolerance. This procedure can be successfully applied for the direct introduction of an amino group into complex compounds and thus can serve as a powerful synthetic tool for late-stage C-H functionalization.

  DOI：

  10.1021/ja501014b