(3S,3aS,6R)-3-Methyl-2,3,4,5,6,7-hexahydro-3a,6-methano-azulen-8-one | 361433-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,3aS,6R)-3-Methyl-2,3,4,5,6,7-hexahydro-3a,6-methano-azulen-8-one
• 英文别名: (1S,2S,8R)-2-methyltricyclo[6.2.1.01,5]undec-4-en-6-one
• CAS: 361433-98-9
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: UQKDLYLALMWDSW-AUTRQRHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S,3aS,6R)-3-Methyl-2,3,4,5,6,7-hexahydro-3a,6-methano-azulen-8-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以66%的产率得到(3S,3aS,6R,8aR)-3-Methyl-octahydro-3a,6-methano-azulen-8-one
  参考文献：
  名称：

  An Asymmetric Approach to Spirocylic Systems:  A Formal Synthesis of Zizaene

  摘要：

  A general route to enantiopure spirocarbocycles is described. The use of various chiral bicyclic lactams 1 that have been doubly alkylated with olefinic halides gives good yields of alpha,alpha -disubstituted chiral lactams 2 which were cyclized to spiro-olefins using ring closure metathesis methodology (Grubbs' catalyst). These spirolactams 3, formed in generally excellent yields, were shown to be smoothly transformed into spirocyclopentenone 6, spirocyclohexenone, 7, and spirolactams 8. Further demonstration of this spirocyclization methodology was featured in a formal synthesis of zizaene, by preparing in enantiomeric form the Coates' intermediate 21. This synthetic effort provided additional examples of the synthetic versatility of chiral bicyclic lactams 2a,b.

  DOI：

  10.1021/jo010439p
• 作为产物：
  描述：

  ((2R,5R,6S)-6-Methyl-8-oxo-spiro[4.4]non-2-yl)-acetaldehyde 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 偶氮二异丁腈 、 Celite 、 三正丁基氢锡 、 二异丁基氢化铝 、 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 92.5h， 生成 (3S,3aS,6R)-3-Methyl-2,3,4,5,6,7-hexahydro-3a,6-methano-azulen-8-one
  参考文献：
  名称：

  An Asymmetric Approach to Spirocylic Systems:  A Formal Synthesis of Zizaene

  摘要：

  A general route to enantiopure spirocarbocycles is described. The use of various chiral bicyclic lactams 1 that have been doubly alkylated with olefinic halides gives good yields of alpha,alpha -disubstituted chiral lactams 2 which were cyclized to spiro-olefins using ring closure metathesis methodology (Grubbs' catalyst). These spirolactams 3, formed in generally excellent yields, were shown to be smoothly transformed into spirocyclopentenone 6, spirocyclohexenone, 7, and spirolactams 8. Further demonstration of this spirocyclization methodology was featured in a formal synthesis of zizaene, by preparing in enantiomeric form the Coates' intermediate 21. This synthetic effort provided additional examples of the synthetic versatility of chiral bicyclic lactams 2a,b.

  DOI：

  10.1021/jo010439p

文献信息

• An Asymmetric Approach to Spirocylic Systems:  A Formal Synthesis of Zizaene
  作者：Robert C. Hughes、Curt A. Dvorak、A. I. Meyers

  DOI：10.1021/jo010439p

  日期：2001.8.1

  A general route to enantiopure spirocarbocycles is described. The use of various chiral bicyclic lactams 1 that have been doubly alkylated with olefinic halides gives good yields of alpha,alpha -disubstituted chiral lactams 2 which were cyclized to spiro-olefins using ring closure metathesis methodology (Grubbs' catalyst). These spirolactams 3, formed in generally excellent yields, were shown to be smoothly transformed into spirocyclopentenone 6, spirocyclohexenone, 7, and spirolactams 8. Further demonstration of this spirocyclization methodology was featured in a formal synthesis of zizaene, by preparing in enantiomeric form the Coates' intermediate 21. This synthetic effort provided additional examples of the synthetic versatility of chiral bicyclic lactams 2a,b.