2-iodo-4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one | 681259-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 2-iodo-4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one
• 英文别名: 7-iodo-3a,5,5-trimethyl-4,6,7,7a-tetrahydro-3H-1-benzofuran-2-one
• CAS: 681259-97-2
• 化学式: C₁₁H₁₇IO₂
• 分子量: 308.159
• InChiKey: PYTYWVRTJBSKCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-iodo-4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one 在 Fusarium tricinctum strain 作用下， 以 丙酮 为溶剂， 反应 336.0h， 以47.1%的产率得到cis ( - )-2-hydroxy-4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one
  参考文献：
  名称：

  Biotransformations of bicyclic trimethylcyclohexane chloro-, bromo- and iodolactones using fungal strains

  摘要：

  Several fungal strains (Fusarium, Botrytis, Beauveria) were screened for their ability to transform three bicyclic halo-gamma-lactones with a trimethylcyclohexane ring. Most of the micro-organisms carried out hydrolytic dehalogenation and transformed these lactones into two hydroxy-gamma-lactones: cis (-)-2-hydroxy-4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one and trans (+)-2-hydroxy- 4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one. The structures of all substrates and products were established on the basis of their spectral data and X-ray analysis. The method presented offers an alternative route to obtaining hydroxy-lactones with high enantiomeric excess.

  DOI：

  10.3109/10242422.2010.538688
• 作为产物：
  描述：

  2-(1,4,4-trimethyl-cyclohex-2-enyl) acetic acid 在 碘 、 碳酸氢钠 、 potassium iodide 作用下， 生成 2-iodo-4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one
  参考文献：
  名称：

  Biotransformations of bicyclic trimethylcyclohexane chloro-, bromo- and iodolactones using fungal strains

  摘要：

  Several fungal strains (Fusarium, Botrytis, Beauveria) were screened for their ability to transform three bicyclic halo-gamma-lactones with a trimethylcyclohexane ring. Most of the micro-organisms carried out hydrolytic dehalogenation and transformed these lactones into two hydroxy-gamma-lactones: cis (-)-2-hydroxy-4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one and trans (+)-2-hydroxy- 4,4,6-trimethyl-9-oxabicyclo[4.3.0]nonan-8-one. The structures of all substrates and products were established on the basis of their spectral data and X-ray analysis. The method presented offers an alternative route to obtaining hydroxy-lactones with high enantiomeric excess.

  DOI：

  10.3109/10242422.2010.538688