10-Oxa-tricyclo[6.3.1.0^1,8]dodecan-9-one | 191669-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 10-Oxa-tricyclo[6.3.1.0^1,8]dodecan-9-one
• 英文别名: 10-oxatricyclo[6.3.1.01,8]dodecan-9-one
• CAS: 191669-73-5
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: ZNJFHZYHXUCVRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-Oxa-tricyclo[6.3.1.0^1,8]dodecan-9-one 在 氨 、 lithium 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 9-hydroxy-1-methyl-10-oxabicyclo[6.3.0]undecane
  参考文献：
  名称：

  Cyclopropanation/Reduction of a 3,4-Disubstituted 2(5H)-Furanone:  A Model for C-8 Methylation at the Taxane BC Ring Juncture

  摘要：

  A cyclopropanation/reduction strategy is described that should prove useful for incorporation of the C-8 methyl group at the taxane BC ring juncture. Treatment of model 2(5H)-furanone 6 with various organocopper-based reagents resulted in gamma-deprotonation to the furan oxide rather than the desired conjugate addition. This pathway was established by deuteration studies. Reaction of 6 with dimethylsulfoxonium methylide in DMSO at room temperature also led exclusively to gamma-deprotonation; however, the use of excess methylide at 50 degrees C led to the clean formation of the desired cyclopropanated adduct 13. While the cyclopropane ring in 13 proved resistant to various heterogeneous hydrogenation conditions, treatment with Li/liq NH3 under careful;temperature control(-78 degrees C to -63 degrees C) led to the regioselective formation of the desired ring-opened product 7 with high (16:1) diastereoselectivity.

  DOI：

  10.1021/jo970564u
• 作为产物：
  描述：

  2-Hydroxymethyl-cyclooctan-1-carbonsaeure-lacton 、 dimethylsulfoxonium methylide 以 二甲基亚砜 为溶剂， 反应 21.0h， 以81%的产率得到10-Oxa-tricyclo[6.3.1.0^1,8]dodecan-9-one
  参考文献：
  名称：

  Cyclopropanation/Reduction of a 3,4-Disubstituted 2(5H)-Furanone:  A Model for C-8 Methylation at the Taxane BC Ring Juncture

  摘要：

  A cyclopropanation/reduction strategy is described that should prove useful for incorporation of the C-8 methyl group at the taxane BC ring juncture. Treatment of model 2(5H)-furanone 6 with various organocopper-based reagents resulted in gamma-deprotonation to the furan oxide rather than the desired conjugate addition. This pathway was established by deuteration studies. Reaction of 6 with dimethylsulfoxonium methylide in DMSO at room temperature also led exclusively to gamma-deprotonation; however, the use of excess methylide at 50 degrees C led to the clean formation of the desired cyclopropanated adduct 13. While the cyclopropane ring in 13 proved resistant to various heterogeneous hydrogenation conditions, treatment with Li/liq NH3 under careful;temperature control(-78 degrees C to -63 degrees C) led to the regioselective formation of the desired ring-opened product 7 with high (16:1) diastereoselectivity.

  DOI：

  10.1021/jo970564u