1-[(3R)-[3-(1-bromo-1-methylethyl)]tetrahydrofuran-2-yl]-2-propanone | 676248-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 1-[(3R)-[3-(1-bromo-1-methylethyl)]tetrahydrofuran-2-yl]-2-propanone
• 英文别名: 1-[(3R)-3-(2-bromopropan-2-yl)oxolan-2-yl]propan-2-one
• CAS: 676248-81-0
• 化学式: C₁₀H₁₇BrO₂
• 分子量: 249.148
• InChiKey: YPHAYRMTIOXJOE-VEDVMXKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-[(1S,3R)-2,2-dimethyl-3-(2-methoxymethyloxyethyl)cyclopropyl]-2-propanone 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 生成 (E)-4-[(3R)-2,2-dimethyltetrahydrofuran-3-yl]-3-buten-2-one 、 1-[(3R)-[3-(1-bromo-1-methylethyl)]tetrahydrofuran-2-yl]-2-propanone 、 (3E,5R)-6-methyl-5-(2-methoxymethyloxyethyl)-3,6-heptadien-2-one 、 (3E,5R)-6-bromo-6-methyl-5-(2-methoxymethyloxyethyl)-3-hepten-2-one
  参考文献：
  名称：

  Functionalization of the Methyl Ketone Fragment in 1-[(1S,3R)-2,2-Dimethyl-3-(2-methoxymethyloxyethyl)cyclopropyl]-2-propanone

  摘要：

  Deprotonation of 1-[(1S,3R)-2,2-dimethyl-3-(2-methoxymethyloxyethyl)cyclopropyl]-2-propanone with lithium diisopropylamide in THF at -78degreesC and subsequent treatment of the resulting enolate with Me3SiCl yielded mainly the corresponding terminal silyl enol ether. The condensation of intermediate enolate with benzaldehyde regioselectively afforded a mixture of the corresponding aldol and its dehydration product. The reactions of the title ketone with NBS, as well as of the silyl enol ethers derived therefrom with I-2, led to formation of mixtures of products via opening of the cyclopropane ring.

  DOI：

  10.1023/b:rujo.0000010207.63528.f6

文献信息

• Functionalization of the Methyl Ketone Fragment in 1-[(1S,3R)-2,2-Dimethyl-3-(2-methoxymethyloxyethyl)cyclopropyl]-2-propanone
  作者：F. A. Gimalova (Akbutina)、I. F. Sadretdinov、L. V. Spirikhin、M. S. Miftakhov

  DOI：10.1023/b:rujo.0000010207.63528.f6

  日期：2003.9

  Deprotonation of 1-[(1S,3R)-2,2-dimethyl-3-(2-methoxymethyloxyethyl)cyclopropyl]-2-propanone with lithium diisopropylamide in THF at -78degreesC and subsequent treatment of the resulting enolate with Me3SiCl yielded mainly the corresponding terminal silyl enol ether. The condensation of intermediate enolate with benzaldehyde regioselectively afforded a mixture of the corresponding aldol and its dehydration product. The reactions of the title ketone with NBS, as well as of the silyl enol ethers derived therefrom with I-2, led to formation of mixtures of products via opening of the cyclopropane ring.