9-oxa-bicyclo[6.1.0]nonan-4-one | 28399-88-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-oxa-bicyclo[6.1.0]nonan-4-one
• 英文别名: (1R,8S)-9-oxabicyclo[6.1.0]nonan-4-one
• CAS: 28399-88-4；34958-38-8
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: IUCLHDTXBOXKPX-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

安全信息

• 海关编码：
  2932999099

反应信息

• 作为产物：
  描述：

  顺-环辛烯 在 甲基(三氟甲基)-1,3-二环氧丙烷 、 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 9-oxa-bicyclo[6.1.0]nonan-4-one
  参考文献：
  名称：

  Concerning the Efficient Conversion of Epoxy Alcohols into Epoxy Ketones Using Dioxiranes

  摘要：

  Representative epoxy alcohols are cleanly converted into the corresponding epoxy ketones in high yield by selective oxidation using dimethyldioxirane (1a) and its trifluoro analogue (1b) under mild conditions. The oxidation is found to take place leaving the configuration at the epoxy functionality unaffected. The direct oxyfunctionalization of simple cyclic epoxides with the powerful dioxirane 1b provides another attractive method to access epoxy ketones regioselectively.

  DOI：

  10.1021/jo048816w

文献信息

• Heterolytic oxygen–oxygen bond formation via gem-dialkylperoxonium ions
  作者：Stephen P. Best、A. J. Bloodworth、Michael D. Spencer

  DOI：10.1039/c39900000416

  日期：——

  for the cis and trans isomers of 4,5-epoxycyclo-octyl hydroperoxide coupled with the formation of oxygen (identified by Raman spectroscopy) and bicyclic ethers suggest a mechanism involving the heterolytic formation of protonated alkyl hydrotrioxides by nucleophilic attack of hydroperoxide on gem-dialkylperoxonium ions.

  4,5-环氧环辛基氢过氧化物的顺式和反式异构体不同程度的分解，以及氧的形成（通过拉曼光谱法鉴定）和双环醚，表明一种机制涉及氢过氧化物的亲核攻击杂化形成质子化氢过氧化物在宝石-二烷基过氧鎓离子上。
• Concerning the Efficient Conversion of Epoxy Alcohols into Epoxy Ketones Using Dioxiranes
  作者：Lucia D'Accolti、Caterina Fusco、Cosimo Annese、Maria R. Rella、Joanna S. Turteltaub、Paul G. Williard、Ruggero Curci

  DOI：10.1021/jo048816w

  日期：2004.11.1

  Representative epoxy alcohols are cleanly converted into the corresponding epoxy ketones in high yield by selective oxidation using dimethyldioxirane (1a) and its trifluoro analogue (1b) under mild conditions. The oxidation is found to take place leaving the configuration at the epoxy functionality unaffected. The direct oxyfunctionalization of simple cyclic epoxides with the powerful dioxirane 1b provides another attractive method to access epoxy ketones regioselectively.