oxonane-2,7-dione | 112723-42-9

• 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: oxonane-2,7-dione
• CAS: 112723-42-9
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: HWOUBTRJPDBHES-UHFFFAOYSA-N

物化性质

• 沸点：
  332.6±35.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-羟乙基)环己酮 在 玫红酸 、 水 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以39%的产率得到oxonane-2,7-dione
  参考文献：
  名称：

  可见光驱动、铜催化的环烷酮需氧氧化裂解

  摘要：

  已经提出了一种可见光驱动的、铜催化的环烷酮有氧氧化裂解。具有不同环大小和各种α-取代基的各种环烷酮反应良好，以中等至良好的产率得到远端酮酸或二羧酸。

  DOI：

  10.1021/acs.joc.1c00708

文献信息

• Visible Light-Driven, Copper-Catalyzed Aerobic Oxidative Cleavage of Cycloalkanones
  作者：Hong Xin、Xin-Hua Duan、Mingyu Yang、Yiwen Zhang、Li-Na Guo

  DOI：10.1021/acs.joc.1c00708

  日期：2021.6.18

  A visible light-driven, copper-catalyzed aerobic oxidative cleavage of cycloalkanones has been presented. A variety of cycloalkanones with varying ring sizes and various α-substituents reacted well to give the distal keto acids or dicarboxylic acids with moderate to good yields.

  已经提出了一种可见光驱动的、铜催化的环烷酮有氧氧化裂解。具有不同环大小和各种α-取代基的各种环烷酮反应良好，以中等至良好的产率得到远端酮酸或二羧酸。
• Heterogeneous permanganate oxidations: Synthesis of medium ring keto-lactones via substituent directed oxidative cyclisation
  作者：Jagattaran Das、Srinivasan Chandrasekaran

  DOI：10.1016/s0040-4020(01)85664-7

  日期：1994.1

  Homoallyl alcohols 4a-b and 5a-b undergo smooth oxidative cyclisation to give the corresponding ring enlarged keto-lactones under heterogeneous permanganate oxidation conditions.

  均烯丙基醇4a-b和5a-b进行平滑的氧化环化，在高锰酸钾的非均相氧化条件下得到相应的环扩大的酮内酯。
• Pyridinium Chlorochromate in Organic Synthesis. A Facile and Selective Oxidative Cleavage of Enol Ethers
  作者：S. Baskaran、I. Islam、Malini Raghavan、S. Chandrasekaran

  DOI：10.1246/cl.1987.1175

  日期：1987.6.5

  Pyridinium chlorochromate (PCC) has been found to be selective reagent for the oxidative cleavage of enol ethers to esters or keto lactones in high yields.

  研究发现，氯铬酸吡啶鎓（PCC）是一种选择性试剂，可将烯醇醚氧化裂解为酯或酮内酯，并获得高产率。
• Direct Lactonization of Alkenols via Osmium Tetroxide-Mediated Oxidative Cleavage
  作者：Jennifer M. Schomaker、Benjamin R. Travis、Babak Borhan

  DOI：10.1021/ol035057f

  日期：2003.8.1

  A highly efficient, mild, and simple protocol is presented for the tandem OsO4-mediated oxidative cleavage/oxidative lactonization of alkenols to lactones. The protocol couples the OsO4-catalyzed oxidative cleavage of olefins with Oxone as the co-oxidant with the direct oxidation of aldehydes in alcoholic solvents to their corresponding esters.
• Bicyclic β-Hydroxytetrahydrofurans as Precursors of Medium Ring Keto-Lactones
  作者：Helena M. C. Ferraz、Luiz S. Longo

  DOI：10.1021/jo0626109

  日期：2007.4.1

  The reaction of a series of cis-fused bicyclic beta-hydroxytetrahydrofurans with ruthenium tetraoxide, generated in situ from ruthenium trichloride and sodium periodate, afforded 9- and 10-membered keto-lactones in moderate to good yields, in a clean and straightforward fashion. The starting beta-hydroxyethers were obtained from the corresponding 3-alkenols by two alternative procedures, depending on their pattern of substitution: (a) epoxidation by dimethyldioxirane, followed by base-catalyzed cyclization of the resulting epoxyalcohol, and (b) thallium trinitrate-mediated cyclization of the 3-alkenols, a method already described by our group.