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

• 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。
• Photocatalytic Aerobic Oxidative Ring Expansion of Cyclic Ketones to Macrolactones by Cerium and Cyanoanthracene Catalysis
  作者：Jianbo Du、Xiaokun Yang、Xin Wang、Qing An、Xu He、Hui Pan、Zhiwei Zuo

  DOI：10.1002/anie.202012720

  日期：2021.3

  We describe a cerium‐catalyzed aerobic oxidative ring expansion for the expedient construction of synthetically challenging macrolactones under visible‐light conditions. Cyanoanthracene has been employed as co‐catalyst to accelerate the turnover of the cerium cycle leading to a fast conversion within 20 min of irradiation. Taking advantage of the high efficiency and operationally simple conditions

  我们描述了铈催化的好氧氧化环扩展，以在可见光条件下方便地合成具有挑战性的大内酯。氰基蒽已被用作助催化剂来加速铈循环的周转，从而在辐照后20分钟内实现快速转化。利用高效和操作简单的条件，已经从简单的构建基块中收集了100多种配备了9至19元大环的环系的大内酯。此外，已通过sonnerlactone的简明合成证明了该策略简化分子复杂性产生的潜在潜力。
• 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.