3-(mesyloxy)-2,4-pentadienone | 111793-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(mesyloxy)-2,4-pentadienone
• 英文别名: α-mesyloxy-2,4-pentadione；1-Acetyl-2-oxopropyl methanesulfonate；2,4-dioxopentan-3-yl methanesulfonate
• CAS: 111793-44-3
• 化学式: C₆H₁₀O₅S
• 分子量: 194.208
• InChiKey: RLNGXDJRFNJHDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  [羟基(甲烷磺酰氧基)碘代]苯 、 乙酰丙酮 以60%的产率得到
  参考文献：
  名称：

  LODAYA, JAYANT S.;KOSER, GERALD F., J. ORG. CHEM., 53,(1988) N 1, 210-212

  摘要：

  DOI：

文献信息

• Solvent-Free Reactions with Hypervalent Iodine Reagents
  作者：Mekhman S. Yusubov、Thomas Wirth

  DOI：10.1021/ol047363e

  日期：2005.2.1

  [reaction: see text] We describe solvent-free reactions for the synthesis of hypervalent iodine reagents and their use in solid-state reactions. Improved yields and higher purities of the products are observed.

  [反应：见正文]我们描述了用于合成高价碘试剂的无溶剂反应及其在固态反应中的用途。观察到产物的产率提高和纯度更高。
• A New Application of Hypervalent Iodine (λ⁵) Reagents with Organosulfonic Acids for Direct α-Organosulfonyloxylation Carbonyl Compounds
  作者：Krishnacharya Akamanchi、Ulhas Mahajan

  DOI：10.1055/s-2008-1072508

  日期：——

  Hypervalent iodine (λ 5 ) reagents in combination with P-toluenesulfonic acid when reacted with ketones under reflux temperature in acetonitrile gave α-tosyloxy ketones in moderate to excellent yields. The reaction was developed further for both ketones and dicarbonyl compounds using Dess-Martin periodinane reagent in combination with P-toluenesulfonic acid and methanesulfonic acid, to give mono-α-tosyloxy

  当在回流温度下在乙腈中与酮反应时，高价碘 (λ 5 ) 试剂与对甲苯磺酸结合，以中等至极好的收率得到 α-甲苯磺酰氧基酮。使用 Dess-Martin 高碘烷试剂与对甲苯磺酸和甲磺酸结合，进一步开发了酮和二羰基化合物的反应，以非常高的收率得到单-α-甲苯磺酰氧基和单-α-甲磺酰氧基产物。
• Hypervalent iodine oxidation: α-Functionalization of β-dicarbonyl compounds using iodosobenzene
  作者：Robert M. Moriarty、Radhe K. Vaid、Vasulinga T. Ravikumar、Beena K. Vaid、Thomas E. Hopkins

  DOI：10.1016/s0040-4020(01)86720-x

  日期：1988.1

  Hypervalent iodine oxidation of β-diketones and β-ketoesters with iodosobenzene-boron trifluoride etherate in chloroform using appropriate nucleophiles results In α-functionalization. Benzoylacetone on reaction with iodosobenzene or iodosobenzene boron trifluoride-etherate in methanol yields α-methoxyacetophenone () and methyl phenylacetate (). The possible mechanisms for these reactions are discussed

  使用适当的亲核试剂，在氯仿中用碘代苯硼三氟化硼醚化物将β-二酮和β-酮​​酸酯的高价碘氧化可导致α-官能化。在甲醇中与碘代苯或碘代苯三氟化硼-醚化物反应生成苯甲酰丙酮，生成α-甲氧基苯乙酮（）和苯乙酸甲酯（）。讨论了这些反应的可能机理。
• <i>m</i>-Iodosylbenzoic Acid: Recyclable Hypervalent Iodine Reagent for <font>α</font>-Tosyloxylation and <font>α</font>-Mesyloxylation of Ketones
  作者：Mekhman S. Yusubov、Tatyana V. Funk、Roza Y. Yusubova、Galina Zholobova、Andreas Kirschning、Joo Yeon Park、Ki-Whan Chi

  DOI：10.1080/00397910902838870

  日期：2009.10.12

  m-Iodosylbenzoic acid-mediated reactions of various carbonyl compounds provided -organosulfonyloxy carbonyl compounds in good yields. The final products could be easily isolated without any chromatographic purification by simple treatment of the crude mixture with an anionic exchange resin.
• Direct .alpha.-mesyloxylation of ketones and .beta.-dicarbonyl compounds with [hydroxy(mesyloxy)iodo]benzene
  作者：Jayant S. Lodaya、Gerald F. Koser

  DOI：10.1021/jo00236a048

  日期：1988.1