| 40936-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• CAS: 40936-26-3
• 化学式: C₈H₁₆NO₂
• 分子量: 158.221
• InChiKey: JPLSVQGCJHINQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  13.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1-吡咯啉-N-氧化物 、 二乙氧基二硫醚 生成
  参考文献：
  名称：

  Photolysis of Dialkoxy Disulfides:  A Convenient Source of Alkoxy Radicals for Addition to the Sphere of Fullerene C₆₀

  摘要：

  Photolysis of dialkoxy disulfides ROSSOR (R = Me, Et, i-Pr, t-Bu, i-PrCH2, t-BuCH(2)) yields the radicals RO(.), ROS(.), and ROS(.)=O that were identified on the basis of product analysis and spin trapping techniques. It has been shown that only the alkoxy radicals RO(.), produced from ROSSOR, add to the sphere of fullerene C-60 in steady state conditions to yield the RO-C-60(.) adducts which can be detected by ESR spectroscopy. The different trend of the hydrogen splitting constants in the RO-C-60(.) with respect to the corresponding RS-C-60(.) adducts previously reported has been interpreted as a consequence of the different C-O and C-S bond lengths.

  DOI：

  10.1021/jo952169e

文献信息

• Microwave-assisted generation of alkoxyl radicals and their use in additions, β-fragmentations, and remote functionalizations
  作者：Jens Hartung、Kristina Daniel、Thomas Gottwald、Andreas Groß、Nina Schneiders

  DOI：10.1039/b603480b

  日期：——

  solvents affords alkoxyl radicals, which were identified by (i) spin adduct formation (EPR-spectroscopy) and (ii) fingerprint-type selectivities in intramolecular additions (stereoselective synthesis of disubstituted tetrahydrofurans), beta-fragmentations (formation of carbonyl compounds), and C,H-activation of aliphatic subunits, by delta-selective hydrogen atom transfer. C-Radicals formed from oxygen-centered

  N-（烷氧基）噻唑-2（3H）-硫酮在低吸收性溶剂中的微波辐射（2.45 GHz，300-500 W）提供烷氧基，其通过以下方法鉴定：（i）自旋加合物形成（EPR光谱）和（ii）通过δ-选择性氢原子转移在分子内加成（二取代的四氢呋喃的立体选择性合成），β-片段化（羰基化合物的形成）和脂族亚基的C，H-活化中的指纹类型选择性。由以氧为中心的中间体形成的C自由基被Bu（3）SnH，L-半胱氨酸乙酯，谷胱甘肽的还原形式（还原性俘获）捕获，或通过溴原子供体BrCCl（3）（杂原子功能化）进行研究结果表明，微波活化优于UV / Vis光解法和传导加热，可从N-（烷氧基）噻唑硫酮生成烷氧基自由基。到目前为止，它提供了最短的反应时间，并且可以显着减少捕集试剂的量。
• Formation of Hydroxyl Spin Adducts via Nucleophilic Addition--Oxidation to 5,5-Dimethyl-1-pyrroline N-Oxide (DMPO).
  作者：Lennart Eberson、Balin Balinov、Gunnar Hagelin、Harald Dugstad、Terje Thomassen、Benita H. Forngren、Tobias Forngren、Per Hartvig、Karin Markides、Ulrika Yngve、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0584

  日期：——

  The formation of the hydroxyl radical spin adduct of DMPO, HO DMPO, has been studied by EPR spectroscopy under conditions where the hydroxyl radical cannot be involved. One method was the photosensitized oxidation of DMPO to its radical cation. followed by reaction of the latter with water. This procedure worked well with sensitizers Sens (quinones) having triplet states with E degrees((T)Sens*/Sens(.-))>1.7 1.8V(SCE).The second method employed nucleophilic addition of water to DMPO, followed by reaction of the intermediate hydroxylamine by mild thermal oxidants (quinones, Fe-III) with redox potentials in the range -0.5 to 0.5 V. The observation of IIO DMPO. in this reaction was dependent on the acidity of the medium, since the relatively slow rate of formation of IIO DMPO. must be compensated for by a correspondingly longer half-life, tau(1/2). This is decreased by increasing acidity, and a lower limit of tau(1/2) was estimated at 1 1.5 min. The use of buffered neutral or slightly alkaline solutions or ethyl acetate as solvent satisfied this requirement.The nucleophilic mechanism, sometimes denoted the Forrester Hepburn mechanism, was also applicable to the reaction between normal alcohols and DMPO, giving rise to RO-DMPO.. A sterically demanding alcohol (t-BuOH) or electrophilic alcohols ( 2,2,2-trifluoroethanol or 1,1,1,3,3,3-hexafluoropropan-2-ol) required photochemical activation for reaction to occur.
• Photolysis of Dialkoxy Disulfides:  A Convenient Source of Alkoxy Radicals for Addition to the Sphere of Fullerene C₆₀
  作者：R. Borghi、L. Lunazzi、G. Placucci、G. Cerioni、A. Plumitallo

  DOI：10.1021/jo952169e

  日期：1996.1.1

  Photolysis of dialkoxy disulfides ROSSOR (R = Me, Et, i-Pr, t-Bu, i-PrCH2, t-BuCH(2)) yields the radicals RO(.), ROS(.), and ROS(.)=O that were identified on the basis of product analysis and spin trapping techniques. It has been shown that only the alkoxy radicals RO(.), produced from ROSSOR, add to the sphere of fullerene C-60 in steady state conditions to yield the RO-C-60(.) adducts which can be detected by ESR spectroscopy. The different trend of the hydrogen splitting constants in the RO-C-60(.) with respect to the corresponding RS-C-60(.) adducts previously reported has been interpreted as a consequence of the different C-O and C-S bond lengths.