trans-(-)-1,4-Di-tert-butyl-2,3-epoxybutane-1,4-dione | 186707-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-(-)-1,4-Di-tert-butyl-2,3-epoxybutane-1,4-dione
• 英文别名: 1-[(2R,3R)-3-(2,2-dimethylpropanoyl)oxiran-2-yl]-2,2-dimethylpropan-1-one
• CAS: 186707-61-9
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: MWVTUHPZQJAOSH-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-(-)-1,4-Di-tert-butyl-2,3-epoxybutane-1,4-dione 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以76%的产率得到(2R,3R)-Oxirane-2,3-dicarboxylic acid di-tert-butyl ester
  参考文献：
  名称：

  Development of the Juliá asymmetric epoxidation reaction. Part 2. Application of the oxidation to alkyl enones, enediones and unsaturated keto esters

  摘要：

  Polyleucine-based systems have been used to catalyse the asymmetric oxidation of a variety of alkyl enones 1-4,9-14, an enynone 16 and a dienone 17 to afford the corresponding epoxides 5-8, 18-26 in good to excellent yield and optical purity. A range of enediones 30-32, 34 and one unsaturated keto ester 33 have also been epoxidised stereoselectively to afford optically active epoxides 35-39. The epoxidations were carried out with basic peroxide as the oxidant; the polyleucine catalyst was prepared from leucine N-carboxyanhydride using 1,3-diaminopropane, water (employing a humidity cabinet) or a polystyrene immobilised amine as the initiator. Preliminary mass spectral data on material derived from L-leucine and 1,3-diaminopropane (DAP-PLL) suggest that the catalyst consists of material that contains 22 +/- 10 leucine residues.

  DOI：

  10.1039/p19960002837
• 作为产物：
  描述：

  1-溴频哪酮 在 sodium hydroxide 、 二乙基羟胺 、 immobilised poly-L-leucine 、 potassium tert-butylate 、 双氧水 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 48.0h， 生成 trans-(-)-1,4-Di-tert-butyl-2,3-epoxybutane-1,4-dione
  参考文献：
  名称：

  Development of the Juliá asymmetric epoxidation reaction. Part 2. Application of the oxidation to alkyl enones, enediones and unsaturated keto esters

  摘要：

  Polyleucine-based systems have been used to catalyse the asymmetric oxidation of a variety of alkyl enones 1-4,9-14, an enynone 16 and a dienone 17 to afford the corresponding epoxides 5-8, 18-26 in good to excellent yield and optical purity. A range of enediones 30-32, 34 and one unsaturated keto ester 33 have also been epoxidised stereoselectively to afford optically active epoxides 35-39. The epoxidations were carried out with basic peroxide as the oxidant; the polyleucine catalyst was prepared from leucine N-carboxyanhydride using 1,3-diaminopropane, water (employing a humidity cabinet) or a polystyrene immobilised amine as the initiator. Preliminary mass spectral data on material derived from L-leucine and 1,3-diaminopropane (DAP-PLL) suggest that the catalyst consists of material that contains 22 +/- 10 leucine residues.

  DOI：

  10.1039/p19960002837

文献信息

• Unexpected asymmetric epoxidation reactions catalysed by polyleucine-based systems
  作者：Wolfgang Kroutil、Patrick Mayon、M. Elena Lasterra-Sánchez、Samuel J. Maddrell、Stanley M. Roberts、Steven R. Thornton、Christine J. Todd、Melek Tüter

  DOI：10.1039/cc9960000845

  日期：——

  Polyleucine-based systems have been shown to catalyse the asymmetric epoxidation of a variety of enones, an enynone, selected enediones and an unsaturated ketoester.