tert-Butyl trans-(-)-2,3-epoxy-4-oxo-4-phenylbut-2-enoate | 186707-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl trans-(-)-2,3-epoxy-4-oxo-4-phenylbut-2-enoate
• 英文别名: tert-butyl (2R,3R)-3-benzoyloxirane-2-carboxylate
• CAS: 186707-60-8
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: LFUPVLVLCUJDLF-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-Butyl trans-(-)-2,3-epoxy-4-oxo-4-phenylbut-2-enoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以73%的产率得到2-O-tert-butyl 3-O-phenyl (2R,3R)-oxirane-2,3-dicarboxylate
  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：

  (E)-tert-butyl 4-oxo-4-phenylbut-2-enoate 在 sodium hydroxide 、 immobilised poly-L-leucine 、 双氧水 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以66%的产率得到tert-Butyl trans-(-)-2,3-epoxy-4-oxo-4-phenylbut-2-enoate
  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

• CHIEN, CHUN-SHENG;KAWASAKI, TOMOMI;SAKAMOTO, MASANORI;TAMURA, YASUMITSU;K+, CHEM. AND PHARM. BULL., 1985, 33, N 7, 2743-2749
  作者：CHIEN, CHUN-SHENG、KAWASAKI, TOMOMI、SAKAMOTO, MASANORI、TAMURA, YASUMITSU、K+

  DOI：——

  日期：——
• Development of the Juliá asymmetric epoxidation reaction. Part 2. Application of the oxidation to alkyl enones, enediones and unsaturated keto esters
  作者：Wolfgang Kroutil、M. Elena Lasterra-Sánchez、Samuel J. Maddrell、Patrick Mayon、Phillip Morgan、Stanley M. Roberts、Steven R. Thornton、Christine J. Todd、Melek Tüter

  DOI：10.1039/p19960002837

  日期：——

  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.
• 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.