(4S,5S)-4-methyl-5-vinyl-2-oxazolone | 134210-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5S)-4-methyl-5-vinyl-2-oxazolone
• 英文别名: (4S,5S)-5-ethenyl-4-methyl-1,3-oxazolidin-2-one
• CAS: 134210-18-7
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: OAJZFTZXUQAADP-WHFBIAKZSA-N

物化性质

• 沸点：
  288.5±20.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl (2S)-3-hydroxypent-4-en-2-ylcarbamate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以79%的产率得到(4S,5S)-4-methyl-5-vinyl-2-oxazolone
  参考文献：
  名称：

  A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction

  摘要：

  A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.

  DOI：

  10.1021/jo00014a010

文献信息

• Highly Stereoselective Intramolecular S_N2′ Cyclization Yielding Chiral ­Oxazolidin-2-ones: General Route to α-Hydroxy-β-amino Acids
  作者：Ki Hun Park、Woo Duck Seo、Marcus J. Curtis-Long、Jin Hyo Kim、Jong Keun Park、Ki Min Park

  DOI：10.1055/s-2005-872264

  日期：——

  Intramolecular nucleophilic attack onto allylsulfonates promoted by silica gel acting as an acid catalyst provides expedient stereoselective access to 4,5-difunctionalized oxazolidin-2-ones. Precursors were prepared efficiently from enantiopure α-amino acids and subsequent manipulation of the oxazolidin-2-ones yielded enantiopure α-hydroxy-β-amino acids.

  硅胶作为酸催化剂促进对烯丙基磺酸盐的分子内亲核攻击提供了对 4,5-双官能化 2-酮的立体选择性访问。前体是由对映纯的 α-氨基酸有效制备的，随后对恶唑烷-2-酮的操作产生了对映纯的 α-羟基-β-氨基酸。
• <i>N</i>-Boc Amines to Oxazolidinones via Pd(II)/Bis-sulfoxide/Brønsted Acid Co-Catalyzed Allylic C–H Oxidation
  作者：Thomas J. Osberger、M. Christina White

  DOI：10.1021/ja506036q

  日期：2014.8.6

  A Pd(II)/bis-sulfoxide/Bronsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and pi-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.
• A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction
  作者：Toshiro Ibuka、Hiromu Habashita、Akira Otaka、Nobutaka Fujii、Yusaku Oguchi、Tadao Uyehara、Yoshinori Yamamoto

  DOI：10.1021/jo00014a010

  日期：1991.7

  A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.