(5R,4S)-4-methyl-5-vinyl-2-oxazolone | 134210-19-8

• 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: (5R,4S)-4-methyl-5-vinyl-2-oxazolone
• 英文别名: (4S,5R)-5-ethenyl-4-methyl-1,3-oxazolidin-2-one
• CAS: 134210-19-8
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: OAJZFTZXUQAADP-CRCLSJGQSA-N

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93%的产率得到(5R,4S)-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。
• Oxazolidinones as taro inhibitors
  申请人：MERCK SHARP & DOHME CORP.

  公开号：US11141410B2

  公开（公告）日：2021-10-12

  Novel compounds of the structural formula I, and the pharmaceutically acceptable salts thereof, are inhibitors of TarO and may be useful in the prevention, treatment and suppression of diseases mediated by TarO, such as bacterial infections, including gram negative bacterial infections and gram positive bacterial infections such as MRSA and MRSE, alone or in combination with a β-lactam antibiotic.

  结构式 I 的新型化合物及其药学上可接受的盐类是 TarO 的抑制剂，可用于预防、治疗和抑制由 TarO 介导的疾病，如细菌感染，包括革兰氏阴性细菌感染和革兰氏阳性细菌感染，如 MRSA 和 MRSE，可单独使用或与β-内酰胺类抗生素联合使用。
• OXAZOLIDINONES AS TARO INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP3402777A1

  公开（公告）日：2018-11-21
• [EN] OXAZOLIDINONES AS TARO INHIBITORS<br/>[FR] UTILISATION D'OXAZOLIDONES EN TANT QU'INHIBITEURS DE TARO
  申请人：MERCK SHARP & DOHME

  公开号：WO2017106138A1

  公开（公告）日：2017-06-22

  Novel compounds of the structural formula I, and the pharmaceutically acceptable salts thereof, are inhibitors of TarO and may be useful in the prevention, treatment and suppression of diseases mediated by TarO, such as bacterial infections, including gram negative bacterial infections and gram positive bacterial infections such as MRSA and MRSE, alone or in combination with a β-lactam antibiotic.
• 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.