N-acetyl-threo-α-amino-β-hydroxy-n-butyric acid ethyl ester | 69625-24-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyl-threo-α-amino-β-hydroxy-n-butyric acid ethyl ester
• 英文别名: L-threo (2S,3R) Ethyl 2-acetamido-3-hydroxybutyrate；(2S,3R)-ethyl 2-acetamido-3-hydroxybutanoate；N-acetyl-L-threonine ethyl ester；ethyl (2S,3R)-2-acetamido-3-hydroxybutanoate
• CAS: 69625-24-7
• 化学式: C₈H₁₅NO₄
• 分子量: 189.211
• InChiKey: BGBUNNHXCHSBQT-VDTYLAMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetyl-threo-α-amino-β-hydroxy-n-butyric acid ethyl ester 在 氨 作用下， 以 乙醇 为溶剂， 生成 N-acetyl-L-threoninamide 、 ammonium N-acetyl-threo-α-amino-β-hydroxy-n-butyrate
  参考文献：
  名称：

  AmmoniumN-acetyl-L-threoninate and methylammoniumN-acetyl-L-threoninate

  摘要：

  DOI：

  10.1107/s0108270100001268
• 作为产物：
  描述：

  2-(羟亚氨基)乙酰乙酸乙酯 在 palladium on activated charcoal (-)-CHIRAPHOS*RuBr₂ 、 氢气 作用下， 以 甲醇 、 丙酮 为溶剂， 20.0 ℃ 、9.12 MPa 条件下， 生成 N-acetyl-threo-α-amino-β-hydroxy-n-butyric acid ethyl ester
  参考文献：
  名称：

  Asymmetric synthesis. Practical production of D and L threonine. Dynamic kinetic resolution in rhodium and ruthenium catalyzed hydrogenation of 2-acylamino-3-oxobutyrates.

  摘要：

  Enantioselective syntheses of D and L threonine are described. Racemic methyl and ethyl 2-acylamino-3-oxobutyrate 1 were synthesized from the corresponding acetoacetates 6 and then hydrogenated stereoselectively via dynamic kinetic resolution with various chiral P * P Rh (I) 8 and Ru (II) 10 catalysts to give syn optically active alcohols which could be converted by hydrolysis and treatment with propylene oxide into threonine. The best results were obtained using (-) CHIRAPHOS Ru and (+) BINAP Ru as catalysts, in the hydrogenation step leading respectively to D threonine (ee: 99 %) and L threonine (ee: 94 %) in 26-34 % overall yields.

  DOI：

  10.1016/s0957-4166(00)86108-x

文献信息

• ANTI-ODOR COMPOSITIONS AND THERAPEUTIC USE
  申请人：Yu J. Ruey

  公开号：US20060251597A1

  公开（公告）日：2006-11-09

  This application discloses a composition comprising a malodor compound and an anti-odor ingredient effective for reducing the presence or production of malodor. The composition may be topically applied to a subject and is useful for cosmetic conditions, pharmaceutical indications, or other objectives.

  本申请公开了一种包含恶臭化合物和抑臭成分的组合物，用于减少恶臭的存在或产生。该组合物可以局部应用于一个对象，并且适用于化妆条件、药用指示或其他目的。
• Han, Hyunsoo; Cho, Chang-Woo; Janda, Kim D., Chemistry - A European Journal, 1999, vol. 5, # 5, p. 1565 - 1569
  作者：Han, Hyunsoo、Cho, Chang-Woo、Janda, Kim D.

  DOI：——

  日期：——
• Kato, Nobuo; Fujie, Masayoshi; Hasegawa, Masayasu, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 2, p. 303 - 307
  作者：Kato, Nobuo、Fujie, Masayoshi、Hasegawa, Masayasu、Shimao, Masayuki、Kita, Keiko、Yanase, Hideshi

  DOI：——

  日期：——
• [EN] ANTI-ODOR COMPOSITIONS AND THERAPEUTIC USE<br/>[FR] COMPOSITIONS ANTI-ODEURS ET UTILISATION THERAPEUTIQUE ASSOCIEE
  申请人：YU RUEY J

  公开号：WO2006119283A2

  公开（公告）日：2006-11-09

  [EN] This application discloses a composition comprising a malodor compound and an anti-odor ingredient effective for reducing the presence or production of malodor. The composition may be topically applied to a subject and is useful for cosmetic conditions, pharmaceutical indications, or other objectives.
  [FR] L'invention concerne une composition contenant un composé malodorant et un ingrédient anti-odeurs permettant de réduire la présence ou la fabrication de mauvaises odeurs. Cette composition peut être topiquement appliquée sur un sujet et est utile dans le domaine cosmétique, pharmaceutique ou dans d'autres domaines.
• Asymmetric synthesis. Practical production of D and L threonine. Dynamic kinetic resolution in rhodium and ruthenium catalyzed hydrogenation of 2-acylamino-3-oxobutyrates.
  作者：J.P. Genet、C. Pinel、S. Mallart、S. Juge、S. Thorimbert、J.A. Laffitte

  DOI：10.1016/s0957-4166(00)86108-x

  日期：1991.1

  Enantioselective syntheses of D and L threonine are described. Racemic methyl and ethyl 2-acylamino-3-oxobutyrate 1 were synthesized from the corresponding acetoacetates 6 and then hydrogenated stereoselectively via dynamic kinetic resolution with various chiral P * P Rh (I) 8 and Ru (II) 10 catalysts to give syn optically active alcohols which could be converted by hydrolysis and treatment with propylene oxide into threonine. The best results were obtained using (-) CHIRAPHOS Ru and (+) BINAP Ru as catalysts, in the hydrogenation step leading respectively to D threonine (ee: 99 %) and L threonine (ee: 94 %) in 26-34 % overall yields.