N-acetyl-D-cycloserine | 51541-30-1

• 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-D-cycloserine
• 英文别名: (R)-4-acetylamino-isoxazolidin-3-one；N-((R)-3-oxo-isoxazolidin-4-yl)-acetamide；N-((R)-3-Oxo-isoxazolidin-4-yl)-acetamid；N-Acetyl-cycloserin；N²-acetyl-D-cycloserine；Acetamide, N-(3-oxo-4-isoxazolidinyl)-, (R)-；N-[(4R)-3-oxo-1,2-oxazolidin-4-yl]acetamide
• CAS: 51541-30-1
• 化学式: C₅H₈N₂O₃
• 分子量: 144.13
• InChiKey: LRLUMFQYCZKIPN-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 N-acetyl-D-cycloserine 在 碳酸氢钠 作用下， 生成 (4-acetamido-4,5-dihydro-1,2-oxazol-3-yl) 4-methylbenzenesulfonate
  参考文献：
  名称：

  环丝氨酸衍生物的核磁共振和质谱

  摘要：

  根据NMR光谱数据，表明N-乙酰基环丝氨酸的3-异恶唑烷酮环的乙酰化在氮上发生，而磺酰化在羰基氧上发生。将双键引入杂环导致的构象变化（二面角）反映在ABX系统参数的一致位移中。就动力学控制与热力学控制而言，酰化位点的变化被认为是可解释的。环丝氨酸的各种衍生物的质谱显示与指定的结构兼容。讨论了4-氨基-3-异恶唑烷酮系统碎裂的一些异常模式。

  DOI：

  10.1016/s0040-4020(01)83287-7
• 作为产物：
  描述：

  (R)-3-benzyloxy-4-acetylamino-Δ²-isoxazoline 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以88%的产率得到N-acetyl-D-cycloserine
  参考文献：
  名称：

  Chemoenzymatic synthesis of acetyl (R)-(+)- and (S)-(−)-cycloserine

  摘要：

  The two enantiomers of acetyl cycloserine 8, the immediate precursors of the chiral forms of cycloserine 1, were prepared in enantiomeric excess higher than 98% by means of lipase-catalyzed hydrolysis of 3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate (+/-)-5. Among the five lipases tested, lipase from Chromobacterium viscosum was by far the most selective catalyst. Since the enantiomeric ratio (E) of the reaction was higher than 100, the hydrolysis spontaneously stopped at 50% conversion to yield (R)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline [(R)-(+)-4] and (S)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate [(S)-(-)-5] in almost enantiomerically pure form. Intermediates (R)-(+)-4 and (S)-(-)-5 were transformed into the enantiomers of acetyl cycloserine through a four step sequence. This strategy constitutes a valid alternative to the previously reported procedures.

  DOI：

  10.1016/s0957-4166(00)80156-1

文献信息

• Benzamido and acetamido 4-amino-3-isoxazolidones and alkylated derivatives
  申请人：MERCK &

  公开号：US02845432A1

  公开（公告）日：1958-07-29
• STRUCTURE AND REACTIONS OF CYCLOSERINE¹
  作者：Phil H. Hidy、E. B. Hodge、Vernon V. Young、Roger L. Harned、Glenn A. Brewer、W. F. Phillips、W. F. Runge、Homer E. Stavely、A. Pohland、H. Boaz、H. R. Sullivan

  DOI：10.1021/ja01613a106

  日期：1955.4
• Mitsui; Imaizumi, Nippon Kagaku Zasshi, 1957, vol. 78, p. 812
  作者：Mitsui、Imaizumi

  DOI：——

  日期：——
• Chemoenzymatic synthesis of acetyl (R)-(+)- and (S)-(−)-cycloserine
  作者：Marco de Amici、Carlo de Micheli、Francesca Cateni、Giacomo Carrea、Gianluca Ottolina

  DOI：10.1016/s0957-4166(00)80156-1

  日期：1993.5

  The two enantiomers of acetyl cycloserine 8, the immediate precursors of the chiral forms of cycloserine 1, were prepared in enantiomeric excess higher than 98% by means of lipase-catalyzed hydrolysis of 3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate (+/-)-5. Among the five lipases tested, lipase from Chromobacterium viscosum was by far the most selective catalyst. Since the enantiomeric ratio (E) of the reaction was higher than 100, the hydrolysis spontaneously stopped at 50% conversion to yield (R)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline [(R)-(+)-4] and (S)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate [(S)-(-)-5] in almost enantiomerically pure form. Intermediates (R)-(+)-4 and (S)-(-)-5 were transformed into the enantiomers of acetyl cycloserine through a four step sequence. This strategy constitutes a valid alternative to the previously reported procedures.
• The nuclear magnetic resonance and mass spectra of derivatives of cycloserine
  作者：G.W.A. Milne、L.A. Cohen

  DOI：10.1016/s0040-4020(01)83287-7

  日期：1967.1

  parameters of the ABX system. Variation in the site of acylation is considered explicable in terms of kinetic vs. thermodynamic control. The mass spectra of various derivatives of cycloserine are shown to be compatible with the assigned structures. Some unusual modes of fragmentation of the 4-amino-3-isoxazolidone system are discussed.

  根据NMR光谱数据，表明N-乙酰基环丝氨酸的3-异恶唑烷酮环的乙酰化在氮上发生，而磺酰化在羰基氧上发生。将双键引入杂环导致的构象变化（二面角）反映在ABX系统参数的一致位移中。就动力学控制与热力学控制而言，酰化位点的变化被认为是可解释的。环丝氨酸的各种衍生物的质谱显示与指定的结构兼容。讨论了4-氨基-3-异恶唑烷酮系统碎裂的一些异常模式。