(4R, 5S)-4-benzyl-5-(1,2-bis(isopropoxycarbonyl)hydrazino)-2-oxazolidinone | 142618-91-5

• 分子结构分类: 有机化合物
• 英文名称: (4R, 5S)-4-benzyl-5-(1,2-bis(isopropoxycarbonyl)hydrazino)-2-oxazolidinone
• 英文别名: propan-2-yl N-[(4R,5S)-4-benzyl-2-oxo-1,3-oxazolidin-5-yl]-N-(propan-2-yloxycarbonylamino)carbamate
• CAS: 142618-91-5
• 化学式: C₁₈H₂₅N₃O₆
• 分子量: 379.413
• InChiKey: CPQJMBUUTZGWCE-CABCVRRESA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106.2
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R, 5S)-4-benzyl-5-(1,2-bis(isopropoxycarbonyl)hydrazino)-2-oxazolidinone 在 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (R)-4-苄基-2-噁唑烷酮
  参考文献：
  名称：

  Chiral electrophilic “glycinal” equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones

  摘要：

  The thermal reaction of 3-[(IS)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as alpha-aminoaldehyde templates useful for the synthesis of a wide variety of optically active alpha-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01077-0
• 作为产物：
  描述：

  diisopropyl azodicarboxylate 在 甲醇 、 锂硼氢 、 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 16.05h， 生成 (4R, 5S)-4-benzyl-5-(1,2-bis(isopropoxycarbonyl)hydrazino)-2-oxazolidinone
  参考文献：
  名称：

  Chiral electrophilic “glycinal” equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones

  摘要：

  The thermal reaction of 3-[(IS)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as alpha-aminoaldehyde templates useful for the synthesis of a wide variety of optically active alpha-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01077-0