(2R,3S)-3-[2-methyl-3-cyano-3-hydroxy-1-oxobutyl]-(S)-4-isopropyl-2-oxazolidinone | 623562-09-4

• 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: (2R,3S)-3-[2-methyl-3-cyano-3-hydroxy-1-oxobutyl]-(S)-4-isopropyl-2-oxazolidinone
• 英文别名: (2S,3R)-2-hydroxy-2,3-dimethyl-4-oxo-4-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]butanenitrile
• CAS: 623562-09-4
• 化学式: C₁₂H₁₈N₂O₄
• 分子量: 254.286
• InChiKey: SXCIEMINJPCRBC-YGOYTEALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  90.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-[2-methyl-3-cyano-3-hydroxy-1-oxobutyl]-(S)-4-isopropyl-2-oxazolidinone 在 镍 lithium hydroxide 、 氢气 、 双氧水 、 sodium acetate 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 63.0h， 生成 (2R,3S)-4-acetylamino-2,3-dimethyl-3-hydroxybutyric acid
  参考文献：
  名称：

  Highly diastereoselective addition of Et2AlCN to β-keto amides derived from (S)-4-isopropyl-2-oxazolidinone

  摘要：

  The addition of Et2AlCN in the presence of ZnBr2 or Et2AlCl to 1,3-dicarbonyl compounds derived from (S)-4-isopropyl-2-oxazolidinone, proceeds with high diastereoselectivity (94-98% de) and good chemical yields. This type of addition to chiral P-dicarbonyl substrates represents a new synthetic methodology leading to the formation of enantiomerically pure cyanohydrins. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.004
• 作为产物：
  描述：

  (S)-4-异丙基-3-丙酰基-2-恶唑烷酮 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 生成 (2R,3S)-3-[2-methyl-3-cyano-3-hydroxy-1-oxobutyl]-(S)-4-isopropyl-2-oxazolidinone
  参考文献：
  名称：

  Highly diastereoselective addition of Et2AlCN to β-keto amides derived from (S)-4-isopropyl-2-oxazolidinone

  摘要：

  The addition of Et2AlCN in the presence of ZnBr2 or Et2AlCl to 1,3-dicarbonyl compounds derived from (S)-4-isopropyl-2-oxazolidinone, proceeds with high diastereoselectivity (94-98% de) and good chemical yields. This type of addition to chiral P-dicarbonyl substrates represents a new synthetic methodology leading to the formation of enantiomerically pure cyanohydrins. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.004

文献信息

• Highly diastereoselective addition of Et2AlCN to β-keto amides derived from (S)-4-isopropyl-2-oxazolidinone
  作者：Virginia Flores-Morales、Mario Fernández-Zertuche、Mario Ordóñez

  DOI：10.1016/j.tetasy.2003.07.004

  日期：2003.9

  The addition of Et2AlCN in the presence of ZnBr2 or Et2AlCl to 1,3-dicarbonyl compounds derived from (S)-4-isopropyl-2-oxazolidinone, proceeds with high diastereoselectivity (94-98% de) and good chemical yields. This type of addition to chiral P-dicarbonyl substrates represents a new synthetic methodology leading to the formation of enantiomerically pure cyanohydrins. (C) 2003 Elsevier Ltd. All rights reserved.