5c-methyl-2-oxo-oxazolidine-4r-carboxylic acid ethyl ester | 89775-95-1

• 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: 5c-methyl-2-oxo-oxazolidine-4r-carboxylic acid ethyl ester
• 英文别名: N,O-carbonyl-DL-allothreonine ethyl ester；ethyl (4S,5S)-5-methyl-2-oxo-1,3-oxazolidine-4-carboxylate
• CAS: 89775-95-1
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: RYPLXODFRHLRQV-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5c-methyl-2-oxo-oxazolidine-4r-carboxylic acid ethyl ester 在 4-二甲氨基吡啶 作用下， 生成 (4S,5S)-3-Acetyl-5-methyl-2-oxo-oxazolidine-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 4-carboethoxy-4-oxazolin-2-ones from 3-nosyloxy-2-ketoesters

  摘要：

  3-Nosyloxy-2-ketoesters, available from 2-ketoesters, react efficiently with methyl carbamate and tosic acid in refluxing toluene to provide 4-carboalkoxy-4-oxazolin-2-ones in good yields (41-84%). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10854-1
• 作为产物：
  描述：

  光气 、 ethyl 2-amino-3-hydroxybutanoate 生成 5c-methyl-2-oxo-oxazolidine-4r-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 4-carboethoxy-4-oxazolin-2-ones from 3-nosyloxy-2-ketoesters

  摘要：

  3-Nosyloxy-2-ketoesters, available from 2-ketoesters, react efficiently with methyl carbamate and tosic acid in refluxing toluene to provide 4-carboalkoxy-4-oxazolin-2-ones in good yields (41-84%). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10854-1

文献信息

• Carbon Dioxide as a Carbonylating Agent in the Synthesis of 2-Oxazolidinones, 2-Oxazinones, and Cyclic Ureas: Scope and Limitations
  作者：Jairo Paz、Carlos Pérez-Balado、Beatriz Iglesias、Luis Muñoz

  DOI：10.1021/jo100268n

  日期：2010.5.7

  Carbon dioxide can be used as a convenient carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas. The transient carbamate anion generated by treating a primary or secondary amine group in basic media can be activated with phosphorylating agents such as Diphenylphosphoryl azide (DPPA) and Diphenyl chlorophosphate (DPPCl) but also with other types of electrophiles such

  在2-恶唑烷酮，2-恶嗪酮和环状脲的合成中，二氧化碳可用作方便的羰基化剂。通过在碱性介质中处理伯胺或仲胺基团而生成的瞬态氨基甲酸酯阴离子可以用磷酸化剂（如二苯基磷酰叠氮化物（DPPA）和二苯基氯代磷酸酯（DPPC1））活化，也可以用其他类型的亲电试剂（如SOCl 2，TsCl或氯化铝。羟基将活化的氨基甲酸酯分子内捕获导致形成2-恶唑烷酮或2-恶嗪酮，产率高至优异。该方法已成功地用于从相应的二胺合成高达7元环的环状脲。
• Synthesis of 4-carboethoxy-4-oxazolin-2-ones from 3-nosyloxy-2-ketoesters
  作者：Robert V. Hoffman、M.Catherine Johnson、John F. Okonya

  DOI：10.1016/s0040-4039(97)10854-1

  日期：1998.3

  3-Nosyloxy-2-ketoesters, available from 2-ketoesters, react efficiently with methyl carbamate and tosic acid in refluxing toluene to provide 4-carboalkoxy-4-oxazolin-2-ones in good yields (41-84%). (C) 1998 Elsevier Science Ltd. All rights reserved.