(4S,5R)-4-Methoxy-5-methyl-2-oxazolidinone | 122762-39-4

• 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: (4S,5R)-4-Methoxy-5-methyl-2-oxazolidinone
• 英文别名: (4S,5R)-4-Methoxy-5-methyl-oxazolidin-2-on；(4S,5R)-4-methoxy-5-methyl-1,3-oxazolidin-2-one
• CAS: 122762-39-4
• 化学式: C₅H₉NO₃
• 分子量: 131.131
• InChiKey: GNZHLRJPEHPTKQ-DMTCNVIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4RS,5R)-4-methoxy-5-methyl-1,3-oxazolidin-2-one 生成 (4S,5R)-4-Methoxy-5-methyl-2-oxazolidinone
  参考文献：
  名称：

  Zietlow Andrea, Steckhan Eberhard, J. Org. Chem., 59 (1994) N 19, S 5658-5661

  摘要：

  DOI：

文献信息

• Diastereoselective Amidoalkylation Reactions of Electrochemically Methoxylated Chiral 2-Oxazolidinones with Organocopper Reagents
  作者：Andrea Zietlow、Eberhard Steckhan

  DOI：10.1021/jo00098a025

  日期：1994.9

  (4RS,5R)-4-Methoxy-5-methyl-2-oxazolidinone (2ab), easily obtained by electrochemical decarboxylative methoxylation of the cyclic L-threonine derivative (4S,5R)-5-methyl-2-oxzolidinone-4-carboxylic acid (1), acts as effective diastereoselective amidoalkylation reagent. The methoxy group exchange in 2ab can be performed with higher order organocuprates (R(3)Cu(2)Li) in the presence of BF3.OEt(2). The 4-alkyl- or 4-aryl-substituted 2-oxazolidinones 3-6 can be obtained with trans diastereoselectivities between 75 and 98% in S(N)1 fashion via the intermediate N-acylimine. On the contrary, the N-methylated (4RS,5R)-4-methoxy-3,5-dimethyl-2-oxzolidinone (7ab) undergoes methoxy group exchange under identical conditions mainly via the S(N)2 mechanism. Thus, starting from trans-7a mainly cis-8b is formed with 76% ds. The described procedures make cis- or trans-4-alkyl-5-methyl-2-oxazolidinones and the respective dichiral 2-amino alcohols selectively available by a short reaction sequence.

  (4RS,5R)-4-甲氧基-5-甲基-2-氧杂环丁酮 (2ab) 可通过电化学脱羧甲氧基化反应方便地由环状 L-苏糖衍生物 (4S,5R)-5-甲基-2-氧杂环丁酮-4-羧酸 (1) 制得，它作为一种高效的非对映选择性胺基烷基化试剂。2ab 中的甲氧基交换反应可以在 BF3.OEt2 的存在下使用更高价态的有机铜试剂 (R(3)Cu(2)Li) 进行。通过 N-酰亚胺中间体，在 S(N)1 机制下，以 75 到 98% 的反式非对映选择性可获得 4-烷基或 4-芳基取代的 2-氧杂环丁酮 3-6。相反，N-甲基化的 (4RS,5R)-4-甲氧基-3,5-二甲基-2-氧杂环丁酮 (7ab) 在相同条件下主要通过 S(N)2 机制进行甲氧基交换。因此，从反式-7a 主要生成顺式-8b，非对映选择性为 76%。所述的程序通过短反应序列，选择性地提供顺式或反式的 4-烷基-5-甲基-2-氧杂环丁酮及其相应的双手性 2-氨基醇。
• Herborn, Christiane; Zietlow, Andrea; Steckhan, Eberhard, Angewandte Chemie, 1989, vol. 101, # 10, p. 1392 - 1394
  作者：Herborn, Christiane、Zietlow, Andrea、Steckhan, Eberhard

  DOI：——

  日期：——
• Zietlow Andrea, Steckhan Eberhard, J. Org. Chem., 59 (1994) N 19, S 5658-5661
  作者：Zietlow Andrea, Steckhan Eberhard

  DOI：——

  日期：——