Methyl (2S)-4-oxo-2-(phenylmethoxy)butanoate | 667917-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl (2S)-4-oxo-2-(phenylmethoxy)butanoate
• 英文别名: methyl (2S)-4-oxo-2-phenylmethoxybutanoate
• CAS: 667917-01-3
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: BPJWIBCMSQAZBC-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-3-amino-4-benzyl-1,3-oxazolan-2-one 、 Methyl (2S)-4-oxo-2-(phenylmethoxy)butanoate 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 C₂₂H₂₄N₂O₅ 、 C₂₂H₂₄N₂O₅
  参考文献：
  名称：

  Synthesis of γ-Amino Esters via Mn-Mediated Radical Addition to Chiral γ-Hydrazonoesters

  摘要：

  Highly stereoselective Mn-mediated couplings of alkyl iodides with chiral N-acylhydrazones bearing ester functionality afford a series of gamma-hydrazino esters, including gamma-substituted, alpha,gamma-disubstituted, and alpha,alpha,gamma-trisubstituted examples. In contrast to prior work with chiral N-acylhydrazones, high stereoselectivity was observed even in the absence of Lewis acid. Microwave-assisted acylation with trifluoroacetic anhydride and reductive N-N bond cleavage provided the gamma-amino ester functionality in a synthetically useful N-TFA-protected form.

  DOI：

  10.1021/ol802932v
• 作为产物：
  描述：

  (2S)-2-benzyloxy-4-pentenoic acid methyl ester 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以73%的产率得到Methyl (2S)-4-oxo-2-(phenylmethoxy)butanoate
  参考文献：
  名称：

  Synthesis of γ-Amino Esters via Mn-Mediated Radical Addition to Chiral γ-Hydrazonoesters

  摘要：

  Highly stereoselective Mn-mediated couplings of alkyl iodides with chiral N-acylhydrazones bearing ester functionality afford a series of gamma-hydrazino esters, including gamma-substituted, alpha,gamma-disubstituted, and alpha,alpha,gamma-trisubstituted examples. In contrast to prior work with chiral N-acylhydrazones, high stereoselectivity was observed even in the absence of Lewis acid. Microwave-assisted acylation with trifluoroacetic anhydride and reductive N-N bond cleavage provided the gamma-amino ester functionality in a synthetically useful N-TFA-protected form.

  DOI：

  10.1021/ol802932v

文献信息

• Synthesis of a 5-oxo-2-Tetrahydrofuranyl Derivative of an Evans Auxiliary via a Novel Reaction Induced by Nucleophiles
  作者：Yikang Wu、Liang Li、Ya-Ping Sun

  DOI：10.1055/s-2003-43339

  日期：——

  A 5-oxo-2-tetrahydrofuranyl derivative of an Evans auxiliary could be obtained through a previously unknown ‘rearrangement’ of the oxazolidinone moiety in an α-benzoxy-γ-aldehyde acyl oxazolidinone in 60-97% yields on treatment with a range of ­nucleophiles.

  通过对δ-苯氧δ-醛酰基噁唑烷酮中的噁唑烷酮分子进行之前未知的 "重排"，可以获得一种埃文斯助剂的 5-氧代-2-四氢呋喃基衍生物，在一系列亲核剂的作用下，产率为 60-97%。