methyl 3-[(2S)-1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]pyrrolidin-2-yl]propanoate | 1126897-31-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-[(2S)-1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]pyrrolidin-2-yl]propanoate
• CAS: 1126897-31-1
• 化学式: C₁₈H₂₄N₂O₄
• 分子量: 332.4
• InChiKey: YDRVXGCCYAHRCJ-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-氯-3-碘丙烷 、 在 indium(III) chloride 、 羰基镁 作用下， 以 二氯甲烷 为溶剂， 反应 67.0h， 以15%的产率得到methyl (4R)-4-[[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]amino]-7-chloroheptanoate
  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 γ-Amino Esters via Mn-Mediated Radical Addition to Chiral γ-Hydrazonoesters
  作者：Gregory K. Friestad、Koushik Banerjee

  DOI：10.1021/ol802932v

  日期：2009.3.5

  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.