(4R,5S)-3-((2'S)-2'-allyl-1'-oxononanoyl)-5-phenyl-4-methyl-2-oxazolidinone | 350991-12-7

• 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: (4R,5S)-3-((2'S)-2'-allyl-1'-oxononanoyl)-5-phenyl-4-methyl-2-oxazolidinone
• 英文别名: (4R,5S)-4-methyl-5-phenyl-3-[(2S)-2-prop-2-enylnonanoyl]-1,3-oxazolidin-2-one
• CAS: 350991-12-7
• 化学式: C₂₂H₃₁NO₃
• 分子量: 357.493
• InChiKey: NILJFKDJAFHNJN-MISYRCLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-((2'S)-2'-allyl-1'-oxononanoyl)-5-phenyl-4-methyl-2-oxazolidinone 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(2S)-2-allylnonanoic acid
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Minalemine A, a Guanidine Peptide from the Marine Tunicate Didemnum rodriguesi

  摘要：

  The total synthesis of the 3S,2S and 3R,2S diastereomers (1a and 1b) of minalemine A and the identification of the natural compound as the 3R,2S isomer is described. The key step in the synthesis is the preparation of the two enantiomers of the beta -amino diacid 3-(N-carboxymethyl)-aminodecanoic acid (Ncma), which were obtained by stereoselective alkylation with allyl bromide of two nonanoic acid imides bearing chiral oxazolidinones as chiral auxiliaries. Natural minalemine A shows identical (1)H NMR and very similar (13)C NMR spectra compared to the two synthetic diastereomers. Sufficient differences in their chromatographic behavior to allow conclusive identification were not found. However, the corresponding N-2-naphthoyl amides presented quite distinct circular dichroism spectra (CD), and these confirmed the 3R,2S configuration for the natural minalemines and the R configuration for the constituent beta -amino diacid, Ncma.

  DOI：

  10.1021/jo010076t
• 作为产物：
  描述：

  左旋去甲麻黄碱 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.17h， 生成 (4R,5S)-3-((2'S)-2'-allyl-1'-oxononanoyl)-5-phenyl-4-methyl-2-oxazolidinone
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Minalemine A, a Guanidine Peptide from the Marine Tunicate Didemnum rodriguesi

  摘要：

  The total synthesis of the 3S,2S and 3R,2S diastereomers (1a and 1b) of minalemine A and the identification of the natural compound as the 3R,2S isomer is described. The key step in the synthesis is the preparation of the two enantiomers of the beta -amino diacid 3-(N-carboxymethyl)-aminodecanoic acid (Ncma), which were obtained by stereoselective alkylation with allyl bromide of two nonanoic acid imides bearing chiral oxazolidinones as chiral auxiliaries. Natural minalemine A shows identical (1)H NMR and very similar (13)C NMR spectra compared to the two synthetic diastereomers. Sufficient differences in their chromatographic behavior to allow conclusive identification were not found. However, the corresponding N-2-naphthoyl amides presented quite distinct circular dichroism spectra (CD), and these confirmed the 3R,2S configuration for the natural minalemines and the R configuration for the constituent beta -amino diacid, Ncma.

  DOI：

  10.1021/jo010076t