(2S)-2-[[(1R)-2-hydroxy-1-phenylethyl]amino]-2-(3-methoxy-5-propan-2-yloxyphenyl)acetonitrile | 168292-16-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S)-2-[[(1R)-2-hydroxy-1-phenylethyl]amino]-2-(3-methoxy-5-propan-2-yloxyphenyl)acetonitrile
• CAS: 168292-16-8
• 化学式: C₂₀H₂₄N₂O₃
• 分子量: 340.422
• InChiKey: VGFGFXTZFXMQAS-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-[[(1R)-2-hydroxy-1-phenylethyl]amino]-2-(3-methoxy-5-propan-2-yloxyphenyl)acetonitrile 在 lead(IV) acetate 、 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.17h， 生成 methyl (2S)-2-amino-2-(3-methoxy-5-propan-2-yloxyphenyl)acetate
  参考文献：
  名称：

  A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction

  摘要：

  An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides. The nonproteinogenic alpha-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary. The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.

  DOI：

  10.1021/jo00125a026
• 作为产物：
  描述：

  3,5-二羟基苯甲酸甲酯 在 lithium aluminium tetrahydride 、 四乙基碘化铵 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 28.5h， 生成 (2S)-2-[[(1R)-2-hydroxy-1-phenylethyl]amino]-2-(3-methoxy-5-propan-2-yloxyphenyl)acetonitrile
  参考文献：
  名称：

  A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction

  摘要：

  An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides. The nonproteinogenic alpha-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary. The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.

  DOI：

  10.1021/jo00125a026

文献信息

• A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction
  作者：Jieping Zhu、Rene Beugelmans、Sebastien Bourdet、Jacqueline Chastanet、George Roussi

  DOI：10.1021/jo00125a026

  日期：1995.10

  An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1. Chloride as well as fluoride could be used as the leaving group in this reaction. However, the latter was preferred since it required milder conditions. Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides. The nonproteinogenic alpha-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary. The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.