2-phenylthio-3-[N-(3,5-dinitrobenzoyl)amino]butane

• 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: 2-phenylthio-3-[N-(3,5-dinitrobenzoyl)amino]butane
• 英文别名: 3,5-dinitro-N-(3-(phenylthio)butan-2-yl)benzamide；3,5-dinitro-N-[(2R,3R)-3-phenylsulfanylbutan-2-yl]benzamide
• 化学式: C₁₇H₁₇N₃O₅S
• 分子量: 375.405
• InChiKey: NQSHGCRYSRGVLZ-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  146
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  cis-1-(3,5-dinitrobenzoyl)-2,3-dimethylaziridine 、 苯基硫三甲基硅烷 在 (R)-VAPOL 作用下， 以 三氯乙烷 为溶剂， 反应 6.0h， 以88%的产率得到2-phenylthio-3-[N-(3,5-dinitrobenzoyl)amino]butane
  参考文献：
  名称：

  Highly Enantioselective Synthesis of β-Amidophenylthioethers by Organocatalytic Desymmetrization of meso-Aziridines

  摘要：

  The desymmetrization of N-acylaziridines with Me3SiSPh, catalyzed by commercially available (R) and (S)-VAPOL hydrogen phosphate, produced beta-(N-acylamino)phenylthioethers in a highly enantioselective and efficient manner (78-99% ee). The selection of the suitable aziridine/nucleophile/catalyst molar ratio is crucial to obtain high ee's.

  DOI：

  10.1021/ol901209n

文献信息

• Chiral Phosphoric Acid-Catalyzed Desymmetrization of <i>meso</i>-Aziridines with Functionalized Mercaptans
  作者：Shawn E. Larson、Juan C. Baso、Guilong Li、Jon C. Antilla

  DOI：10.1021/ol902123h

  日期：2009.11.19

  Conditions for the phosphoric acid-catalyzed highly enantioselective ring-opening of meso-aziridines with a series of functionalized aromatic thiol nucleophiles are described. The procedure utilizes commercially available aromatic thiols, a series of meso-aziridines, and a catalytic amount of VAPOL phosphoric acid to explore the substrate scope of this highly enantioselective reaction.
• Highly Enantioselective Synthesis of β-Amidophenylthioethers by Organocatalytic Desymmetrization of <i>meso</i>-Aziridines
  作者：Giorgio Della Sala、Alessandra Lattanzi

  DOI：10.1021/ol901209n

  日期：2009.8.6

  The desymmetrization of N-acylaziridines with Me3SiSPh, catalyzed by commercially available (R) and (S)-VAPOL hydrogen phosphate, produced beta-(N-acylamino)phenylthioethers in a highly enantioselective and efficient manner (78-99% ee). The selection of the suitable aziridine/nucleophile/catalyst molar ratio is crucial to obtain high ee's.