(1R,2R)-1-benzylthio-2-[N-(3,5-dinitrobenzoyl)amino] cyclohexane | 1415424-76-8

• 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: (1R,2R)-1-benzylthio-2-[N-(3,5-dinitrobenzoyl)amino] cyclohexane
• 英文别名: N-(2-(benzylthio)cyclohexyl)-3,5-dinitrobenzamide；N-[(1R,2R)-2-benzylsulfanylcyclohexyl]-3,5-dinitrobenzamide
• CAS: 1415424-76-8
• 化学式: C₂₀H₂₁N₃O₅S
• 分子量: 415.47
• InChiKey: OTHNVYXABVBKSD-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]heptane 、 苄硫醇 在 苯膦酸 作用下， 生成 (1R,2R)-1-benzylthio-2-[N-(3,5-dinitrobenzoyl)amino] cyclohexane
  参考文献：
  名称：

  Chiral Phosphoric Acid-Catalyzed Desymmetrization of meso-Aziridines with Functionalized Mercaptans

  摘要：

  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.

  DOI：

  10.1021/ol902123h

文献信息

• Studies on the true catalyst in the phosphate-promoted desymmetrization of meso-aziridines with silylated nucleophiles
  作者：Giorgio Della Sala

  DOI：10.1016/j.tet.2012.10.068

  日期：2013.1

  Significant amounts of metal phosphate impurities have been detected by NMR spectroscopy and ICP-OES analysis of synthetic, as well as purchased, samples of VAPOL hydrogen phosphate purified on silica gel. The previously reported VAPOL hydrogen phosphate-catalyzed desymmetrization of meso-aziridines with different silylated compounds, has been re-examined. While metal-free phosphoric acid exhibited low activity and enantioselectivity, calcium and magnesium phosphate salts proved to be the true catalysts in these related processes. Reproducible high enantioselectivities were obtained in the ring-opening of cyclic meso-aziridines with Me3SiX (X=SPh, SePh, N-3) employing a 1:1 mixture of calcium and magnesium VAPOL phosphates. The reaction has been successfully extended to Me3SiSBn, Me3SiSMe and Me3SiNCS, giving ring-opened products in high yield and unprecedented moderate to good enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.