N-((1R,2R)-2-Thioacetylamino-cyclohexyl)-thioacetamide

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代酰胺
• 英文名称: N-((1R,2R)-2-Thioacetylamino-cyclohexyl)-thioacetamide
• 英文别名: Boxpiepbgmxdqq-nxezzachsa-；N-[(1R,2R)-2-(ethanethioylamino)cyclohexyl]ethanethioamide
• 化学式: C₁₀H₁₈N₂S₂
• 分子量: 230.398
• InChiKey: BOXPIEPBGMXDQQ-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  88.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,2R)-1,2-diaminocyclohexane 在 2,4-bis<4-(methylthio)phenyl>-1,3,2,4-dithiadiphosphetane 2,4-disulfide 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 25.0h， 生成 N-((1R,2R)-2-Thioacetylamino-cyclohexyl)-thioacetamide
  参考文献：
  名称：

  Stereochemical Studies of 1,2-Di(thio)acetamidocyclohexanes and their N,N'-Dimethyl Derivatives by NMR and CD Spectroscopy and by Molecular Mechanics Calculations.

  摘要：

  The configurations and conformations of cis- and trans- 1,2-di (thio) acetamidocyclohexane and their N,N'-dimethyl derivatives have been studied by H-1 and C-13 NMR spectroscopy, using chemical shifts and coupling constants, difference NOE H-1 NMR spectra and 2D H-1-C-13 NMR correlation spectra. For the trans compounds, the Z,Z configuration of the (thio)amide groups with equatorial (thio)acetamido groups was found to be strongly preferred. For the cis compounds, E,Z configurations of the (thio)amide groups with axial E and equatorial Z groups were found to be preferred. Empirical force-field calculations with the MM2(91) force field led to predictions for the most stable configurations and conformations, mostly in very good agreement with those obtained by NMR spectroscopy.CD spectra recorded for the trans-(R,R)-N-methyl compounds in acetonitrile solution agreed well with those calculated on the basis of geometries from force-field calculations. The CD spectra calculated for the trans-(R,R)-NH- compounds and for the cis-monothio compounds showed poor agreement with the experimental spectra.

  DOI：

  10.3891/acta.chem.scand.50-0938

文献信息

• Stereochemical Studies of 1,2-Di(thio)acetamidocyclohexanes and their N,N'-Dimethyl Derivatives by NMR and CD Spectroscopy and by Molecular Mechanics Calculations.
  作者：Agha Zul-Qarnain Khan、Galya I. Ivanova、Stefan L. Spassov、Jan Sandström、Pál Sohár、Reijo Sillanpää、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0938

  日期：——

  The configurations and conformations of cis- and trans- 1,2-di (thio) acetamidocyclohexane and their N,N'-dimethyl derivatives have been studied by H-1 and C-13 NMR spectroscopy, using chemical shifts and coupling constants, difference NOE H-1 NMR spectra and 2D H-1-C-13 NMR correlation spectra. For the trans compounds, the Z,Z configuration of the (thio)amide groups with equatorial (thio)acetamido groups was found to be strongly preferred. For the cis compounds, E,Z configurations of the (thio)amide groups with axial E and equatorial Z groups were found to be preferred. Empirical force-field calculations with the MM2(91) force field led to predictions for the most stable configurations and conformations, mostly in very good agreement with those obtained by NMR spectroscopy.CD spectra recorded for the trans-(R,R)-N-methyl compounds in acetonitrile solution agreed well with those calculated on the basis of geometries from force-field calculations. The CD spectra calculated for the trans-(R,R)-NH- compounds and for the cis-monothio compounds showed poor agreement with the experimental spectra.

表征谱图