N,N'-diacetyl-trans-1,2-diaminocyclohexane | 54009-70-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-diacetyl-trans-1,2-diaminocyclohexane
• 英文别名: (+/-)-trans-1,2-diacetamidocyclohexane；(+/-)-trans-1.2-bis-acetylamino-cyclohexane；(+/-)-trans-1.2-Bis-acetamino-cyclohexan；N-[(1S,2S)-2-acetamidocyclohexyl]acetamide
• CAS: 54009-70-0；70924-77-5；70924-78-6
• 化学式: C₁₀H₁₈N₂O₂
• 分子量: 198.265
• InChiKey: MZYLAHHTXWRMOL-UWVGGRQHSA-N

物化性质

• 熔点：
  272 °C
• 沸点：
  469.1±25.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 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：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N,N'-diacetyl-trans-1,2-diaminocyclohexane 在 2,4-bis<4-(methylthio)phenyl>-1,3,2,4-dithiadiphosphetane 2,4-disulfide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以100%的产率得到
  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
• 作为产物：
  描述：

  乙酸酐 、 trans-1,2-Diaminocyclohexane 以 氯仿 为溶剂， 反应 1.0h， 以100%的产率得到N,N'-diacetyl-trans-1,2-diaminocyclohexane
  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

• Synthesis, crystal structure, IR and Raman properties of 1,2-diacetamidocyclohexane and its complexes with ZnBr2 and HBr3
  作者：A. Bekaert、P. Lemoine、B. Viossat、M. Jouan、P. Gemeiner、J.D. Brion

  DOI：10.1016/j.molstruc.2004.10.068

  日期：2005.3

  X-ray crystallography, infrared absorption and Raman scattering were applied to study the influence of Zn(II) or H+ on the amidic bond. (R,R)-1,2-diacetamidocyclohexane (DAACH) was chosen as a conformationally strained chiral building block including two amide bonds; this model is hoped to be not too far from a peptide and gives easily crystalline complexes. Crystallographic structures of DAACH molecule

  应用 X 射线晶体学、红外吸收和拉曼散射来研究 Zn(II) 或 H+ 对酰胺键的影响。(R,R)-1,2-二乙酰氨基环己烷 (DAACH) 被选为包含两个酰胺键的构象应变手性结构单元；希望这个模型离肽不太远，并且容易产生结晶复合物。研究了 DAACH 分子 (1)、DAACH/ZnBr2 (2) 和 DAACH/HBr3 (3) 复合物的晶体结构。DAACH 络合 Zn 是由于酰胺键的超极化。1-3 的 IR 和拉曼研究与 X 射线结果一致。这可能是研究金属/蛋白质相互作用或多肽酸性变性的模型
• Bifunctional chiral auxiliaries 5: The synthesis of 1,3-diacylimidazolidine-2-thiones and 1,3-diacylimidazolidin-2-ones from 1,2-diamines
  作者：Stephen G. Davies、Andrew A. Mortlock

  DOI：10.1016/s0040-4020(01)85757-4

  日期：1993.1

  Although 1,2-diamines fail to cyclise with urea, phosgene or 1,1'-carbonyl diimidazole, they react with carbon disulphide to give the corresponding imidazolidine-2-thiones. These undergo clean diacylation to give 1,3-diacylimidazolidine-2-thiones which are readily converted to 1,3-diacylimidazolidin-2-ones on treatment with mercury (II) acetate. An alternative two-step route to 1,3-diacylimidazolidin-2-ones uses carbonyl sulphide to effect cyclisation of the 1,2-diamine to the imidazolidin-2-one, which is subsequently diacylated. The ability to convert homochiral 1,2-diamines to homochiral 1,3-diacylimidazolidin-2-ones has also been demonstrated.
• 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