5,11,17,23-tetra-tert-butyl-25-((dimethyl(thiocarbanoyl))oxy)-26,27,28-tris((dimethylcarbamoyl)thio)calix<4>arene | 173344-44-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5,11,17,23-tetra-tert-butyl-25-((dimethyl(thiocarbanoyl))oxy)-26,27,28-tris((dimethylcarbamoyl)thio)calix<4>arene
• 英文别名: O-[[5,11,17,23-tetratert-butyl-26,27,28-tris(dimethylcarbamoylsulfanyl)-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaenyl]] N,N-dimethylcarbamothioate
• CAS: 173344-44-0
• 化学式: C₅₆H₇₆N₄O₄S₄
• 分子量: 997.508
• InChiKey: FCYPEASXQCFUCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.6
• 重原子数：
  68
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  181
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-tert-butyl-25-((dimethyl(thiocarbanoyl))oxy)-26,27,28-tris((dimethylcarbamoyl)thio)calix<4>arene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 p-tert-butylthiacalix[4]arene
  参考文献：
  名称：

  Syntheses and Conformations of the p-tert-Butylcalix[4]arenethiols

  摘要：

  The reaction of dimethyl(thiocarbamoyl) chloride with p-tert-butylcalix[4]arene under various conditions yields mixtures from which most of the conformers of the mono-, bis-, tris-, and tetrakis(dimethyl(thiocarbamoyl))oxy compounds have been isolated and purified. Thermal rearrangement of these compounds produces the (dimethylcarbamoyl)thio compounds which, upon reduction with LiAlH4, afford the tetrathiol 14, the trithiol 16, the 1,3-dithiol 21, and the monothiol24. X-ray crystallographic structure determinations and variable-temperature H-1 NMR studies show that the tetrathiol exists as an immobile 1,3-alternate conformer, the trithiol as a semimobile partial cone/1,3-alternate conformer, the 1,3-dithiol as a mobile flattened cone conformer; and the monothiol as a mobile cone conformer. Although the tetrakis(( dimethylcarbamoyl)thio) compound exists in three noninterconverting forms comprising the 1,2-alternate 13, partial cone 18, and 1,3-alternate 19 conformers, all three yield the same tetrathiol 14 upon reduction. Similarly, the syn 22 and anti 20 conformers of the 1,3-bis((dimethylcarbamoyl)thio) compound yield the same dithiol 21. Molecular mechanics calculations for each of the conformers of the mono-, 1,3-di-, tri-, and tetrathiols show general agreement with the X-ray data.

  DOI：

  10.1021/jo00131a014
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 在 sodium hydride 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 26.0h， 生成 5,11,17,23-tetra-tert-butyl-25-((dimethyl(thiocarbanoyl))oxy)-26,27,28-tris((dimethylcarbamoyl)thio)calix<4>arene
  参考文献：
  名称：

  Syntheses and Conformations of the p-tert-Butylcalix[4]arenethiols

  摘要：

  The reaction of dimethyl(thiocarbamoyl) chloride with p-tert-butylcalix[4]arene under various conditions yields mixtures from which most of the conformers of the mono-, bis-, tris-, and tetrakis(dimethyl(thiocarbamoyl))oxy compounds have been isolated and purified. Thermal rearrangement of these compounds produces the (dimethylcarbamoyl)thio compounds which, upon reduction with LiAlH4, afford the tetrathiol 14, the trithiol 16, the 1,3-dithiol 21, and the monothiol24. X-ray crystallographic structure determinations and variable-temperature H-1 NMR studies show that the tetrathiol exists as an immobile 1,3-alternate conformer, the trithiol as a semimobile partial cone/1,3-alternate conformer, the 1,3-dithiol as a mobile flattened cone conformer; and the monothiol as a mobile cone conformer. Although the tetrakis(( dimethylcarbamoyl)thio) compound exists in three noninterconverting forms comprising the 1,2-alternate 13, partial cone 18, and 1,3-alternate 19 conformers, all three yield the same tetrathiol 14 upon reduction. Similarly, the syn 22 and anti 20 conformers of the 1,3-bis((dimethylcarbamoyl)thio) compound yield the same dithiol 21. Molecular mechanics calculations for each of the conformers of the mono-, 1,3-di-, tri-, and tetrathiols show general agreement with the X-ray data.

  DOI：

  10.1021/jo00131a014

文献信息

• Syntheses and Conformations of the p-tert-Butylcalix[4]arenethiols
  作者：Charles G. Gibbs、P. K. Sujeeth、Janet S. Rogers、George G. Stanley、Mariusz Krawiec、William H. Watson、C. David Gutsche

  DOI：10.1021/jo00131a014

  日期：1995.12

  The reaction of dimethyl(thiocarbamoyl) chloride with p-tert-butylcalix[4]arene under various conditions yields mixtures from which most of the conformers of the mono-, bis-, tris-, and tetrakis(dimethyl(thiocarbamoyl))oxy compounds have been isolated and purified. Thermal rearrangement of these compounds produces the (dimethylcarbamoyl)thio compounds which, upon reduction with LiAlH4, afford the tetrathiol 14, the trithiol 16, the 1,3-dithiol 21, and the monothiol24. X-ray crystallographic structure determinations and variable-temperature H-1 NMR studies show that the tetrathiol exists as an immobile 1,3-alternate conformer, the trithiol as a semimobile partial cone/1,3-alternate conformer, the 1,3-dithiol as a mobile flattened cone conformer; and the monothiol as a mobile cone conformer. Although the tetrakis(( dimethylcarbamoyl)thio) compound exists in three noninterconverting forms comprising the 1,2-alternate 13, partial cone 18, and 1,3-alternate 19 conformers, all three yield the same tetrathiol 14 upon reduction. Similarly, the syn 22 and anti 20 conformers of the 1,3-bis((dimethylcarbamoyl)thio) compound yield the same dithiol 21. Molecular mechanics calculations for each of the conformers of the mono-, 1,3-di-, tri-, and tetrathiols show general agreement with the X-ray data.