10-(4-Methylphenylsulfonyl)-1,7-dioxa-4-thia-10-azacyclododecane | 146945-09-7

• 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: 10-(4-Methylphenylsulfonyl)-1,7-dioxa-4-thia-10-azacyclododecane
• 英文别名: 10-(4-methylphenyl)sulfonyl-1,7-dioxa-4-thia-10-azacyclododecane
• CAS: 146945-09-7
• 化学式: C₁₅H₂₃NO₄S₂
• 分子量: 345.484
• InChiKey: AEKYZEZGTBAREX-UHFFFAOYSA-N

物化性质

• 沸点：
  518.9±60.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  10-(4-Methylphenylsulfonyl)-1,7-dioxa-4-thia-10-azacyclododecane 在 sodium anthracenide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.08h， 以19%的产率得到1,7-Dioxa-4-thia-10-azacyclododecane
  参考文献：
  名称：

  Synthesis, characterization and crystal structures of 1,7-dioxa-4-thia-10-azacyclododecane ([12]aneNO2S) and [Hg([12]aneNO2S)(NO3)2]

  摘要：

  Reaction of 6-(4-methylphenylsulfonyl)-1,11-bis(4-methylphenylsulfonyloxy)-3,9-dioxa-6-azaundecane and ethane-1,2-dithiol in the presence of NaH, results, after removal of the protecting group, in the unexpected isolation of the twelve-membered macrocycle 1,7-dioxa-4-thia-10-azacyclododecane, [12]aneNO2S. The product, suggested to arise from the intramolecular displacement of a tosyl group by a thioether instead of the terminal thiol as in the expected ring closing procedure, was characterised by C-13 NMR spectroscopy, mass spectrometry, microanalysis and a single-crystal X-ray structure determination. The macrocycle crystallizes in the monoclinic space group P2(1), with a = 7.448(5), b = 5.1740(10), c = 12.769(9) angstrom, beta = 93.28(2)-degrees, Z = 2 with R = 0.046. All the donors in the macrocyclic ring are in the endodentate conformation with close contacts between the N-H and atoms 0(1) and 0(7). Reaction of mercury nitrate with 1 molar equivalent of [12]aneNO2S in methanol, and subsequent crystallization of the product, resulted in colourless prisms of [Hg([12]aneNO2S)(NO3)2] which crystallize in the monoclinic space group P2(1)/c, with a = 9.165(17), b = 10.657(15), c = 14.80(2) angstrom, beta = 92.57(8)-degrees, Z = 4 with R = 0.055. In this molecule the mercury(II) cation is co-ordinated by the macrocyclic donors and the nitrate anions, one in a bidentate manner, the other in a monodentate mode.

  DOI：

  10.1039/dt9930000625
• 作为产物：
  描述：

  1,11-bis(4-tolylsulphonyloxy)-6-(4-tolylsulphonyl)-3,9-dioxa-6-azaundecane 在 1,2-Ethanedithiol, disodium salt 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以75%的产率得到10-(4-Methylphenylsulfonyl)-1,7-dioxa-4-thia-10-azacyclododecane
  参考文献：
  名称：

  Synthesis, characterization and crystal structures of 1,7-dioxa-4-thia-10-azacyclododecane ([12]aneNO2S) and [Hg([12]aneNO2S)(NO3)2]

  摘要：

  Reaction of 6-(4-methylphenylsulfonyl)-1,11-bis(4-methylphenylsulfonyloxy)-3,9-dioxa-6-azaundecane and ethane-1,2-dithiol in the presence of NaH, results, after removal of the protecting group, in the unexpected isolation of the twelve-membered macrocycle 1,7-dioxa-4-thia-10-azacyclododecane, [12]aneNO2S. The product, suggested to arise from the intramolecular displacement of a tosyl group by a thioether instead of the terminal thiol as in the expected ring closing procedure, was characterised by C-13 NMR spectroscopy, mass spectrometry, microanalysis and a single-crystal X-ray structure determination. The macrocycle crystallizes in the monoclinic space group P2(1), with a = 7.448(5), b = 5.1740(10), c = 12.769(9) angstrom, beta = 93.28(2)-degrees, Z = 2 with R = 0.046. All the donors in the macrocyclic ring are in the endodentate conformation with close contacts between the N-H and atoms 0(1) and 0(7). Reaction of mercury nitrate with 1 molar equivalent of [12]aneNO2S in methanol, and subsequent crystallization of the product, resulted in colourless prisms of [Hg([12]aneNO2S)(NO3)2] which crystallize in the monoclinic space group P2(1)/c, with a = 9.165(17), b = 10.657(15), c = 14.80(2) angstrom, beta = 92.57(8)-degrees, Z = 4 with R = 0.055. In this molecule the mercury(II) cation is co-ordinated by the macrocyclic donors and the nitrate anions, one in a bidentate manner, the other in a monodentate mode.

  DOI：

  10.1039/dt9930000625