1,2,5-trithiepane 5-S-oxide | 22809-86-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: 1,2,5-trithiepane 5-S-oxide
• 英文别名: 1,2,5-Trithiepan-5-oxid；1,2,5-Trithiepane 5-oxide
• CAS: 22809-86-5
• 化学式: C₄H₈OS₃
• 分子量: 168.305
• InChiKey: PIIRICGUEIZSSX-UHFFFAOYSA-N

物化性质

• 熔点：
  95-96 °C
• 沸点：
  390.8±22.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,5-trithiepane 5-S-oxide 以 乙酸酐 为溶剂， 反应 0.58h， 以20%的产率得到3,4-Dihydro-[1,2,5]trithiepine
  参考文献：
  名称：

  1,2,5-Trithiepin:  A 10π-Electron Heteroaromatic System

  摘要：

  The unsubstituted 1,2,5-trithiepin (1) has been synthesized from the known 1,2,5-trithiepane (6) through two consecutive Pummerer rearrangements. Proton and carbon NMR spectra were completely analyzed, assigned, and correlated. The protons in 1 are shifted downfield by Delta delta = 0.57 ppm for H-3/H-7 (delta = 6.57 ppm) and by 1.10 ppm far H-4/H-6 (delta = 7.24 ppm) relative to the 6,7-dihydro-1,2,5-trithiepin (7), These downfield shifts are comparable to thiophene, thus characterizing 1,2,5-trithiepin (1) as the first multisulfur 10 pi-aromatic diatropic molecule incorporating a disulfide linkage. 6,7-Dihydro-1,2,5-trithiepin (7) is a dynamic system. Variable-temperature H-1-NMR measurements of 7 yielded an estimated free energy of activation at the coalescence temperature (227 K) of Delta G(double dagger) = 9.83 kcal/mol.

  DOI：

  10.1021/jo9519625
• 作为产物：
  描述：

  1,2,5-trithiacycloheptane 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以50%的产率得到1,2,5-trithiepane 5-S-oxide
  参考文献：
  名称：

  1,2,5-Trithiepin:  A 10π-Electron Heteroaromatic System

  摘要：

  The unsubstituted 1,2,5-trithiepin (1) has been synthesized from the known 1,2,5-trithiepane (6) through two consecutive Pummerer rearrangements. Proton and carbon NMR spectra were completely analyzed, assigned, and correlated. The protons in 1 are shifted downfield by Delta delta = 0.57 ppm for H-3/H-7 (delta = 6.57 ppm) and by 1.10 ppm far H-4/H-6 (delta = 7.24 ppm) relative to the 6,7-dihydro-1,2,5-trithiepin (7), These downfield shifts are comparable to thiophene, thus characterizing 1,2,5-trithiepin (1) as the first multisulfur 10 pi-aromatic diatropic molecule incorporating a disulfide linkage. 6,7-Dihydro-1,2,5-trithiepin (7) is a dynamic system. Variable-temperature H-1-NMR measurements of 7 yielded an estimated free energy of activation at the coalescence temperature (227 K) of Delta G(double dagger) = 9.83 kcal/mol.

  DOI：

  10.1021/jo9519625

文献信息

• 1,2,5-Trithiepin:  A 10π-Electron Heteroaromatic System
  作者：Shou-Nan Ueng、Michael Blumenstein、Klaus G. Grohmann

  DOI：10.1021/jo9519625

  日期：1997.4.1

  The unsubstituted 1,2,5-trithiepin (1) has been synthesized from the known 1,2,5-trithiepane (6) through two consecutive Pummerer rearrangements. Proton and carbon NMR spectra were completely analyzed, assigned, and correlated. The protons in 1 are shifted downfield by Delta delta = 0.57 ppm for H-3/H-7 (delta = 6.57 ppm) and by 1.10 ppm far H-4/H-6 (delta = 7.24 ppm) relative to the 6,7-dihydro-1,2,5-trithiepin (7), These downfield shifts are comparable to thiophene, thus characterizing 1,2,5-trithiepin (1) as the first multisulfur 10 pi-aromatic diatropic molecule incorporating a disulfide linkage. 6,7-Dihydro-1,2,5-trithiepin (7) is a dynamic system. Variable-temperature H-1-NMR measurements of 7 yielded an estimated free energy of activation at the coalescence temperature (227 K) of Delta G(double dagger) = 9.83 kcal/mol.