3,7-bis(butylmethylamino)-1,5,2,4,6,8-dithiatetrazocine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环化合物
• 英文名称: 3,7-bis(butylmethylamino)-1,5,2,4,6,8-dithiatetrazocine
• 化学式: C₁₂H₂₄N₆S₂
• 分子量: 316.495
• InChiKey: AWTFAEZTOWMXSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  55.92
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  甲基丁胺 在 二氯化硫 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 3,7-bis(butylmethylamino)-1,5,2,4,6,8-dithiatetrazocine
  参考文献：
  名称：

  Conformational Dynamics of the Bent 1,5,2,4,6,8-Dithiatetrazocines

  摘要：

  3,7-Bis(butylmethylamino)-1,5,2,4,6,8-dithiatetrazocine (3) was prepared in two steps from N-methylbutylamine in 14% overall yield. At room temperature the H-1 NMR spectrum of 3 shows two methyl resonances (in a roughly 1:1 ratio) and four resonances for the C-alpha methylene protons of the butyl groups (roughly 1:1:1:1). These data indicate that compound 3 displays both cis/trans isomerism and a bent heterocyclic ring in solution. Heating of compound 3 in a variable-temperature NMR experiment results in coalescence of the two methyl and four C-alpha resonances to a singlet and a triplet, respectively, at temperatures corresponding to an activation energy (Delta G(c)(double dagger)) of a of approximately 17 kcal/mol for the exchange process. This value is the free energy of activation for rotation of the dialkylamino groups and also represents a lower limit for the activation energy for inversion of the bent dithiatetrazocine ring. Ab initio calculations on the 3,7-diamino-1,5,2,4,6,8-dithiatetrazocine system suggest that the activation energies for amine rotation and ring inversion are very similar: 17.1 and 17.3 kcal/mol, respectively. Spectral simulations of the NMR data for 3 support this conclusion, with the best experimental estimates of the free energies of activation for the two processes being 17.3 +/- 0.1 and 17.7 +/- 0.5 kcal/mol, respectively. Notably, the calculations indicate that the ring inversion precedes asymmetrically-in the transition state one side of the ring is more highly bent than the other-and there is a nearly planar intermediate along the pathway.

  DOI：

  10.1021/ja00091a021