1-(1,5,3-dithiazepan-3-yl)-2-propanol | 1604783-80-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1,5,3-dithiazepan-3-yl)-2-propanol
• 英文别名: 1-(1,5,3-Dithiazepan-3-yl)propan-2-ol；1-(1,5,3-dithiazepan-3-yl)propan-2-ol
• CAS: 1604783-80-3
• 化学式: C₇H₁₅NOS₂
• 分子量: 193.334
• InChiKey: AITIOXXCFXVEMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  74.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 1,2-乙二硫醇 、 异丙醇胺 以 乙醇 、 水 为溶剂， 反应 0.33h， 以85%的产率得到1-(1,5,3-dithiazepan-3-yl)-2-propanol
  参考文献：
  名称：

  Multicomponent reactions of amino alcohols with CH2O and dithiols in the synthesis of 1,3,5-dithiazepanes and macroheterocycles

  摘要：

  A series of new hydroxyl-substituted 1,3,5-dithiazepanes and N,N'-(2-hydroxyethyl)tetrathiadiazacycloalkanes were synthesized by the multicomponent reactions (MCRs) of amino alcohols with formaldehyde and (alpha,omega-dithiols. The MCR with 1,2-dithiol proceeds via a (1+2+1)-cyclocondensation with selective formation of 1,3,5-dithiazepanes. Stereochemisty of the dithiazepane ring was determined by X-ray diffraction. The reaction with higher alpha,omega-dithiols (1,3-propane-, 1,4-butane-, 1,5-pentane-, 1,6-hexanedithiol and 2-[2-(2-sulfanyletoxy)ethoxy]-1-ethanethiol) yielded OH-substituted macroheterocycles as a result of (2+4+2)-cyclocondensation. The structure of the latter was determined by NMR spectroscopy, MALDI-TOF and electrospray ionization methods. The doubly charged ions like [M+2H](2+) are found in the ESI spectra of the macrocycles. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.053

文献信息

• Multicomponent reactions of amino alcohols with CH2O and dithiols in the synthesis of 1,3,5-dithiazepanes and macroheterocycles
  作者：Guzel R. Khabibullina、Vnira R. Akhmetova、Marat F. Abdullin、Tatiana V. Tyumkina、Leonard M. Khalilov、Askhat G. Ibragimov、Usein M. Dzhemilev

  DOI：10.1016/j.tet.2014.03.053

  日期：2014.5

  A series of new hydroxyl-substituted 1,3,5-dithiazepanes and N,N'-(2-hydroxyethyl)tetrathiadiazacycloalkanes were synthesized by the multicomponent reactions (MCRs) of amino alcohols with formaldehyde and (alpha,omega-dithiols. The MCR with 1,2-dithiol proceeds via a (1+2+1)-cyclocondensation with selective formation of 1,3,5-dithiazepanes. Stereochemisty of the dithiazepane ring was determined by X-ray diffraction. The reaction with higher alpha,omega-dithiols (1,3-propane-, 1,4-butane-, 1,5-pentane-, 1,6-hexanedithiol and 2-[2-(2-sulfanyletoxy)ethoxy]-1-ethanethiol) yielded OH-substituted macroheterocycles as a result of (2+4+2)-cyclocondensation. The structure of the latter was determined by NMR spectroscopy, MALDI-TOF and electrospray ionization methods. The doubly charged ions like [M+2H](2+) are found in the ESI spectra of the macrocycles. (C) 2014 Elsevier Ltd. All rights reserved.