2-[14-(2-hydroxyethyl)-1,5,12,16-tetrathia-3,14-diazacyclodocos-3-yl]-ethanol | 1604783-99-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: 2-[14-(2-hydroxyethyl)-1,5,12,16-tetrathia-3,14-diazacyclodocos-3-yl]-ethanol
• 英文别名: 2-[14-(2-hydroxyethyl)-1,5,12,16-tetrathia-3,14-diazacyclodocosan-3-yl]-1-ethanol
• CAS: 1604783-99-4
• 化学式: C₂₀H₄₂N₂O₂S₄
• 分子量: 470.83
• InChiKey: XXEWBZKOEOGURD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.94
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-[14-(2-hydroxyethyl)-1,5,12,16-tetrathia-3,14-diazacyclodocos-3-yl]-ethanol 以 乙醇 、 水 为溶剂， 反应 0.33h， 以12%的产率得到1,12-dioxa-3,10,14,21-tetrathiacyclodocosane
  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
• 作为产物：
  描述：

  1,12-dioxa-3,10,14,21-tetrathiacyclodocosane 、 C.I.酸性橙108 以 氯仿 为溶剂， 生成 2-[14-(2-hydroxyethyl)-1,5,12,16-tetrathia-3,14-diazacyclodocos-3-yl]-ethanol
  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

• One-pot synthesis and fungicidal activity of 2-(1,5,3-dithiazepan-3-yl)ethanol and N,N′-bis(2-hydroxyethyl)tetrathiadiazacycloalkanes
  作者：V. R. Akhmetova、G. R. Khabibullina、N. F. Galimzyanova、A. G. Ibragimov

  DOI：10.1134/s1070427214030082

  日期：2014.3

  Synthesis of 2-(1,5,3-dithiazepan-3-yl)ethanol and N,N'-bis(2-hydroxyethyl)tetrathiadiazacycloalkanes was performed by multicomponent condensation of monoethanolamine with formaldehyde and SH-acids (1,2-ethane, 1,3-propane-, 1,4-butane-, 1,5-pentane-, and 1,6-hexanedithiols). The resulting S,N-containing heterocycles and macrocycles possess fungicidal properties relative to microscopic fungi, plant pathogens.