3,3'-bis(1,5,3-dithiazepane) | 1372546-77-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,3'-bis(1,5,3-dithiazepane)
• 英文别名: 3,3'-bi-1,5,3-dithiazepane；bis(1,5,3-dithiazepane-3-yl)；[3,3']bi(1,5,3-dithiazepanyl)；3,3'-Bi-1,5,3-dithiazepane；3-(1,5,3-dithiazepan-3-yl)-1,5,3-dithiazepane
• CAS: 1372546-77-4
• 化学式: C₈H₁₆N₂S₄
• 分子量: 268.492
• InChiKey: GZTUIFBUARODQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,3'-bis(1,5,3-dithiazepane) 、 碘甲烷 以 氯仿 为溶剂， 反应 6.0h， 以88%的产率得到3-(1,5,3-dithiazepan-3-yl)-3-methyl-1,5,3-dithiazepanium iodide
  参考文献：
  名称：

  Novel 1,5,3-dithiazepanes: three-component synthesis, stereochemistry, and fungicidal activity

  摘要：

  氢化肼与甲醛和乙烯-1,2-二硫醇的三组分杂环化反应生成了之前未知的3,3'-双(1,5,3-二噻唑烷)。其立体化学通过X射线衍射确定。与更高的脂肪醛RCHO（R = 甲基、乙基、丙基和丁基）的反应产生了2,4-二烷基-3-烷基亚氨基-1,5,3-二噻唑烷。后者的立体化学通过1H和13C NMR光谱法确定，并通过量子化学计算进行了确认。与乙烯-1,2-二硫醇的苯基氢肼和苄基氢肼的杂环化只在甲醛和乙醛作为醛组分时产生3-氨基-1,5,3-二噻唑烷。3,3'-双(1,5,3-二噻唑烷)及其与甲基碘的N-加成物显示出对微型真菌的杀菌活性。

  DOI：

  10.1007/s11172-012-0301-5
• 作为产物：
  描述：

  聚合甲醛 、 1,2-乙二硫醇 在 一水合肼 作用下， 以 neat (no solvent) 为溶剂， 反应 3.5h， 以81%的产率得到3,3'-bis(1,5,3-dithiazepane)
  参考文献：
  名称：

  Novel 1,5,3-dithiazepanes: three-component synthesis, stereochemistry, and fungicidal activity

  摘要：

  氢化肼与甲醛和乙烯-1,2-二硫醇的三组分杂环化反应生成了之前未知的3,3'-双(1,5,3-二噻唑烷)。其立体化学通过X射线衍射确定。与更高的脂肪醛RCHO（R = 甲基、乙基、丙基和丁基）的反应产生了2,4-二烷基-3-烷基亚氨基-1,5,3-二噻唑烷。后者的立体化学通过1H和13C NMR光谱法确定，并通过量子化学计算进行了确认。与乙烯-1,2-二硫醇的苯基氢肼和苄基氢肼的杂环化只在甲醛和乙醛作为醛组分时产生3-氨基-1,5,3-二噻唑烷。3,3'-双(1,5,3-二噻唑烷)及其与甲基碘的N-加成物显示出对微型真菌的杀菌活性。

  DOI：

  10.1007/s11172-012-0301-5

文献信息

• One-pot synthesis of bis-1,5,3-dithiazepanes and their sorption properties toward silver(I) and palladium(II)
  作者：V. R. Akhmetova、G. R. Anpilogova、G. R. Khabibullina、N. S. Akhmadiev、A. G. Ibragimov

  DOI：10.1134/s1070427214050085

  日期：2014.5
• Hydrazines in the synthesis of 1,5,3-dithiazepane and 1,5,3-dithiazocane derivatives in the presence of catalysts under the action of d- and f-elements
  作者：N. N. Makhmudiyarova、R. Sh. Rakhimov、A. G. Ibragimov、U. M. Dzhemilev

  DOI：10.1134/s1070428014020080

  日期：2014.2

  A method of synthesis was developed for 1,5,3-dithiazepan(dithiazocan)-3-ylamines and 3,3'-bi-1,5,3-dithiazepane(dithiazocane) by hydrazines cyclocondensation with formaldehyde and alpha,omega-alkanedithiols (1,2-ethanedithiol, 1,3-propanedithiol) involving catalysts based on d- and f-elements.
• Novel 1,5,3-dithiazepanes: three-component synthesis, stereochemistry, and fungicidal activity
  作者：V. R. Akhmetova、N. N. Murzakova、T. V. Tyumkina、G. R. Khabibullina、I. S. Bushmarinov、L. F. Korzhova、N. F. Galimzyanova

  DOI：10.1007/s11172-012-0301-5

  日期：2012.11

  Three-component heterocyclization of hydrazine with formaldehyde and ethane-1,2-dithiol gave previously unknown 3,3′-bi(1,5,3-dithiazepane). Its stereochemistry was determined by X-ray diffraction. The reaction with higher aliphatic aldehydes RCHO (R = Me, Et, Prn, and Bun) yielded 2,4-dialkyl-3-alkylideneamino-1,5,3-dithiazepanes. The stereochemistry of the latter was determined by 1H and 13C NMR spectroscopy and confirmed by quantum chemical calculations. Heterocyclizations of phenylhydrazine and benzylhydrazine with ethane-1,2-dithiol gave 3-amino-1,5,3-dithiazepanes only with CH2O and MeCHO as the aldehyde component. 3,3′-Bi(1,5,3-dithiazepane) and its N-adduct with MeI were found to exhibit fungicidal activity against microscopic fungi.

  氢化肼与甲醛和乙烯-1,2-二硫醇的三组分杂环化反应生成了之前未知的3,3'-双(1,5,3-二噻唑烷)。其立体化学通过X射线衍射确定。与更高的脂肪醛RCHO（R = 甲基、乙基、丙基和丁基）的反应产生了2,4-二烷基-3-烷基亚氨基-1,5,3-二噻唑烷。后者的立体化学通过1H和13C NMR光谱法确定，并通过量子化学计算进行了确认。与乙烯-1,2-二硫醇的苯基氢肼和苄基氢肼的杂环化只在甲醛和乙醛作为醛组分时产生3-氨基-1,5,3-二噻唑烷。3,3'-双(1,5,3-二噻唑烷)及其与甲基碘的N-加成物显示出对微型真菌的杀菌活性。
• Efficient synthesis of bis(1,5,3-dithiazepanes). Sorption of palladium(II) from nitric acid solutions
  作者：G. R. Khabibullina、T. M. Buslaeva、E. S. Fedotova、V. R. Akhmetova、A. G. Ibragimov

  DOI：10.1134/s1070363217050127

  日期：2017.5

  Bis(1,5,3-dithiazepanes) have been synthesized via cyclocondensation of aliphatic alpha,omega-diamines and hydrazine with formaldehyde and ethane-1,2-dithiol. Palladium(II) sorption with bis(1,5,3-dithiazepanes) from nitric acid solutions has been studied via a static method. Bis(1,5,3-dithiazepanes) efficiently extract palladium(II) from 0.1-4 mol/L nitric acid solutions at room temperature.