5-(tert-butyl)-1,3,5-triazinane-2-thione | 2669-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪烷类
• 英文名称: 5-(tert-butyl)-1,3,5-triazinane-2-thione
• 英文别名: 5-Tert-butyl-1,3,5-triazinane-2-thione
• CAS: 2669-96-7
• 化学式: C₇H₁₅N₃S
• mdl: MFCD00023165
• 分子量: 173.282
• InChiKey: KFHMIFDHPDEVCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  59.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(tert-butyl)-1,3,5-triazinane-2-thione 、 4-氨基丁酸 以 水 为溶剂， 反应 48.0h， 以65.1%的产率得到4-(4-硫代-1,3,5-三嗪-1-基)丁酸
  参考文献：
  名称：

  Alkylation of cyclic mannich bases, derivatives of thiourea and simple amino acids

  摘要：

  Aminomethylation of thiourea with aqueous formaldehyde and simple amino acids (glycine, beta-alanine, gamma-aminobutyric acid) have resulted in the formation of (4-thioxo-1,3,5-triazinan-1-yl)-substituted acetic, propionic, and butyric acids, respectively. By alkylation of these compounds corresponding S-methyl and S-ethyl iodides were obtained, and by the action of tert-butylamine, the corresponding salts. The same salts were obtained by the reaction of amine exchange between 5-tert-butyl-1,3,5-triazinan-2-thione and these amino acids in water. As a result of neutralization of S-methyl iodides with tert-butylamine in 2-propanol or aqueous 2-propanol zwitterionic [4-(methyl-sulfanyl)-3,6-dihydro-1,3,5-triazin-1(2H)-yl] derivatives of these acids were isolated. From aqueous solutions of S-methyl iodides and tert-butylamine ion associates of the corresponding zwitter-ions and tert-butylammonium iodide have crystallized. The same associates have formed at treating S-methyl iodides with tert-butylamine or diethylamine in the absence of a solvent.

  DOI：

  10.1134/s1070363212020132
• 作为产物：
  描述：

  5-tert-butyl-1-hydroxymethylhexahydro-1,3,5-triazine-2-thione 在 sodium disulfite 作用下， 以 水 为溶剂， 反应 0.08h， 以48%的产率得到5-(tert-butyl)-1,3,5-triazinane-2-thione
  参考文献：
  名称：

  Lazarev; Ramsh; Ivanenko, Russian Journal of General Chemistry, 2000, vol. 70, # 3, p. 442 - 449

  摘要：

  DOI：

文献信息

• Straightforward Three-Component Synthesis of N′,N′′-Disubstituted N-Alkyl-1,3,5-Triazinanes
  作者：Alexey V. Kletskov、Antonio Frontera、Anna A. Sinelshchikova、Mikhail S. Grigoriev、Vladimir P. Zaytsev、Mariya V. Grudova、Alexander S. Bunev、Sofia Presnukhina、Anton Shetnev、Fedor I. Zubkov

  DOI：10.1055/s-0039-1690900

  日期：2020.7

  Efficient approaches towards the synthesis of various N-substituted 1,3,5-triazinanes based on a transformation of N-alkyl-1,5,3-dioxazepanes or on a domino reaction involving condensation of various amines, amides, and paraformaldehyde are described for the first time. Mg(ClO4)2 was shown to be one of the most potent additives for the condensation. The proposed approaches permit the synthesis of a

  描述了基于 N-烷基-1,5,3-二氧杂环戊烷的转化或涉及各种胺、酰胺和多聚甲醛缩合的多米诺反应合成各种 N-取代的 1,3,5-三嗪烷的有效方法首次。Mg(ClO4)2 被证明是最有效的缩合添加剂之一。所提出的方法允许以相对容易的后处理以良好的产率合成广谱的取代的对称三嗪烷。在多组分反应的情况下，该方法允许从简单易得的试剂制备目标物质。在体外生物测定中发现所得化合物的代表不具有抗微生物或细胞毒性活性。
• Catalytic cycloaminomethylation of ureas and thioureas with N,N-bis(methoxymethyl)alkanamines
  作者：R. R. Khairullina、A. R. Geniyatova、E. S. Meshcheryakova、L. M. Khalilov、A. G. Ibragimov、U. M. Dzhemilev

  DOI：10.1134/s1070428015010200

  日期：2015.1

  An efficient procedure has been developed for the synthesis of 5-alkyl-1,3,5-triazinan-2-ones, 5-alkyl-1,3,5-triazinane-2-thiones, and 2,6-dialkylhexahydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8(1H,5H)-diones by reactions of urea, thiourea, and tetrahydroimidazo[4,5-d]imidazole-2,5-(1H,3H)-dione with N,N-bis(methoxymethyl)alkanamines in the presence of SmCl3 · 6 H2O as catalyst.

  已经开发出一种有效的程序，用于合成5-烷基-1,3,5-三嗪二-2-酮，5-烷基-1,3,5-三嗪烷-2-硫酮和2,6-二烷基六氢-2 ，3a，4a，6,7a，8a-六氮杂环戊[ def ]芴-4,8 （1 H，5 H）-二酮通过脲，硫脲和四氢咪唑[4,5 - d ]咪唑-2,5的反应在SmCl 3 ·6 H 2 O作为催化剂的情况下，用N，N-双（甲氧基甲基）烷胺与-（1 H，3 H）-二酮。
• Synthesis of 5-alkyl-1,3,5-triazinan-2-ones and 5-alkyl-1,3,5-triazinane-2-thiones using Cu- and Sm-containing catalysts
  作者：R. R. Khairullina、A. R. Geniyatova、A. G. Ibragimov、U. M. Dzhemilev

  DOI：10.1134/s1070428013060171

  日期：2013.6

  Efficient procedures have been developed for the synthesis of 5-alkyl-1,3,5-triazinan-2-ones and 5-alkyl-1,3,5-triazinane-2-thiones by reaction of urea (thiourea) with primary alkylamines and N,N,N',N'-tetramethylmethylenediamine and by reaction of primary amines with N,N'-bis(dimethylaminomethyl)urea(thiourea) in the presence of Cu- and Sm-containing catalysts.
• Amine exchange reactions of 3-tert-butyl-6-(methylsulfanyl)-1,2,3,4-tetrahydro-1,3,5-triazine hydroiodide with amino acids
  作者：Sun Min’yan’、S. M. Ramsh、V. S. Fundamenskii、S. Yu. Solov’eva、V. I. Zakharov

  DOI：10.1134/s1070363210030242

  日期：2010.3

  3-tert-Butyl-6-(methylsulfanyl)-1,2,3,4-tetrahydro-1,3,5-triazine hydroiodide enters into the amine exchange reaction with glycine and beta-alanine in aqueous solution. The final exchange products are [4-(methylsulfanyl)-5,6-dihydro-1,3,5-triazin-3-ium-1(2H)-yl] acetate and 3-[4-(methylsulfanyl)-5, 6-dihydro-1,3,5-triazin-3-ium-1(2H)-yl] propanoate, respectively, crystallizing together with t-butylamine hydroiodide from aqueous or aqueous alcoholic solutions as ion associates, which also can be detected in solution in DMSO-d (6). [4-(Methylsulfanyl)-5,6-dihydro-1,3,5-triazin-3-ium-1(2H)-yl] acetate can be extracted directly from the reaction mixture after carrying out the amine exchange in aqueous isopropanol or 95% ethanol, as well as by "recrystallization" of its associate with tert-butylamine hydroiodide from aqueous isopropanol.
• Cyclic thioureas as cumene oxidation inhibitors
  作者：E. N. Garibov、I. A. Rzaeva、N. G. Shykhaliev、A. I. Kuliev、V. M. Farzaliev、M. A. Allakhverdiev

  DOI：10.1134/s1070427210040245

  日期：2010.4

  Hexahydro-1,3,5-triazine-4-thiones were synthesized by ternary condensation of thiourea with various aldehydes and amines. The products were characterized by IR and NMR spectroscopy, and their inhibiting effect on cumene oxidation was examined.