bis(5,5-dimethyl-3-thioxocyclohex-1-en-1-yl) sulfide | 267899-74-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代羰基化合物
• 英文名称: bis(5,5-dimethyl-3-thioxocyclohex-1-en-1-yl) sulfide
• 英文别名: Bis(5,5-dimethyl-3-thioxo-1-cyclohexenyl) sulfide；bis(5,5-dimethyl-3-thioxo-1-cyclohexenyl)sulfide；bis(5,5-dimethyl-3-thioxocyclohex-1-enyl)sulfide；3-(5,5-dimethyl-3-sulfanylidenecyclohexen-1-yl)sulfanyl-5,5-dimethylcyclohex-2-ene-1-thione
• CAS: 267899-74-1
• 化学式: C₁₆H₂₂S₃
• 分子量: 310.549
• InChiKey: JUSMCWYXVVVWLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(5,5-dimethyl-3-thioxocyclohex-1-en-1-yl) sulfide 在 肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以78%的产率得到bis(5,5-dimethyl-3-hydrazonocyclohex-1-enyl)sulfide
  参考文献：
  名称：

  1,7-dithioxo-substituted systems. Synthesis, structure, and photoconductivity of bis(5,5-dimethyl-3-hydrazonocyclohex-1-enyl) sulfide

  摘要：

  Bis(5,5-dimethyl-3-hydrazonocyclohex-1-enyl) sulfide was synthesized by the reaction of bis(5,5-dimethyl-3-thioxocyclohex-1-enyl) sulfide or its oxygen analog with hydrazine. Conformational lability of the molecule of dihydrazone was studied by the DFT(B3LYP) method using expanded basis sets 6-311G and 6-11G(d,p). Analysis of vibration IR and Raman spectra of the most stable conformers of the isolated molecule of dihydrazone was performed at the harmonic approximation. Using the Onsager SCRF solvation model the absence of solvent effect on the relative stability of the conformers was shown. The photoconductivity of dihydrazone was studied. Low value of the ratio of photocurrent to dark current (J (p)/J (d) = 2.5-3.5) for dyhydrazone was assigned to the lability of its stereoelectronic structure, which was in line with the data of (1)H, (13)C, and (15)N NMR spectra.

  DOI：

  10.1134/s1070363210020179
• 作为产物：
  描述：

  3-chloro-5,5-dimethyl-2-cyclohexene-1-thione 在 sodium thiosulfate 作用下， 以 甲醇 为溶剂， 生成 bis(5,5-dimethyl-3-thioxocyclohex-1-en-1-yl) sulfide
  参考文献：
  名称：

  摘要：

  Synthetic routes to bis(5,5-dimethyl-3-thioxo-1-cyclohexenyl) sulfide have been studied. The title compound can be obtained by reaction of 3-chloro-5,5-dimethyl-2-cyclohexenethione with sodium thiosulfate and by condensation of 3-mercapto-5,5-dimethyl-2-cyclohexenethione. The reaction of bis(5,5-dimethyl-3-oxo-1-cyclohexenyl) sulfide with hydrogen sulfide and hydrogen chloride yields 3-oxo-3'-thioxobis(5,5-dimethyl-1-cyclohexenyl) sulfide.

  DOI：

  10.1023/a:1013837026547

文献信息

• 1,7-dithioxo systems. Reaction of 3-[(5,5-dimethyl-3-thioxocyclohex-1-en-1yl)sulfanyl]-5,5-dimethylcyclohex-2-ene-1-thione with 2-aminoethanol and ethane-1,2-diamine
  作者：L. V. Timokhina、L. V. Kanitskaya

  DOI：10.1134/s1070428009120082

  日期：2009.12

  The reaction of 3-[(5,5-dimethyl-3-thioxocyclohex-1-en-1-yl)sulfanyl]-5,5-dimethylcyclohex-2-ene-1-thione with 2-aminoethanol involves cleavage of the sulfide bond with formation of 3-[(2-hydroxyethyl)-amino]-5,5-dimethylcyclohex-2-ene-1-thione as the major product. The reaction of the same sulfide with ethane-1,2-diamine gave previously unknown 3-(2-[(5,5-dimethyl-3-thioxocyclohex-1-en-1-yl)amino]ethyl}-amino)-5,5-dimethylcyclohex-2-ene-1-thione.
• 1,7-Dithioxo systems. Reaction of bis(5,5-dimethyl-3-thioxo-cyclohex-1-en-1-yl) sulfide with amines
  作者：L. V. Timokhina、O. V. Sokol’nikova、L. V. Kanitskaya、M. P. Yashchenko、M. G. Voronkov

  DOI：10.1134/s1070428008040118

  日期：2008.4

  Reactions of amines (N,N-dimethylethane-1,2-diamine, benzylamine, aniline) with bis(5,5-dimethyl-3-thioxocyclohex-1-en-1-yl) sulfide result in cleavage of the sulfide bond and formation of the corresponding 3-amino-5,5-dimethylcyclohex-2-ene-1-thiones. Aminolysis of bis(5,5-dimethyl-3-oxocyclohex-1-en-1-yl) sulfide occurs at the carbonyl groups with conservation of the divinyl sulfide fragment.
• Timokhina; Panova; Toryashinova, Russian Journal of Organic Chemistry, 1999, vol. 35, # 9, p. 1408 - 1409
  作者：Timokhina、Panova、Toryashinova、Albanov、Sokol'nikova、Voronkov

  DOI：——

  日期：——
• ——
  作者：L. V. Timokhina、G. M. Panova、L. V. Kanitskaya、D. -S. D. Toryashinova、O. V. Sokol'nikova、S. V. Fedorov、M. G. Voronkov

  DOI：10.1023/a:1013100209089

  日期：——

  Hydrolysis of bis[5,5-dimethyl-3-(4-oxa-1-azoniacyclohexylidene)-1-cyclohexenyl] sulfide diperchlorate, as well as of bis(5,5-dimethyl-3-thioxo-1-cyclohexenyl) sulfide, in the system MeCN-Et3N yields a mixture of bis(5,5-dimethyl-3-oxo-1-cyclohexenyl) sulfide and isomeric 5,5-dimethyl-3-oxo-1-cyclohexenyl 3,3-dimethyl-5-oxo-1-cyclohexenyl sulfide. The structure of the products and their ratio were established by H-1 and C-13 NMR and IR spectroscopy.
• ——
  作者：L. V. Timokhina、G. M. Panova、L. V. Kanitskaya、O. V. Sokol'nikova、D. -S. D. Toryashinova、M. G. Voronkov

  DOI：10.1023/a:1013837026547

  日期：——

  Synthetic routes to bis(5,5-dimethyl-3-thioxo-1-cyclohexenyl) sulfide have been studied. The title compound can be obtained by reaction of 3-chloro-5,5-dimethyl-2-cyclohexenethione with sodium thiosulfate and by condensation of 3-mercapto-5,5-dimethyl-2-cyclohexenethione. The reaction of bis(5,5-dimethyl-3-oxo-1-cyclohexenyl) sulfide with hydrogen sulfide and hydrogen chloride yields 3-oxo-3'-thioxobis(5,5-dimethyl-1-cyclohexenyl) sulfide.