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Chemical Structure| 2757-37-1 Chemical Structure| 2757-37-1

Structure of 2757-37-1

Chemical Structure| 2757-37-1

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Product Details of [ 2757-37-1 ]

CAS No. :2757-37-1
Formula : C24H50S2
M.W : 402.78
SMILES Code : CCCCCCCCCCCCSSCCCCCCCCCCCC
English Name :1,2-Didodecyldisulfane
MDL No. :MFCD00039866
InChI Key :GAYUSSOCODCSNF-UHFFFAOYSA-N
Pubchem ID :151040

Safety of [ 2757-37-1 ]

Computational Chemistry of [ 2757-37-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 26
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 23
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 132.66
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

50.6 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

6.77
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

12.08
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

10.21
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

7.33
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

10.03
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

9.28

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-8.43
Solubility 0.0000015 mg/ml ; 0.0000000037 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-13.15
Solubility 0.0 mg/ml ; 0.0 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Insoluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-9.7
Solubility 0.0000000804 mg/ml ; 0.0000000002 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-0.18 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

1.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

1.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

1.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<3.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

4.7

Application In Synthesis of [ 2757-37-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2757-37-1 ]

[ 2757-37-1 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 765-15-1 ]
  • [ 2757-37-1 ]
YieldReaction ConditionsOperation in experiment
100% With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;
75% With samarium diiodide In tetrahydrofuran for 0.25h; Ambient temperature;
75% With samarium; titanium tetrachloride In tetrahydrofuran at 0℃;
With pyridine; acetic acid at 130 - 135℃; Versetzen der Reaktionsloesung mit Eiswasser;

  • 2
  • [ 2757-37-1 ]
  • [ 112-55-0 ]
YieldReaction ConditionsOperation in experiment
86% With hydrogen In toluene for 0.5h; Heating;
With sulfuric acid; zinc
With sodium hydrogensulfide; water
94 % Spectr. With RhCl(PPh3)3; hydrogen In toluene at 100℃; for 2h;

  • 3
  • [ CAS Unavailable ]
  • [ 2757-37-1 ]
YieldReaction ConditionsOperation in experiment
With tetrachloromethane; bromine
With 4-nitrobenzoic acid methyl ester In sulfolane at 140℃; for 2h;
  • 4
  • [ 112-55-0 ]
  • [ 2757-37-1 ]
YieldReaction ConditionsOperation in experiment
100% With aluminum oxide; dimethyl sulfoxide at 70℃; for 2.5h;
100% With aluminum oxide; sodium iodate In hexane at 20℃; for 1.5h;
100% With iodine; triethylamine In tetrahydrofuran at 0 - 25℃; Inert atmosphere;
99% With barium manganate In chloroform for 10h; Ambient temperature; other thiols;
99% With barium manganate In chloroform for 10h; Ambient temperature;
99% With oxygen In methanol at 40℃; for 2.5h;
99% With polyvinylpolypyrrolidonium tribromide In ethanol at 20℃; for 1.75h; Green chemistry; General procedure: A 25 mL round-bottom flask was charged with thiol (1 mmol), polyvinylpolypyrrolidoniume tribromide (1.2 gr), and EtOH(5 mL) as solvent. The reaction mixture was stirred at room temperature, and the progressof the reaction was monitored by TLC. After completion of the reaction, corresponding disulfides easily obtained by passing of reaction mixture through a short column using dichlromethane and acetone (95:5) as eluent.
99% With diphenyldisulfane; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 0℃; for 0.0833333h;
98% With air In hexane at 30℃; for 2h;
98% With sulfuryl dichloride for 0.5h; cooling;
98% With cerium(III) chloride; iodine; pyrographite In ethyl acetate at 20℃; for 0.8h;
98% With 5,5-dimethyl-2-thioxo-1,3,2-dioxophosphorinane-2-sulfenyl bromide; triethylamine In dichloromethane at -30℃;
98% With bis(4-methoxyphenyl)telluride; 5,15,10,20-tetraphenylporphyrin In dichloromethane at 0℃; for 0.25h; Irradiation;
98% With iodine; oxygen In ethyl acetate at 70℃; for 4h; 1 Example 1 A catalytic amount of elemental iodine (3.8 mg, 0.015 mmol), 8.0 mL of solvent ethyl acetate and compound 1a (60.7 mg, 0.300 mmol) were sequentially added to a 25 mL single-necked round-bottomed flask. Oxygen was introduced into the reaction vessel, the reaction mixture was heated to 70° C. using an oil bath, and stirred for 4 h using a magnetic stirring device. Then, the single-neck round-bottomed flask was taken out from the oil bath and cooled. Ethyl acetate (15 mL) was added to expand the volume, and the organic phase was washed with a 0.1 mol/L aqueous hydrochloric acid solution. The aqueous phase was extracted twice with a total of 40 mL of ethyl acetate, and the organic phases were combined. The combined organic phases were dried over anhydrous magnesium sulfate. After drying, magnesium sulfate was removed by filtration, and the organic phase was concentrated using a rotary evaporator to obtain 59.2 mg of the target compound 2a with a yield of 98%.
97% With iodoacetophenone; potassium carbonate In ethanol for 0.166667h; Ambient temperature;
97% With sodium bromide In methanol; water; benzene Ambient temperature; electrooxidation;
97% With aluminium trichloride; tetrabutylammonium periodite In chloroform for 0.216667h; Ambient temperature;
97% With dihydrogen peroxide; sodium iodide In ethyl acetate at 20℃; for 0.5h;
97.5% With sodium hypochlorite at 20℃; for 18h;
97% With iodine; potassium iodide In water at 25℃; Sonication;
95% In acetonitrile Ambient temperature;
95% With clay supported NH4NO3 "Clayan" for 0.0277778h; microwave irradiation;
95% With ammonium peroxydisulfate at 20℃; for 21h;
95% With sodium methylate In methanol at 20℃; for 9h; Green chemistry; A typical procedure for the preparation of symmetrical disulfides General procedure: A variety of thiols (10mmol) were added into sodium methoxide 30 wt. % in methanol(1.85 mL, 10mmol) (NaOMe/MeOH-30), and the solution was stirred at room temperatureunder air atmosphere. After completion of the reaction, the desired products wereextracted with ethyl acetate or n-hexane (3×2mL). The collected extracts were driedover Na2SO4 and concentrated under reduced pressure. The pure symmetrical disulfideswere obtained as liquids or solids. The known and new products were characterized andidentified by melting point, FT-IR, 1HNMR and 13C NMR, and mass analysis.
94% With iodine; triethylamine In tetrahydrofuran at 0 - 20℃;
94% With cyclopentadienyl manganese tricarbonyl In cyclohexane at 25℃; for 2.5h; Inert atmosphere; UV-irradiation;
93% With oxygen; vanadium(V) oxychloride In ethyl acetate at 20℃; for 22h;
93% With 1,4-diazabicyclo[2.2.2]octane N,N′-dioxide In acetonitrile for 3h; Heating;
92% With sodium hydroxide; cobalt phthalocyaninetetrasulphonamide; oxygen In water at 20℃; for 0.666667h;
92% With phenyltrimethylammonium tribromide In tetrahydrofuran at 30℃; for 6h; General experimental procedure (C) for the synthesis of disulfane: General procedure: To a well stirred solution of Thiols (1equiv.) in THF Phenyl Trimethyl ammonium Tribromide (PTAB) (0.5 equiv) was added and the reaction was stirred at room tempearature for 4-8 hrs. After completion of the reaction which was monitored by TLC, The reaction mixture was quenched with distilled water and extracted with ethyl acetate (3X3ml). The organic fraction was washed with saturated brine solution and dried over oven dried anhydrous sodium sulphate. The solvent was evaporated under reduced pressure. The residual crude mass was subjected to a short silica gel column filtration (petroleum ether/ethyl acetate) afforded the desired disulfane as the pure product.
90% With sodium hypochlorite In acetonitrile at 20℃; for 0.0833333h;
90% With potassium bromate; hexaammonium heptamolybdate tetrahydrate In water; acetonitrile at 20℃; for 0.5h; Typical Procedure General procedure: 4-chlorothiophenol (0.145 g, 1 mmol) was added to a heterogeneous mixture of KBrO3 (0.167 g, 1 mmol), (NH4)6Mo7O24·4H2O (0.124 g, 10 mmol%), and CH3CN/H2O (7:3) (5 mL) and the mixture was stirred under a hood for 4 min at ambient atmosphere and room temperature. The progress of the reaction was monitored by TLC (eluent: EtOAc/n-C6H14, 1/13). After completion, CH2Cl2 (20 mL) was added and the reaction mixture was filtered. The filtrate was washed with 5% NaOH, water, and dried over anhydrous MgSO4. Finally, evaporation of the solvent gave the product with sufficient purity formost purposes
90% With hydrogenchloride; iodine In dimethyl sulfoxide VII EXAMPLE VII EXAMPLE VII A mixture of 9 ml of DMSO (127 mmole), 12 ml of 1-dodecanethiol (50 mmole), 0.1 ml of 37 percent hydrochloric acid (1.2 mmole), and 10.8 mg of iodine (0.085 mmole as HI) was heated by a bath, while stirring magnetically, at about 60°C. After one and a fourth hours, the lower phase became amber colored. The mixture was cooled with stirring to produce fine crystals. These were filtered off and rinsed with DMSO. Recrystallization from acetone gave 9.02 g of didodecyl disulfide (90 percent of theory). Mp, 33°-5°C. (reported, 33°-4°C.).
89% With activated carbon (Charcoal Activated); air In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 8h;
89% With bromopentacarbonylmanganese(I); oxygen In cyclohexane at 20℃; for 2h; UV-irradiation; chemoselective reaction;
86% In dimethyl sulfoxide at 70℃; for 24h;
84% With oxygen; sodium carbonate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 0.5h;
84% With 1-butyl-3-methylimidazolium methoxyselenite at 60℃; for 4h; General procedure for the oxidation of thiols with [bmim][SeO2(OCH3)]: Method A: In a Schlenk tube under open atmosphere and at room temperature, the corresponding thiol (1.0 mmol) was added to [bmim][SeO2(OCH3)]10 (1.0 mL). The reaction mixture was allowed to stir at 60 °C for the time indicated in Table 1. The progress of the reaction was monitored by TLC. Method B: In a 10 mL glass vial equipped with a small magnetic stirring bar, containing 1.0 mL of [bmim][SeO2(OCH3)] was added the thiol (1.0 mmol). The vial was tightly sealed with an aluminum/Teflon crimp top. The mixture was then irradiated in a microwave reactor (CEM Explorer) for the time indicated in Table 2 at 30 °C (temperature was measured with an IR sensor on the outer surface of the reaction vial), using an irradiation power of 100 W and pressure of 150 psi. After the reaction was complete, the product was extracted by successive washings with petroleum ether (3 × 5 mL), dried over MgSO4, and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate/hexanes as the eluent.
81% With oxygen; cesium fluoride In acetonitrile at 20℃;
81% With periodic acid; sodium hydrogensulfite In tetrachloromethane; water at 20℃;
80% With Fe(III) montmorillonite at 45℃; for 10h; pH 7.2 (phosphate buffer);
80% With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium In dichloromethane at -15 - 20℃;
80% With Al2O3-supported KF In acetonitrile at 20℃; for 0.333333h; Green chemistry; General Procedure General procedure: To a mixture of 11-mercapto undecene-1-ol (0.5 g;2.4 mmol) in acetonitrile (6 mL), KF-Al2O3 (1 g) wasadded and the reaction mixture was stirred at RT for24 min. After completion of the reaction (monitoredby TLC), the KF-Al2O3 was filtered off. Evaporationof the solvent under reduced pressure followed bychromatography over silica gel using light petroleumethylacetate as eluent furnished the correspondingpure disulfide in 70-82% yield.
75% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; copper dichloride In toluene at 110℃; for 12h; 13 Step Synthesis of didecyl disulfide To a reaction flask equipped with 3mL of toluene were added sequentially 0. 05mmol of TEMPO, 0. 05 mmol of CuCl2, 1 mmol dodecanethiol, substituted with an oxygen atmosphere, reflux the reaction 12 hours, the reaction was complete gussets. Direct mix sample through the column. The product was obtained in 75% yield
73% With epolactaene; sodium hydrogencarbonate In methanol; water at 20℃; for 0.5h; Inert atmosphere; 5.3. General procedure for the formation of disulfides (Table 2) General procedure: To a solution of 1 (10 mg, 26 μmol) and thiol (2.2 mol equiv) in degassed MeOH (1.0 mL) was added 0.5 M aqueous solution of NaHCO3 (1.0 mL) at room temperature. The mixture was stirred at room temperature under a nitrogen atmosphere until no further change in TLC was observed. The reaction was quenched by the addition of 1 M HCl aqueous solution, and the mixture was diluted with EtOAc. The layers were separated, the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by column chromatography to give the corresponding disulfide. The structures of diphenyl disulfide, 2,2'-dipyridyl disulfide, n-dihexyl disulfide and n-didodecyl disulfide were confirmed by MS analyses as well as comparison of the 1H NMR data with those of the authentic disulfides.
71% With tert.-butylnitrite; oxygen In 1,2-dichloro-ethane at 50℃; for 6h; Sealed tube; Green chemistry; Typical procedure for disulfides (2a) General procedure: A sealed tube (90 mL) equipped with a magnetic stirring bar and an O2 balloon was charged with dichloroethane (DCE, 20 mL), thiophenol (1a, 4 mmol, 0.44 g) and TBN (0.16 mmol, 4 mol%, 19.2 mL). Then the tube was placed in an oil bath, which was preheated to 50°C. The mixture was stirred for 1 h until starting material was completely consumed as monitored by GC and TLC. After removing the solvent, the residue was purified by column chromatography on silica gel to give the desired diphenyl disulfide (2a, 90%, 0.394 g) as a white solid.
70% With KF/Al2O3 at 70℃; for 10h;
70% With graphene oxide In tetrahydrofuran at 60℃;
70% With iodine; dimethyl sulfoxide In neat (no solvent) at 25℃; for 0.166667h; Microwave irradiation; Sealed tube; 3. General procedure for synthesis of aliphatic disulfides 2l-n under microwaves irradiation General procedure: In specific microwave tube (10.0 mL), was added iodine (51.0 mg, 20.0 mol%), DMSO (37 µL, 1.0 mmol) and thiol (1.0 mmol), The sealed reaction tube was placed in the microwave cavity and a maximum irradiation power of 100 W was applied. When the temperature reach 25 °C the reaction was stirred for 10 minutes. After cooling the reaction system to room temperature it was quenched with ethyl acetate and the aqueous layer was extracted with Na2S2O3 (3 x 20.0 mL). The organic phase was dried over MgSO4, filtered, and the solvent was removed reduced pressure. The crude product was purified by flash column chromatography eluting with an appropriate mixture of hexane/ethyl acetate.
50% With ammonium thiocyanate; Benzoylformic acid In acetonitrile for 7h; Irradiation; Green chemistry;

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[25]Ishizuka, Kentaro; Seike, Hirofumi; Hatakeyama, Takuji; Nakamura, Masaharu [Journal of the American Chemical Society, 2010, vol. 132, # 38, p. 13117 - 13119].
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[27]Kirihara, Masayuki; Okubo, Kumiko; Uchiyama, Tomoyuki; Kato, Yoko; Ochiai, Yuta; Matsushita, Shinya; Hatano, Akihiko; Kanamori, Kan [Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 625 - 627].
[28]Salehi, Peyman; Zolfigol, Mohammad Ali; Tolami, Leila Bazaz [Phosphorus, Sulfur and Silicon and the Related Elements, 2004, vol. 179, # 9, p. 1777 - 1781].
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[32]Bayraq, Samad Shoghpour; Nikseresht, Ahmad; Khosravi, Iman [Phosphorus, Sulfur and Silicon and the Related Elements, 2013, vol. 188, # 9, p. 1236 - 1243].
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  • 5
  • [ 2757-37-1 ]
  • [ 112-40-3 ]
YieldReaction ConditionsOperation in experiment
50 % Chromat. With sodium tetrahydroborate; cobalt(II) chloride In tetrahydrofuran; methanol at 0℃; for 0.25h;
With hydrogenchloride; iron; cadmium(II) chloride In water for 0.0333333h; Heating;
  • 6
  • [ CAS Unavailable ]
  • [ 2757-37-1 ]
YieldReaction ConditionsOperation in experiment
90% With samarium; ammonium chloride In tetrahydrofuran; water at 20℃; for 4h;
90% With samarium In water at 90℃; for 4h;
88% With samarium diiodide In tetrahydrofuran for 0.5h; Ambient temperature;
84% With samarium; iodine In tetrahydrofuran for 4h; Ambient temperature;
83% With samarium; chloro-trimethyl-silane; water In tetrahydrofuran at 20℃; for 5h;
83% In tetrahydrofuran; water at 20℃; for 4h;
With water; iodine In ethanol Yield given;
With samarium diiodide In tetrahydrofuran

  • 7
  • [ 2757-37-1 ]
  • [ 80859-83-2 ]
  • [ 161564-32-5 ]
YieldReaction ConditionsOperation in experiment
80% In dichloromethane at 30℃; for 3h; Irradiation;
YieldReaction ConditionsOperation in experiment
With ethanol; iodine
With 1,4-dioxane; sulfuric acid; dihydrogen peroxide at 5℃;
  • 9
  • [ 54187-96-1 ]
  • [ 2757-37-1 ]
  • [ 158200-32-9 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: didodecyl disulfide With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran at 40℃; for 1h; Stage #2: 1-(chloromethyl)-1H-benzotriazole In tetrahydrofuran at 20℃; for 14h;
  • 10
  • [ 87-90-1 ]
  • [ 112-55-0 ]
  • [ 2757-37-1 ]
  • [ 108-80-5 ]
YieldReaction ConditionsOperation in experiment
80% With pyridine; water; benzoic acid In dichloromethane; acetonitrile at 40℃;
  • 12
  • [ 2757-37-1 ]
  • [ CAS Unavailable ]
  • [ 858357-62-7 ]
YieldReaction ConditionsOperation in experiment
54% Stage #1: propargyl alcohol With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.5h; Stage #2: didodecyl disulfide In tetrahydrofuran; hexane at 20℃; for 3h;
  • 13
  • [ 2757-37-1 ]
  • [ 143-15-7 ]
  • [ 2469-45-6 ]
YieldReaction ConditionsOperation in experiment
91% With RhCl(PPh3)3; hydrogen; triethylamine In tetrahydrofuran at 50℃; for 24h;
86% With hydrogen; triethylamine In tetrahydrofuran at 65℃; for 24h; Inert atmosphere; Green chemistry; Reactions of disulfides and diselenides with alkyl halides; general procedure General procedure: A 25 mL, three-necked round-bottom flask equipped with a refluxcondenser and a magnetic stir bar was charged sequentially withSiO2-P-RhCl(PPh3)2 (16 mg, 0.006 mmol), disulfide or diselenide(0.2 mmol), alkyl halide (0.44 mmol), THF (1.0 mL), and Et3N(0.2 mL) under argon. Then hydrogen was introduced to the resultingsuspension. The mixture was stirred at 65 °C for 24 h. After beingcooled to room temperature, the mixture was diluted with Et2O (10 mL)and filtered. The SiO2-P-RhCl(PPh3)2 complex was washed withTHF (2 × 5 mL) and Et2O (2 × 5 mL) and reused in the next run. Theether solution was concentrated under a reduced pressure, and theresidue was purified by preparative TLC (hexane) to afford the desiredproduct.
  • 14
  • [ CAS Unavailable ]
  • [ 112-55-0 ]
  • [ 2757-37-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In tetrachloromethane; water 2 EXAMPLE 2 EXAMPLE 2 202 g (1 mol) n-dodecyl mercaptan, 22 g (0.55 mol) sodium hydroxide, 100 ml water and 0.6 g (1.5 mmol) tricapryl methyl ammonium chloride are reacted as in Example 1 with 77 g (0.5 mol) tetrachloromethane. Yield of di-n-dodecyl disulfide: 198 g (99%).
 

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