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[ CAS No. 89489-53-2 ] {[proInfo.proName]}

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Chemical Structure| 89489-53-2
Chemical Structure| 89489-53-2
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Product Details of [ 89489-53-2 ]

CAS No. :89489-53-2 MDL No. :MFCD09879921
Formula : C6H10O2S Boiling Point : -
Linear Structure Formula :- InChI Key :SCKSQOIXSGPVJS-UHFFFAOYSA-N
M.W : 146.21 Pubchem ID :21598642
Synonyms :

Safety of [ 89489-53-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89489-53-2 ]

* 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 [ 89489-53-2 ]

[ 89489-53-2 ] Synthesis Path-Downstream   1~19

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  • [ 1193-69-7 ]
  • [ 918941-36-3 ]
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  • 4-(tetrahydro-4H-thiopyran-4-cyclohexylidene-4'-ylidene)tetrahydro-4H-thiopyran [ No CAS ]
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  • [ 1072-72-6 ]
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  • [ 195503-41-4 ]
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  • [ 195503-46-9 ]
  • 6
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  • N-[4-(Methyl-phenyl-thiocarbamoyl)-tetrahydro-thiopyran-4-yl]-benzamide [ No CAS ]
  • 7
  • [ 89489-53-2 ]
  • [ 195503-57-2 ]
  • 8
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  • 2-[4-(2-Benzyloxycarbonylamino-2-methyl-propionylamino)-tetrahydro-thiopyran-4-carbonyl]-amino}-2-methyl-propionic acid [ No CAS ]
  • 9
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  • [ 195503-56-1 ]
  • 10
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  • [ 195503-58-3 ]
  • 11
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  • 1-tetrahydrothiopyran-4-yl-propan-1-ol [ No CAS ]
  • 12
  • [ 89489-53-2 ]
  • 1-tetrahydrothiopyran-4-yl-ethane-1,2-diol [ No CAS ]
  • 13
  • [ 89489-53-2 ]
  • [ 858822-78-3 ]
  • 15
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  • 1-tetrahydrothiopyran-4-yl-propan-1-one-(2,4-dinitro-phenylhydrazone) [ No CAS ]
  • 16
  • [ 89489-53-2 ]
  • [ 18107-18-1 ]
  • [ 128094-82-6 ]
YieldReaction ConditionsOperation in experiment
In methanol; hexane; toluene; Preparation 31: Methyl tetrahvdro-2W-thiopyran-4-carboxylate;Trimethylsilyl diazomethane (2M in hexane, 45.4ml., 90.8mmol) was added dropwise to a solution of the acid from preparation 30 (6.65g, 45mmol) in toluene (20OmL) and MeOH (67ml_). Once addition was complete, the reaction was quenched by the addition of AcOH (sufficient to cause de-colourisation of the solution). The mixture was concentrated under reduced pressure and the residue purified by column chromatography on silica gel using DCM:Me0H (98:2 to 95:5) to afford the title compound as a white solid, 6.95g.1H-NMR (CDCI3, 400MHz): δ 1.85 (m, 2H), 2.20 (m, 2H), 2.40 (m, 2H, 2.66 (m, 4H), 3.66 (s, 3H).
  • 17
  • [ 89489-53-2 ]
  • [ 100277-27-8 ]
YieldReaction ConditionsOperation in experiment
A solution of borane dimethylsulfide complex (73.5 ml, 775 mmol) in anhydrous tetrahydrofuran (1.5 L) was treated dropwise over 15 min with a solution of tetrahydrothiopyran-4-carboxylic acid (646 mmol) in anhydrous tetrahydrofuran (300 ml). The mixture was then heated to 70C for 2 h, cooled to room temperature and quenched by dropwise addition of water until effervesence ceased. A further portion of water (500 ml) was then added and the tetrahydrofuran removed in-vacuo. The residue was then acidified with dilute hydrochloric acid solution and extracted into dichloromethane (3 x 500 ml). The combined organic layers were then dried over sodium sulfate and the solvent removed in-vacuo to give (tetrahydrothiopyran-4-yl)- methanol as a brown oil (90.18 g, 646 mmol).
Step C: (Tetrahydro-thiopyran-4-yl)-methanol A solution of borane dimethylsulfide complex (73.5 ml, 775 mmol) in anhydrous tetrahydrofuran (1.5 L) was treated dropwise over 15 min with a solution of <strong>[89489-53-2]tetrahydro-thiopyran-4-carboxylic acid</strong> (646 mmol) in anhydrous tetrahydrofuran (300 ml). The mixture was then heated to 70 C. for 2 h, cooled to room temperature and quenched by dropwise addition of water until effervescence ceased. A further portion of water (500 ml) was then added and the tetrahydrofuran removed in vacuo. The residue was then acidified with dilute hydrochloric acid solution and extracted into dichloromethane (3*500 ml). The combined organic layers were then dried over sodium sulfate and the solvent removed in vacuo to give (tetrahydro-thiopyran-4-yl)-methanol as a brown oil (90.2 g, 646 mmol).
Step C: (Tetrahydro-thiopyran-4-yl)-methanol A solution of borane dimethylsulfide complex (73.5 ml, 775 mmol) in anhydrous tetrahydrofuran (1.5 L) was treated dropwise over 15 min with a solution of <strong>[89489-53-2]tetrahydro-thiopyran-4-carboxylic acid</strong> (646 mmol) in anhydrous tetrahydrofuran (300 ml). The mixture was then heated to 70 C for 2 h, cooled to room temperature and quenched by dropwise addition of water until effervescence ceased. A further portion of water (500 ml) was then added and the tetrahydrofuran removed in vacuo. The residue was then acidified with dilute hydrochloric acid solution and extracted into dichloromethane (3 x 500 ml). The combined organic layers were then dried over sodium sulfate and the solvent removed in vacuo to give (tetrahydro-thiopyran-4-yl)- methanol as a brown oil (90.2 g, 646 mmol).
Step C: (Tetrahyd ro-thiopyran-4-yl)-methanol A solution of borane dimethylsulfide complex (73.5 ml, 775 mmol) in anhydrous tetrahydrofuran (1.5 L) was treated dropwise over 15 min with a solution of <strong>[89489-53-2]tetrahydro-thiopyran-4-carboxylic acid</strong> (646 mmol) in anhydrous tetrahydrofuran (300 ml). The mixture was then heated to 70 C. for 2 h, cooled to room temperature and quenched by dropwise addition of water until effervescence ceased. A further portion of water (500 ml) was then added and the tetrahydrofuran removed in vacuo. The residue was then acidified with dilute hydrochloric acid solution and extracted into dichloromethane (3*500 ml). The combined organic layers were then dried over sodium sulfate and the solvent removed in vacuo to give (tetrahydro-thiopyran-4-yl)-methanol as a brown oil (90.2 g, 646 mmol).
With borane-THF; In tetrahydrofuran; at 20 - 70℃; A 25 mL single-necked flask was charged with tetrahydrothiopyran-4-formic acid (0.36 g), and anhydrous tetrahydrofuran (5 mL) as the reaction solvent. Under a condition of room temperature, a solution of borane in tetrahydrofuran (1 M, 3.7 mL) was added dropwise. After the completion of the addition, the mixture was reacted at 70C for 2 h. A sample was taken, and TLC detection showed that the spots of the raw materials disappeared and the reaction was complete. Methanol was added dropwise to the reaction system to quench the reaction. The resulting mixture was concentrated under reduced pressure to obtain 0.34 g of tetrahydrothiopyran-4-methanol (crude product), which was directly used for the reaction in the next step.
378 mg With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 70℃; for 2h;Inert atmosphere; A solution of tetrahydro-2H-thiopyran-4-carbonitrile (S4) (836 mg, 6.57 mmol) in ethanol (2.5 mL) was added to a solution of NaOH (2.63 g, 65.7 mmol) in EtOH (15 mL) and H2O (7.5 mL). The mixture was heated under reflux and stirred for 6 h. After cooling to 0 C, conc. HCl was added to adjust the pH to 2 and EtOH was then evaporated. The residue was extracted with CH2Cl2, dried over MgSO4, and evaporated to afford a brown crude product. A solution of BH3·SMe2 (667 μL, 7.02 mmol) in THF (12 mL) was introduced in a dropwise manner to a solution of the crude product in THF (6 mL) at 0 C. The mixture was then heated to 70 C for 2 h, cooled to room temperature, and quenched by dropwise addition of water. THF was then removed in vacuo and the residue was acidified with 20% HCl aq. and extracted with CH2Cl2. The organic layer was washed with brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography (AcOEt/hexane = 1/4) to afford (tetrahydro-2H-thiopyran-4-yl) methanol (1k) (378 mg, 2.86 mmol, 44% (2 steps)) as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ: 3.46 (d, J = 5.8 Hz, 2H), 2.73-2.59 (m, 4H), 2.09 (dq, J = 13.0, 3.0 Hz, 2H), 1.58 (br s,1H), 1.56-1.49 (m, 1H), 1.39 (tdd, J = 12.3, 11.7, 3.5 Hz, 2H). 13C-NMR (100 MHz, CDCl3) δ: 67.9, 39.9, 30.5, 28.2. IR (neat, cm-1): 3366, 2915, 1428, 1270, 1036. MS m/z: 132 ([M]+), 86 (100%). HRMS (EI): Calcd for C6H12OS 132.0609, found: 132.0599.

  • 18
  • [ 89489-53-2 ]
  • [ 27246-81-7 ]
  • [ 1190861-82-5 ]
YieldReaction ConditionsOperation in experiment
60% Oxalyl chloride (1.20 mL, 14.2 mmol) was added dropwise to a stirred solution of <strong>[89489-53-2]tetrahydro-2H-thiopyran-4-carboxylic acid</strong> (, 2.00 g, 13.7 mmol) in dichloromethane (25 mL). Then, two drops of N,N'-dimethylformamide were added and stirring was continued. After 1.5 hours, the resultant solution was added dropwise over 30 minutes to a stirred, cooled (ice-bath) solution of (3-bromophenyl)hydrazine hydrochloride (3.05 g, 13.7 mmol) and triethylamine (4.20 mL, 30.1 mmol) in dichloromethane (40 mL). After the addition, the mixture was warmed to room temperature and stirred for two hours. The mixture was then concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with 4% aqueous sodium hydrogen carbonate solution, dried (MgSO4) and evaporated. The residue was triturated with diethyl ether and the solid was filtered and dried to give the title compound (2.57 g, 60%) as an off-white solid. LRMS (m/z): 315/317 (M+1)+. 1H-NMR δ (DMSO-d6): 1.62-1.76 (m, 2H), 2.00-2.07 (m, 2H), 2.28-2.37 (m, 1 H), 2.63-2.67 (m, 4H), 6.66 (d, J=9.0 Hz, 1 H), 6.79 (t, J=3.0Hz, 1 H), 6.84 (d, J=9.0 Hz, 1H), 7.08 (t, J=9.0 Hz, 1H), 8.00 (brs, 1H), 9.71 (brs, 1H).
  • 19
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  • [ 1257249-91-4 ]
  • [ 1257249-79-8 ]
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