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Chemical Structure| 10521-06-9 Chemical Structure| 10521-06-9

Structure of 10521-06-9

Chemical Structure| 10521-06-9

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Product Details of [ 10521-06-9 ]

CAS No. :10521-06-9
Formula : C8H12O3
M.W : 156.18
SMILES Code : O=C(CCCCCC1)OC1=O
English Name :Oxonane-2,9-dione
MDL No. :MFCD18253479

Safety of [ 10521-06-9 ]

Application In Synthesis of [ 10521-06-9 ]

* 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 [ 10521-06-9 ]

[ 10521-06-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1119-34-2 ]
  • [ 10521-06-9 ]
  • suberoyl arginine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With water; sodium hydrogencarbonate; at 4℃; for 0.333333h; General procedure for the preparation of the SA derivatives: To a solution of amino acid hydrochloride (1 equiv) and sodium bicarbonate (2 equiv) in water (ca. 1 M) was added the carboxylic anhydride (1.1 equiv) at 4 C slowly. After stirring for 20 min, a few drops of concentrated ammonia-water were added to adjust the pH to 8. The solution was then filtered and washed three times with dichloromethane. The sample was freeze-dried and purified by CI 8 reverse-phase silica gel chromatography. Suberoyl arginine: 'H NMR (500 MHz, D20) delta 4.19-4.17 (dd, 1H), 3.03 (t, 2H), 2.19 (t, 2H), 2.11 (t, 2H), 1.79-1.71 (m, 1H), 1.62-1.55 (m, 1H), 1.49-1.37 (m, 6H), 1.14-1.12 (m, 4H); XH NMR (500 MHz, DMSO-i) delta 4.14-4.11 (dd, 1H), 3.09 (t, 2H), 2.17 (t, 2H), 2.10 (t, 2H), 1.71-1.67 (m, 1H), 1.62-1.57 (m, 1H), 1.49 (m, 6H), 1.22 (m, 4H); 13C NMR (125 MHz, D20) delta 179.2, 177.3, 175.5, 156.6, 52.3, 40.6, 35.3, 33.8, 27.9, 27.8, 27.7, 25.2, 24.6, 24.3; 13C NMR (125 MHz, DMSO-i) delta 175.3, 174.1, 173.5, 157.2, 52.0, 39.3, 35.6, 28.9, 28.5, 25.9, 25.8, 25.0; MS(APCI) calcd for Ci4H27N405 (M+H)+ 331.2, found 331.1; calcd for Ci4H25N405 (M-fff 329.2, found 329.2.
  • 2
  • [ 10521-06-9 ]
  • [ 946150-57-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 2: 4-methyl-morpholine / 1-methyl-pyrrolidin-2-one / -3 °C / Inert atmosphere 3: hydroxylamine hydrochloride / 1-methyl-pyrrolidin-2-one / 0.92 h / -10 °C / pH 5.5 / Inert atmosphere; Large scale
Multi-step reaction with 3 steps 1: triethylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 2: 4-methyl-morpholine / 1-methyl-pyrrolidin-2-one / -3 °C / Inert atmosphere 3: hydroxylamine / 1-methyl-pyrrolidin-2-one; acetic acid; water / 16 h / -20 - 10 °C / Inert atmosphere
  • 4
  • [ 10521-06-9 ]
  • [ 39876-39-6 ]
  • [ 3094521-06-6 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane at 110℃; for 5h; General procedure for the synthesisof target compounds 13a-13d and 18a-18f General procedure: N-Hydroxy-5-oxo-5-(1,3,4,5-tetrahydro-2H-pyrido[4,3-b]-indol-2-yl)pentanamide (13a, C16H19N3O3)To a solutionof phenylhydrazine hydrochloride (1000.0 mg, 6.92 mmol)in 35 cm3ethanol was added 4,4-piperidinediol hydrochloride.The mixture was stirred for 10 h at 80 . The reactionsolution was adjusted to alkaline by adding sodiumhydroxide aqueous solution, the product was precipitated,and tetrahydro-γ-carboline was obtained by extraction andfiltration. Tetrahydro-γ-carboline (500.0 mg, 2.91 mmol)was dissolved in 1,4-dioxane (10 cm3)and added with glutaricanhydride (332.0 mg, 2.91 mmol). The reaction wasreacted at 110 for 5 h, and compound 11 was obtained byconventional treatment. The intermediate 11 was dissolvedin methanol (20 cm3),then dripped into SOCl2and reactedat 75 for 2 h to obtain the intermediate 12 (350.0 mg).A solution of hydroxylamine hydrochloride (1210.0 mg,7.25 mmol) in 10 cm3of methanol was treated with KOH(900.0 mg, 17.25 mmol). This mixture was stirred for 10 minat a temperature of 40 , then cooled to 0 and filtered.Compound 12 (200.0 mg, 0.69 mmol) was introduced into reaction was stirred at ambient temperature for one hour.Subsequently, the solvent was evaporated under reducedpressure, and the residue was diluted with a saturated aqueoussolution of NH4Cl,followed by extraction with ethylacetate. The organic phase was washed with brine, driedusing Na2SO4,and concentrated. The resulting mixture wasevaporated to dryness and then subjected to column chromatographyfor purification, yielding compound 13a. Yield24.2%; 1H NMR (600 MHz, DMSO-d6): δ = 10.91/10.89(br s, 1H), 10.36/10.36 (br s, 1H), 8.67/8.67 (br s, 1H,H-5), 7.43/7.41 (d, J = 7.8, 7.8 Hz, 1H, H-6), 7.29/7.28(d, J = 7.8 Hz, 1H, H-9), 7.05-7.02/7.05-7.02 (m, 1H,H-8), 6.98-6.94/6.94 (m, 1H, H-7), 4.64/4.64 (s, 2H, H-1),3.85/3.77 (t, J = 5.4 Hz, 2H, H-3), 2.85/2.75 (t, J = 5.4 Hz,2H, H-4), 2.45-2.41/2.45-2.41 (m, 2H), 2.02/2.02 (t, J =7.2 Hz, 2H), 1.79-1.72/1.79-1.72 (m, 2H) ppm; 13C NMR(150 MHz, DMSO-d6): δ = 170.98/170.69, 168.96/168.96,135.92/135.83 (C-5a), 132.98/132.36 (C-4a), 125.29/125.03(C-9a), 120.66/120.63 (C-7), 118.53/118.50 (C-8),117.27/117.18 (C-9), 110.95/110.92 (C-6), 105.91/105.52(C-9b), 42.57/42.10 (C-3), 38.94/38.75 (C-1), 32.33/31.88,31.88/31.65, 23.79/22.89 (C-4), 21.01/20.86 ppm; HRMS(ESI): m/z calcd for [C16H19N3O3 + H]+302.1426, found302.1503.
  • 5
  • [ 19685-84-8 ]
  • [ 10521-06-9 ]
  • [ 3094521-08-8 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane at 110℃; for 5h; General procedure for the synthesisof target compounds 13a-13d and 18a-18f General procedure: N-Hydroxy-5-oxo-5-(1,3,4,5-tetrahydro-2H-pyrido[4,3-b]-indol-2-yl)pentanamide (13a, C16H19N3O3)To a solutionof phenylhydrazine hydrochloride (1000.0 mg, 6.92 mmol)in 35 cm3ethanol was added 4,4-piperidinediol hydrochloride.The mixture was stirred for 10 h at 80 . The reactionsolution was adjusted to alkaline by adding sodiumhydroxide aqueous solution, the product was precipitated,and tetrahydro-γ-carboline was obtained by extraction andfiltration. Tetrahydro-γ-carboline (500.0 mg, 2.91 mmol)was dissolved in 1,4-dioxane (10 cm3)and added with glutaricanhydride (332.0 mg, 2.91 mmol). The reaction wasreacted at 110 for 5 h, and compound 11 was obtained byconventional treatment. The intermediate 11 was dissolvedin methanol (20 cm3),then dripped into SOCl2and reactedat 75 for 2 h to obtain the intermediate 12 (350.0 mg).A solution of hydroxylamine hydrochloride (1210.0 mg,7.25 mmol) in 10 cm3of methanol was treated with KOH(900.0 mg, 17.25 mmol). This mixture was stirred for 10 minat a temperature of 40 , then cooled to 0 and filtered.Compound 12 (200.0 mg, 0.69 mmol) was introduced into reaction was stirred at ambient temperature for one hour.Subsequently, the solvent was evaporated under reducedpressure, and the residue was diluted with a saturated aqueoussolution of NH4Cl,followed by extraction with ethylacetate. The organic phase was washed with brine, driedusing Na2SO4,and concentrated. The resulting mixture wasevaporated to dryness and then subjected to column chromatographyfor purification, yielding compound 13a. Yield24.2%; 1H NMR (600 MHz, DMSO-d6): δ = 10.91/10.89(br s, 1H), 10.36/10.36 (br s, 1H), 8.67/8.67 (br s, 1H,H-5), 7.43/7.41 (d, J = 7.8, 7.8 Hz, 1H, H-6), 7.29/7.28(d, J = 7.8 Hz, 1H, H-9), 7.05-7.02/7.05-7.02 (m, 1H,H-8), 6.98-6.94/6.94 (m, 1H, H-7), 4.64/4.64 (s, 2H, H-1),3.85/3.77 (t, J = 5.4 Hz, 2H, H-3), 2.85/2.75 (t, J = 5.4 Hz,2H, H-4), 2.45-2.41/2.45-2.41 (m, 2H), 2.02/2.02 (t, J =7.2 Hz, 2H), 1.79-1.72/1.79-1.72 (m, 2H) ppm; 13C NMR(150 MHz, DMSO-d6): δ = 170.98/170.69, 168.96/168.96,135.92/135.83 (C-5a), 132.98/132.36 (C-4a), 125.29/125.03(C-9a), 120.66/120.63 (C-7), 118.53/118.50 (C-8),117.27/117.18 (C-9), 110.95/110.92 (C-6), 105.91/105.52(C-9b), 42.57/42.10 (C-3), 38.94/38.75 (C-1), 32.33/31.88,31.88/31.65, 23.79/22.89 (C-4), 21.01/20.86 ppm; HRMS(ESI): m/z calcd for [C16H19N3O3 + H]+302.1426, found302.1503.
 

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