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[ CAS No. 116-53-0 ]

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2D
Chemical Structure| 116-53-0
Chemical Structure| 116-53-0
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Product Details of [ 116-53-0 ]

CAS No. :116-53-0MDL No. :MFCD00002669
Formula :C5H10O2Boiling Point :176-177°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :102.13Pubchem ID :-
Synonyms :

Computed Properties of [ 116-53-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 116-53-0 ]

Signal Word:DangerClass8
Precautionary Statements:P280-P305 P351 P338-P310UN#:3265
Hazard Statements:H227-H302 H312-H314Packing Group:
GHS Pictogram:

Application In Synthesis of [ 116-53-0 ]

  • Downstream synthetic route of [ 116-53-0 ]

[ 116-53-0 ] Synthesis Path-Downstream   1~10

  • 2
  • [ 116-53-0 ]
  • [ 5856-79-1 ]
YieldReaction ConditionsOperation in experiment
83% With thionyl chloride; for 2h;Reflux; A dry solution of (±)-2-methylbutyric acid (5 mL, 46 mmol) and thionyl chloride (8mL, 110 mmol) was refluxed for 2 h, after which the mixture was cooled and the excessthionyl chloride removed by distillation to yield (±)-2-methylbutyryl chloride (4.7 g, 83%),which was used immediately without further purification. Adenine (75 mg, 0.55 mmol) in drypyridine (5 mL) was treated with (±)-2-methylbutyryl chloride (100 muL, 0.81 mmol) andrefluxed for 16 h, after which the pyridine was removed by vacuum distillation and theresidue neutralised with 2M aq Na2CO3, triturated with MeOH (15 mL) and concentrated invacuo to yield a crude reaction product (86 mg). C18 SPE fractionation (33% stepwisegradient elution from 66% H2O/MeOH to 100% MeOH) afforded rac-phorioadenine A as awhite solid that was spectroscopically (UV, NMR, MS) identical to 1. 13C NMR (100 MHz,CD3OD) deltaC: 12.0 (C-4?), 17.6 (2?-CH3), 28.2 (C-3?), 43.6 (C-2?), 115.0 (C-5), 146.1 (C-8),146.3 (C-6), 153.0 (C-2), 161.8 (C-4), 178.8 (C-1?).
With thionyl chloride; The free carboxylic acids produced were chlorinated with thionyl chloride. The obtained acylchloride (9 mmol) was dissolved in 20 ml dry acetone and was added dropwise to stirred solution of suitable sulfonamide derivative (9.2mmol) and pyridine (9.1 mmol) in 50ml dry acetone. After addition, the reaction mixture was stirred for 12h at room temperature. The organic solvent was then evaporated under vacuum and the residue dissolved in 100ml ethyl acetate and washed three times with 20ml of distilled water. 10% HC1 solution was added until pH=l was reached and the organic phase was separated from the aqueous phase and washed three times with brine. The aqueous phase was combined and extracted with ethyl acetate (3 X 50 ml). The ethyl acetate extracts were combined, dried over MgS04, filtered and evaporated.The obtained products were purified by crystallization using ethanol/petroleum ether mixture (1:3).
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 3h; Step 1:To a solution of 2-methyl-butyric acid (40 g, 392 mmol) and DMF (2 drops, 0.1 mL) in CH2Cl2 (100 mL) at 0 C. was added oxalyl chloride (54.7 mL, 627 mmol, 1.6 equiv.) dropwise. The reaction was stirred at 0 C. for 1 h and then room temperature for 2 h. The reaction mixture was concentrated under reduced pressure with a rotary evaporator (bath temperature <20 C.). Dry CH2Cl2 was added and evaporated. The process was repeated three times to remove residual oxalyl chloride. The desired acid chloride 2-1 was collected as a yellow oil (38 g) in the bump trap after raising the bath temperature to 40 C. The product was used in the next step without further purification.
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[4]Liebigs Annalen der Chemie,1988,p. 877 - 880
[5]Helvetica Chimica Acta,1982,vol. 65,p. 13 - 25
[6]Journal of Chemical Research, Miniprint,1990,p. 440 - 472
[7]Journal of Medicinal Chemistry,2012,vol. 55,p. 1056 - 1071
[8]Chemische Berichte,1937,vol. 70,p. 1042
[9]Journal of the American Chemical Society,1940,vol. 62,p. 2459
    Journal of the American Chemical Society,1941,vol. 63,p. 3161
[10]Tetrahedron,1970,vol. 26,p. 3619 - 3629
[11]Tetrahedron,1988,vol. 44,p. 3501 - 3512
[12]Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry,1982,vol. 36,p. 467 - 474
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[14]Synthesis,2002,p. 1391 - 1397
[15]Journal of Organic Chemistry,2000,vol. 65,p. 397 - 404
[16]Journal of Organic Chemistry,2002,vol. 67,p. 8938 - 8942
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[18]Helvetica Chimica Acta,2010,vol. 93,p. 290 - 297
[19]Journal of Medicinal Chemistry,2010,vol. 53,p. 4177 - 4186
[20]Patent: WO2011/33518,2011,A1.Location in patent: Page/Page column 27
[21]Patent: US2011/71179,2011,A1.Location in patent: Page/Page column 18
[22]Journal of Ethnopharmacology,2010,vol. 131,p. 425 - 432
[23]Canadian Journal of Chemistry,2013,vol. 91,p. 1 - 5
[24]Journal of the American Chemical Society,2015,vol. 137,p. 3338 - 3351
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  • 3
  • [ 116-53-0 ]
  • [ 574-66-3 ]
  • (±)-diphenylmethanone O-(2-methylbutanoyl) oxime [ No CAS ]
  • 4
  • [ 80-59-1 ]
  • [ 116-53-0 ]
  • C5H4(2)H4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 5%-palladium/activated carbon; water-d2; deuterium; benzylamine; Cinchonidin; In 1,4-dioxane; at 23℃; under 750.075 Torr; for 3h; Deuteration of 1 was similarly carried out using D2 and D2Oinstead of H2 and H2O. Typically, 40 mg of Pd/C, 6mg (0.02mmol) of CD, and benzylamine (0.5mmol) were used for thereaction of 0.5mmol of 1 in 10mL of the solvent. The deuteratedproduct 3 obtained was analyzed by 1HNMR (JEOL ECA-600) and ESI-MS (JEOL JMS-T100LC). GC-MS was performedusing a Shimadzu GCMS-QP 2010 equipped with theDEX-CB column. The 1HNMR signals of 3 were assignedaccording to previous reports
  • 5
  • [ 80-59-1 ]
  • [ 116-53-0 ]
  • C5H8(2)H2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 5%-palladium/activated carbon; hydrogen; water-d2; benzylamine; Cinchonidin; In 1,4-dioxane; at 23℃; under 750.075 Torr; Deuteration of 1 was similarly carried out using D2 and D2Oinstead of H2 and H2O. Typically, 40 mg of Pd/C, 6mg (0.02mmol) of CD, and benzylamine (0.5mmol) were used for thereaction of 0.5mmol of 1 in 10mL of the solvent. The deuteratedproduct 3 obtained was analyzed by 1HNMR (JEOL ECA-600) and ESI-MS (JEOL JMS-T100LC). GC-MS was performedusing a Shimadzu GCMS-QP 2010 equipped with theDEX-CB column. The 1HNMR signals of 3 were assignedaccording to previous reports
  • 6
  • [ 116-53-0 ]
  • [ 524-38-9 ]
  • 1,3-dioxoisoindolin-2-yl 2-methylbutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 5 - 10h; General procedure: The corresponding carboxylic acids (10 mmol, 1 equiv), N-hydroxyphthalimide (11 mmol, 1.1 equiv), and 4-dimethylaminopyridine (0.1 mmol, 10 mol%) were mixed in a flask with a magnetic stirring bar, 30 mL CH2Cl2 was added. Then a solution of N, N-dicyclohexylcarbodiimide (11 mmol, 1.1 equiv) in CH2Cl2 (10 mL) was added slowly at room temperature. The reaction mixture was maintained at room temperature with stirring for 5-10h. The white precipitate was filtered off and the solution was concentrated on a rotary evaporator. The residue was purified by flash column chromatography to give corresponding redox active esters.
  • 7
  • [ 116-53-0 ]
  • [ 1071-46-1 ]
  • [ 98192-72-4 ]
YieldReaction ConditionsOperation in experiment
71% To a solution of 3-ethoxy-3-oxopropanoic acid (6.47 g, 49.0 mmol) in THF (20 mL) at OeC was added dropwise isopropylmagnesium chloride solution (2M in THF, 47.3 mL, 95 mmol) and the reaction mixture was stirred for 5 h at 20eC. Thereafter, this solution was cooled to OeC and then added dropwise to a THF (25 mL) solution tin of [116-53-0]2-methylbutanoic acid (5.34 mL, 49.0 mmol) and Cdi (6.35 g, 39.2 mmol) which was preformed after stirring at room temperature for 12 h. The combined reaction mixture was stirred for 2 h at room temperature. Upon completion, the reaction mixture was quenched with 10% aqueous citric acid (25 mL), extracted with EtOAc, washed with aqueous saturated NaHC03, dried over Na2S04, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel using hexane/ ethyl acetate (5:95) to afford desired product (4 g, 71% yield). 1HNMR (400 MHz, DMSO-d6) U4.10 (q, J = 7.0 Hz, 2H), 3.64 (s, 2H), 2.63 ' 2.52 (m, 1H), 1.70 -1.54 (m, 1H), 1.43 ' 1.29 (m, 1H), 1.19 (t, J = 7.1Hz, 3H), 1.01 (d, J = 6.9 Hz, 3H), 0.83 (t, J = 7.5 Hz, 3H); GCMS (m/z) 172.2(M)+.
  • 8
  • [ 922-63-4 ]
  • [ 116-53-0 ]
YieldReaction ConditionsOperation in experiment
92% With palladium 10% on activated carbon; hydrogen; acetone; at 30℃; under 760.051 Torr;Autoclave; Industrial scale; In a 100 L autoclave were sequentially added 16.8 kg of 2-ethyl acrolein, 168 g of 10% palladium carbon, 30 kg of acetone,The reaction was replaced with nitrogen, and then three times with hydrogen,Then close the pressure relief valve, open the hydrogen inlet valve,Inflate to 1 atmosphere. Then heated to 30 C ± 2 C ,And this temperature insulation reaction,Until the reaction is no longer absorbed hydrogen,This process takes about 1.5 hours. TLC and GC detection reaction is completed, the reaction solution was filtered to recover palladium carbon catalyst, the filtrate was added 13.2 grams of sodium tungstate, the reaction temperature was controlled at 40 C ± 2 C ,Slowly drop 25% hydrogen peroxide 27.8 kg,After TLC and GC detection of the reaction was complete, sodium tungstate was filtered off,The reaction mixture was distilled to give a crude product of 99.0% purity,After the distillation column distillation separation of the desired product 2-methylButyric acid 18.8 kg, GC content 99.8%, yield 92%.
Step S1, the raw material 2-ethyl acrolein and acetone solvent Stir the reaction kettle, adding 2-ethyl acrolein 15% by weight of a solid catalyst,After purging with nitrogen, hydrogen gas was introduced into the reactor at 0.15 MPa and reacted at 50 C. for 6 hours; the added weight of acetone was 4 times the weight of 2-ethyl acrolein;Step S2, dropping a mass fraction of 26% hydrogen peroxide solution into the solution obtained in Step S1 at a temperature of 40 C., and then keeping the reaction at this temperature for 4 hours; the mole number of H2O2 is 1.2 of the mole number of 2-ethyl acrolein TimesStep S3, the reaction solution obtained in step S2 filtered to remove solid catalyst, the filtrate was distilled to give the desired product 2-methyl butyric acid. The preparation method of the solid catalyst comprises:Step S1, dissolving AlCl3 with deionized water, adding glycerin, stirring evenly,Ammonia water to adjust the pH value of the white precipitate, filtered, washed, wet cake; step S2,Zr (NO3) 4 · 5H2O is dissolved in a hydrochloric acid solution with a mass fraction of 20%; step S3,The wet cake was stirred and dissolved in the solution obtained in Step S2 to obtain a mixed solution, and the mixed solution was evaporated to obtain a white solid. The white solid was mixed and ground with the modified nano zeolite powder in a weight ratio of 1: 2.5,Then calcined in a muffle furnace at 600 C for 4 hours to obtain the solid catalyst.Among them, glycerin added weight of AlCl3 added to 3% by weight;AlCl3 and Zr (NO3) 4 · 5H2O molar ratio of 1: 2,The molar ratio of AlCl3 and Zr (NO3) 4 · 5H2O to the molar amount of HCl is 1: 3.The modified nano zeolite powder preparation method is: take nano zeolite powder 35 parts dispersed in 55 parts by mass of 10%Of ethylenediaminetetraacetic acid disodium aqueous solution was stirred at 45 C for 1.5 hours, then added 10 parts of nickel sulfate,Stir 25min, after cooling filtration, drying that.
  • 9
  • [ 116-53-0 ]
  • [ 59434-20-7 ]
  • 2-methyl-1-(2,4,6-tris(benzyloxy)phenyl)butan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% A mixture of trifluoroacetic anhydride (2.42 mL, 17.2 mmol) and (+-)-2-methylbutyric acid (1.60 mL, 14.4 mmol) was vigorously stirred for 2 h at room temperature. The yellow mixture was cooled in an ice bath to 0 C and a solution of tribenzyl phloroglucinol 14 (0.7 g, 1.77 mmol) in CH2Cl2 (25 mL) was added dropwise. The solution was stirred at room temperature for 1 h, then saturated aqueous NaHCO3 (20 mL) was added. The phases were separated and the aqueous layer was extracted with AcOEt. The combined organic layers were dried over MgSO4, filtered and the solvent removed under reduced pressure. The oily residue was purified by column chromatography (SiO2; hexanes/diethyl ether 9:1) to afford 15 (604 mg, 71%) as a white solid. Mp 72-73 C. 1H NMR (500 MHz, CDCl3) delta 7.34 (m, 15H), 6.25 (s, 2H), 5.02 (s, 4H), 5.00 (s, 2H), 2.95 (m, 1H), 1.77 (m, 1H), 1.36 (m, 1H), 1.07 (d, J = 7.0 Hz, 3H), 0.80 (t, J = 7.4 Hz, 3H); 13C NMR (125 MHz, CDCl3) delta 208.0 (CO), 161.0 (C), 157.3 (2C), 136.6 (2C), 136.5 (C), 128.8 (2CH), 128.6 (4CH), 128.3 (CH), 128.0 (2CH), 127.7 (2CH), 127.3 (4CH), 114.9 (C), 93.4 (2CH), 70.6 (2CH2), 70.4 (CH2), 49.1 (CH), 25.4 (CH2), 15.2 (CH3), 11.7 (CH3); EIMS m/z 480 (M+, 1), 423 (62), 91 (100); HREIMS (EI) 480.2293 (calcd for C32H32O4; [M+] 480.2301); IR (film) numax 3032, 2965, 2930, 2873, 1693, 1602, 1497, 1454, 1431, 1376, 1203, 1152, 1117 cm-1.
  • 10
  • [ 1679-47-6 ]
  • [ 116-53-0 ]
YieldReaction ConditionsOperation in experiment
33% With palladium 10% on activated carbon; W(OTf)6; hydrogen; at 180℃; under 760.051 Torr; for 12h; Specific methods are as follows: propiolactone was added (0.36g, 5mmol), palladium on carbon (10%, 26.5mg, 0.025mmol, 0.5mol%) in the reactor and W (OTf)6(107.8mg, 0.1mmol, 2mol%). A hydrogen balloon connected to the top of the reactor, and the reactor was purged with hydrogen gas atmosphere. Hydrogen atmosphere at normal pressure, the reaction was stirred at 135 deg.] C after 12h, detected by gas, gamma- valerolactone complete conversion of starting material, and only n-valeric acid. The method carried out as follows completion of the hydrogenation reaction of the ring-opening reaction system separation, to obtain the desired product n-valeric acid: The reaction was completed reaction mixture was dissolved with methylene chloride, filtered to remove the palladium on carbon catalyst and W (OTf)699% yield measured propionic acid, purity of the product was 99%. NMR data for the product using the embodiment of the present invention is the NMR identified the product as follows:The specific reaction procedure and operation method were the same as in Example 27 except that the reaction temperature was changed to 180 C, the yield 33%, the purity of the product is 99%. The product was subjected to nuclear magnetic identification using the manner described in the present invention, and the NMR data of the product were as follows:
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