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Chemical Structure| 1072-87-3 Chemical Structure| 1072-87-3

Structure of Citraconimide
CAS No.: 1072-87-3

Chemical Structure| 1072-87-3

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Product Details of [ 1072-87-3 ]

CAS No. :1072-87-3
Formula : C5H5NO2
M.W : 111.10
SMILES Code : O=C(C(C)=C1)NC1=O
MDL No. :MFCD10699598
InChI Key :ZLPORNPZJNRGCO-UHFFFAOYSA-N
Pubchem ID :95941

Safety of [ 1072-87-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 1072-87-3 ]

* 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 [ 1072-87-3 ]

[ 1072-87-3 ] Synthesis Path-Downstream   1~54

  • 2
  • [ 6641-34-5 ]
  • [ 1072-87-3 ]
  • 3
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  • [ 1072-87-3 ]
  • 4
  • [ 7564-40-1 ]
  • [ 1072-87-3 ]
  • 5
  • [ 1072-87-3 ]
  • [ 51255-10-8 ]
YieldReaction ConditionsOperation in experiment
44% With sodium hypochlorite; sodium hydroxide; In water; at 0℃; for 4h;Inert atmosphere; To a mixture of NaOCl solution (4.99%, 10 mL) and NaOH (1.6 g, 40mmol) cooled at 0 C was added dropwise a precooled (0 C) solution of <strong>[1072-87-3]3-methylpyrrole-2,5-dione</strong> (3.55 g, 32 mmol) in H2O (14 mL). The reaction mixture was then stirred at the same temperature for 4 h to obtain a clear solution. After completion of reaction (monitored by TLC), dilute H2SO4 was added until pH 3 to form a white precipitate, which was filtered and dried to obtain the desired product as a white solid; yield: 1.8 g (44%); mp 115-117 C.IR (KBr): 2970, 2910, 2162, 1753, 1172, 813, 549 cm-1.1H NMR (400 MHz, DMSO-d6): δ = 1.67-1.87 (m, 3 H), 7.38-7.55 (m, 1H), 11.16-11.47 (m, 1 H).13C NMR (100 MHz, CDCl3): δ = 161.2, 148.9, 141.6, 103.1, 11.9.MS (ESI): m/z = 125.8 (M - H).
  • 6
  • [ 64-17-5 ]
  • [ 1072-87-3 ]
  • 3-methylsuccinimide [ No CAS ]
  • 5-Ethoxy-4-methyl-1,5-dihydro-pyrrol-2-one [ No CAS ]
  • 7
  • [ 1072-87-3 ]
  • [ 25561-30-2 ]
  • 3-Methyl-5-trimethylsilanyloxy-pyrrol-2-one [ No CAS ]
  • 8
  • [ 1072-87-3 ]
  • [ 870-85-9 ]
  • [ 80049-31-6 ]
  • 9
  • [ 1072-87-3 ]
  • [ 100-44-7 ]
  • [ 73383-82-1 ]
  • 10
  • [ 1072-87-3 ]
  • [ 35150-22-2 ]
  • [ 84165-67-3 ]
  • [ 84165-61-7 ]
  • 11
  • [ 1072-87-3 ]
  • [ 1099-45-2 ]
  • (Z)-5-ethoxycarbonylmethylene-1H-4-methylpyrrol-2(5H)-one [ No CAS ]
  • (E)-5-ethoxycarbonylmethylene-3-methyl-1H-pyrrol-2(5H)-one [ No CAS ]
  • (Z)-5-ethoxycarbonylmethylene-3-methyl-1H-pyrrol-2(5H)-one [ No CAS ]
  • 12
  • [ 1072-87-3 ]
  • 3-methylsuccinimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr; for 4h; To a solution of <strong>[1072-87-3]citraconimide</strong> (26) (4.50 g, 40.5 mmol) in ethanol (50 mL) 10% palladised charcoal (2.00 g) was added. The suspension was hydrogenated under atmospheric pressure for 4 h. After completion of the reaction (confirmed with TLC) the mixture was filtered through a pad of Celite, the Celite layer was washed with ethanol (2 _ 20 mL), and the filtrate was evaporated under reduced pressure, giving the title compound 27 as a white crystalline solid (4.55 g, 99%), mp 57-59 C (lit.: 65 C) [42]; Rf (DCM:MeOH 10:1) 0.52; nmax (KBr) 3201, 3071, 2766, 1763, 1707, 1352, 1206, 1176, 1037 cm_1; 1H NMR (400 MHz; DMSO-d6) d (ppm) 1.16 (3H; d; J 7.2 Hz; C(3)-CH3); 2.26 (1H; m; 2J_17.7 Hz (Ha-4), 3J 5.1Hz (H-3); Hb-4); 2.78 (1H; m; 3J 9.2 Hz (H-3); Ha-4); 2.81 (1H; m; 3J 7.3 Hz (C(3)-CH3); Ha-4); 10.94-11.10 (1H; br; NH-1); 13C NMR (101 MHz; DMSO-d6) d (ppm) 15.7 (C(3)-CH3); 35.4 (C-3); 37.1 (C-4); 178.0 (C-5); 182.2 (C-2); HRMS: M 113.0461 (delta _14.2 ppm; C5H7NO2); HR-EI-MS (rel. int. %): 113(100); 70(77).
With palladium on activated charcoal; hydrogen; All of the chemicals were commercially available, exceptfor racemic (5S)-2-methyl-5-(prop-1-en-2-yl) cyclohex-anone (P3), dimethyl 2-methylsuccinate (P15), methyl2-acetamidopropanoate (P16) and 3-methyl-2,5-Pyrrolidinedione(P30), which were obtained by Pd/C-catalyzed hydrogenation of (S)-carvone (S3), dimethyl itaconate (S15), methyl2-acetamidoacrylate (S16) and 3-methyl maleimide (S30),respectively [23].
  • 13
  • [ 1072-87-3 ]
  • 3-methylsuccinimide [ No CAS ]
  • 5-Ethoxy-4-methyl-1,5-dihydro-pyrrol-2-one [ No CAS ]
  • 15
  • [ 1072-87-3 ]
  • [ 69636-49-3 ]
  • 16
  • [ 616-02-4 ]
  • [ 1072-87-3 ]
YieldReaction ConditionsOperation in experiment
70% With 1,1,1,3,3,3-hexamethyl-disilazane; In N,N-dimethyl-formamide; at 100℃; for 1h; To a solution of citraconic anhydride (25) (12.0 g, 107 mmol) in DMF (100 mL) at 100 C hexamethyldisilazane (34.2 mL, 160 mmol) was added. The mixture was stirred at 100 C for 1 h, then it was cooled to room temperature. The solvent was evaporated under reduced pressure. The crude product was recrystallized from a mixture of hexane and ethyl acetate to give the title compound 26 as a white crystalline solid (8.33 g, 70%), mp 104-105 C (lit.: 104-105 C) [3]; Rf (DCM:MeOH 10:1) 0.71; nmax (KBr) 3271, 3098, 2674, 1844, 1778, 1764, 1712, 1634, 1342, 1284, 1175, 1090 cm_1; 1H NMR (500 MHz; DMSO-d6) d (ppm) 1.94 (3H; d; J 1.8 Hz; C(3)-CH3); 6.50 (1H; q; J 1.8 Hz; H-4); 10.72 (1H; br s; NH-1); 13C NMR (126 MHz; DMSO-d6) d (ppm) 10.2 (C(3)-CH3); 128.0 (C-4); 145.9 (C-3); 172.2 (C-5); 173.1 (C-2); HRMS: M 111.0311 (C5H5O2N; delta _8.1 ppm); HR-EI-MS (rel. int. %): 111(100); 83(8); 68(39).
40% With 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; N,N-dimethyl-formamide; at 0 - 20℃; for 20.3333h; Stage 1: 3-methylpyrrole-2,5-dione A solution of hexamethyldisilazane (80.7 g, 104.8 ml, 500 mmol) in methanol was added dropwise to a solution of citraconic anhydride (5.60 g, 4.49 ml, 50 mmol) in N,N-dimethylformamide (170 ml) at 0 C. The reaction solution was stirred at room temperature for 20 h, thereafter methanol (100 ml) was added and the mixture was stirred for a further 20 min. The solvent was concentrated in vacuo and the residue was taken up in a mixture of ethyl acetate/water (150 ml:50 ml). The organic phase was separated off, washed with water (2*50 ml), sodium bicarbonate solution (50 ml) and with water again (50 ml) and then dried with sodium sulfate. The solvent was concentrated and the residue was dried in vacuo. Yield: 2.30 g (40%), white solid Melting point: 100-102 C. [lit. 101-104 C. (K. R. Shah, C. DeWitt Blanton, J. Org. Chem. 1982, 47, 502)].
32% With urea; In sulfolane; at 180℃; for 1h;Product distribution / selectivity; 25 g (0.219 mol) of 2-methyl succinic anhydride were heated in 37.5 g of sulfolane to a reaction temperature of 180 C. After the reaction temperature was achieved 18.95 g (0.32 mol) of urea were spread in and stirring was continued for 1 h at the reaction temperature under flushing with N2. Following cooling, the reaction mixture was first added with 2-propanol and then with MTBE. 6.5 g of 2-methyl succinic imide (32% of the theoretical yield) were obtained
20% With urea; In diethyleneglycol diethylether; at 180℃;Product distribution / selectivity; EXAMPLE 25 In a manner analogous to that of Example 24, diethyleneglycol diethylether was used as the solvent at 180 C. After cooling, first MTBE was added. From the resulting oil 2-methyl succinic imide was obtained in a yield of 20% by recrystallization from ethanol.

  • 17
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  • [ 108-80-5 ]
  • 18
  • [ 2644-60-2 ]
  • [ 20189-42-8 ]
  • [ 14959-92-3 ]
  • [ 1072-87-3 ]
  • 19
  • [ 81971-99-5 ]
  • [ 14959-92-3 ]
  • [ 1072-87-3 ]
  • 20
  • [ 1072-87-3 ]
  • [ 197584-86-4 ]
  • (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methyl-pyrrolidine-2,5-dione [ No CAS ]
  • (3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methyl-pyrrolidine-2,5-dione [ No CAS ]
  • 21
  • [ 1072-87-3 ]
  • [ 37772-60-4 ]
YieldReaction ConditionsOperation in experiment
91% With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 - 0℃; for 1.5h;Inert atmosphere; To a solution of <strong>[1072-87-3]citraconimide</strong> (26) (1.00 g, 9.00 mmol) in THF (50 mL) under nitrogen at _78 C diisobutyl aluminium hydride solution (10.7 mL, 16.0 mmol, 25 wt % in toluene) was added via a syringe. The mixturewas let towarm up to 0 C and it was stirred at this temperature for a further 90 min, then it was quenched with a mixture of methanol (25 mL) and water (25 mL). The solvents were evaporated under reduced pressure, then the crude product was triturated in ethyl acetate. The suspension was filtered, the filtrate was dried (Na2SO4) and evaporated under reduced pressure to give the title compound 1 as a white crystalline solid (930 mg, 91%), mp 115-117 C (lit.: 115-118 C) [5]; Rf (DCM:MeOH 10:1) 0.42; nmax (KBr) 3244, 2985, 2931, 1688, 1650, 1409, 1306, 1281, 1216, 1058 cm_1; 1H NMR (500 MHz; CD3OD) d (ppm) 1.83 (3H; dd; J 1.7; 1.4 Hz; C(3)-CH3); 5.44 (1H; dq; 1.7; 1.4 Hz; H-5); 6.63 (1H; ~qui; J 1.7 Hz; H-4); 13C NMR (126 MHz; CD3OD) d (ppm) 10.6 (C(3)-CH3); 80.0 (C-5); 136.9 (C-3); 143.1 (C-4); 175.5 (C-2); HRMS: M+H 114.05495 (delta _0.04 ppm; C5H8O2N); HR-ESI-MS-MS (CID 55%, rel. int. %): 97(100).
  • 24
  • Boscan 9K3 crude oil (Cretaceous, W.Venezuela) of fraction 2 [ No CAS ]
  • [ 1072-87-3 ]
  • 25
  • [ 37772-60-4 ]
  • [ 1072-87-3 ]
  • [ 50656-76-3 ]
  • 26
  • [ 1072-87-3 ]
  • [ 165606-93-9 ]
  • 3-chloro-4-dichloromethyl-pyrrole-2,5-dione [ No CAS ]
  • 27
  • [ 26608-34-4 ]
  • [ 17825-86-4 ]
  • [ 20189-42-8 ]
  • [ 1072-87-3 ]
  • 28
  • [ 106897-01-2 ]
  • [ 1072-87-3 ]
  • [ 840544-12-9 ]
  • 29
  • [ 1072-87-3 ]
  • [ 53598-99-5 ]
  • 30
  • [ 1072-87-3 ]
  • (5Z)-1,5-dihydro-4-methyl-5-(2-methylpropylidene)pyrrol-2(2H)-one [ No CAS ]
  • 31
  • [ 1072-87-3 ]
  • [ 443680-34-0 ]
  • 32
  • [ 1072-87-3 ]
  • [ 752222-91-6 ]
  • 33
  • [ 1072-87-3 ]
  • [ 171017-20-2 ]
  • 34
  • [ 1072-87-3 ]
  • (5E)-1,5-dihydro-4-methyl-5-(2-methylpropylidene)pyrrol-2(2H)-one [ No CAS ]
  • 35
  • [ 1072-87-3 ]
  • [ 443680-35-1 ]
  • 36
  • [ 1072-87-3 ]
  • 1,5-dihydro-3-methyl-5-(2-methylpropylidene)pyrrol-2(2H)-one [ No CAS ]
  • 37
  • [ 1072-87-3 ]
  • 5-(1-hydroxy-2-methyl-propyl)-3-methyl-2-oxo-2,5-dihydro-pyrrole-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 38
  • [ 1072-87-3 ]
  • [ 50656-76-3 ]
  • 39
  • [ 1072-87-3 ]
  • [ 128866-07-9 ]
  • 40
  • [ 1072-87-3 ]
  • [ 150254-84-5 ]
  • 41
  • [ 1072-87-3 ]
  • [ 150254-86-7 ]
  • 42
  • [ 1072-87-3 ]
  • (+/-)-N-(4-Aminobutyl)-3-methylsuccinimide hydrochloride [ No CAS ]
  • 43
  • [ 1072-87-3 ]
  • [ 69636-50-6 ]
  • 44
  • [ 1072-87-3 ]
  • [ 80049-32-7 ]
  • 45
  • [ 1072-87-3 ]
  • [ 4403-69-4 ]
  • [ 940055-61-8 ]
YieldReaction ConditionsOperation in experiment
37% In ethyl acetate; at 50℃; for 48h; Stage 2: 3-(2-aminobenzylamino)-3-methylpyrrolidine-2,5-dione A solution of the product from stage 1 (1.94 g, 17.5 mmol) and 2-aminobenzylamine (1.49 g, 12.2 mmol) in ethyl acetate (44 ml) was stirred at 50 C. for 48 h and thereafter concentrated in vacuo. The residue (3.8 g) was fractionated by flash chromatography with chloroform/methanol (9:1). Yield: 1.07 g (37%), white solid. Melting point: 129-134 C.
  • 46
  • [ 1072-87-3 ]
  • [ 117307-07-0 ]
YieldReaction ConditionsOperation in experiment
With ene reductase from the cyanobacterium synechococcus species pcc 7942; NAD; In N,N-dimethyl-formamide; at 30℃; for 24h;pH 7.0;Enzymatic reaction; The bioreduction of alkenes was carried out in 1 mL sodium phosphate buffer (100 mM, pH 7.0) containing 5 mM substrates (added as a DMF solution, mM NADH and 85 μg mL-1 (2.1 μM) Syn7942ER. The reactions were agitated at 30 C and 300 rpm (Thermomixer comfort, Eppendorf, Hamburg, Germany) for 24 h. The reduction of ketoisophorone with 5-20% (v/v) ethanol, iso-propanol or DMF was performed on a 1 mL-scale with 57 μg mL-1 (1.2 μM) NADP+-dependent MycFDH C145S/D221Q/C255V [37], 250 mM sodium formate, 0.5 mM NADP+, 10 mM ketoisophorone and 25 μg mL-1 (0.6 μM) Syn7942ER for 6 h at 30 C and 150 rpm (WiseCube, Witeg Labortechnik, Wertheim, Germany). Reactions were stopped by extraction with ethyl acetate (1:1) containing 36 mM (R)-limonene as internal standard.
With D-glucose; D-glucose dehydrogenase; Bacillus Old Yellow Enzyme 1, molecular mass: ca. 41 kDa; NADP; In aq. buffer; at 30℃; for 24h;pH 8.0;Enzymatic reaction; General procedure: The bioconversion reactions for substrates S2, S3, S15, S16, S24 and S30 were performed in 1 mL of Tris-HCl buffer (50 mM, pH8.0). The reaction system contained d-glucose (11 g L-1), d-glucose dehydrogenase (1.5 g L-1), NADP+ (1 g L-1), OYE (2 g L-1) and substrate (20 mM). The mixtures were incubated at 30 C, 200 rpm for 24 h and then extracted with an equal volume of ethyl acetate. The conversions and enantiomeric excess (ee)/diasteromeric excess(de) values of the reactions were measured by chiral GC analysis on an Agilent 7890 gas chromatography using CP ChiraSilDEX Column (25 m × 0.25 mm × 0.25 m, Varian, USA) for S2,S3, S16 and S24, and Gamma DEXTM 225 Capillary Column(30 m × 0.25 mm × 0.25 m, SUPELCO, Japan) for S15 and S30. Temperature programs were as follows: For S2: 10C min-1from 70to 100C, 100C for 10 min, 5C min-1to 120C, 60C min-1to180C, 180C for 3 min. For S3: 10C min-1from 70 to 100C,100C for 14 min, 60C min-1to 180C, 180C for 3 min. For S24:70C for 2 min, 5C min-1from 70 to 140C, 140C for 3 min,50C min-1to 180C, 180C for 3 min. For S16: 95C for 10 min,40C min-1from 95 to 160C, 160C for 3 min. For S15: 10C min-1from 70 to 100C, 100C for 7.2 min, 60C min-1to 180C, 180Cfor 3 min. For S30: 10C min-1from 80 to known enzymes, YqjM and morphinone reductase, which were performed at the same time [5,25,26]. For other substrates, the product configuration was determined as previously reported [16,27].170C, 170C for 15 min,10C min-1to 180C, 180C for 3 min. In order to determine the product configuration, the GC data were compared with those ofthe reduction products of S15, S16 and S30 catalyzed by known enzymes, YqjM and morphinone reductase, which were performedat the same time [5,25,26]. For other substrates, the product con-figuration was determined as previously reported [16,27].
  • 48
  • [ 5522-66-7 ]
  • [ 17825-86-4 ]
  • [ 20189-42-8 ]
  • [ 136918-14-4 ]
  • [ 16493-21-3 ]
  • [ 7251-82-3 ]
  • [ 70556-92-2 ]
  • [ 5997-62-6 ]
  • [ 1072-87-3 ]
  • 2-methoxycarbonylethyl-3-methylMi [ No CAS ]
  • 2-methyl-3-(n-pentyl)Mi [ No CAS ]
  • 49
  • [ 1072-87-3 ]
  • [1-(methoxymethyl)-4-methyl-5-oxo-2H-pyrrol-2-yl] N-benzylcarbamate [ No CAS ]
  • 50
  • [ 1072-87-3 ]
  • 2-hydroxy-1-(methoxymethyl)-4-methyl-2 H-pyrrol-5-one [ No CAS ]
  • 51
  • [ 109-87-5 ]
  • [ 1072-87-3 ]
  • 1-(methoxymethyl)-3-methyl-pyrrole-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With tin(IV) chloride; at 40℃; for 5h;Inert atmosphere; To a solution of <strong>[1072-87-3]3-methylpyrrole-2,5-dione</strong> (4.50 mmol, 0.500 g, as prepared inEuropean Journal of Organic Chemistry 2008,9, 1511-1516) in dimethoxymethane (20 mL)under nitrogen was added slowly tin(IV) chloride (5.40 mmol, 0.632 mL) . The reaction mixturewas heated to 40 C for 5 h and then cooled down to room temperature. The reaction mixturewas then carefully neutralized with a saturated solution of potassium carbonate and extractedwith ethyl acetate (3 x 20 mL). The organic phase was dried and evaporated giving the title compound as a white solid (657 mg, 94%). 1H NMR (400 MHz, ODd3) 3: 6.44 (1 H, s), 4.89 (2 H, s), 3.35 (3 H, s), 2.13 (3 H, s).
94% With tin(IV) chloride; at 40℃; for 5h;Inert atmosphere; Step 1: Preparation of 1-(methoxymethyl)-3-methyl-pyrrole-2,5-dione (compound Vl-1) To a solution of <strong>[1072-87-3]3-methylpyrrole-2,5-dione</strong> (4.50 mmol, 0.500 g, as prepared in European Journal of Organic Chemistry (2008), 9, 1511-1516) in dimethoxymethane (20 mL) under nitrogen was added slowly tin(IV) chloride (5.40 mmol, 0.632 mL) . The reaction mixturewas heated to 40 00 for 5 hours (h) and then cooled down to room temperature. The reaction mixture was then carefully neutralized with a saturated solution of potassium carbonate and extracted with ethyl acetate (3x20 mL). The organic phase was dried and evaporated giving 1- (methoxymethyl)-3-methyl-pyrrole-2,5-dione (compound Vl-1) as a white solid (657 mg, 94%). 1H NMR (400 MHz, CDCI3): (ppm) 6.44 (1 H, s), 4.89 (2 H, s), 3.35 (3 H, s), 2.13 (3 H, s).
  • 52
  • [ 1072-87-3 ]
  • 2-chloro-1-(methoxymethyl)-4-methyl-2H-pyrrol-5-one [ No CAS ]
  • 53
  • [ 1072-87-3 ]
  • tert-butyl (3E)-3-[[1-(methoxymethyl)-4-methyl-5-oxo-2H-pyrrol-2-yl]oxymethylene]-2-oxo-4,8b-dihydro-3aH-indeno[1,2-b]pyrrole-1-carboxylate [ No CAS ]
  • 54
  • [ 1072-87-3 ]
  • (3E)-3-[[1-(methoxymethyl)-4-methyl-5-oxo-2H-pyrrol-2-yl]oxymethylene]-1,3a,4,8b-tetrahydroindeno[1,2-b]pyrrol-2-one [ No CAS ]
 

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Technical Information

Categories

Related Parent Nucleus of
[ 1072-87-3 ]

Pyrroles

Chemical Structure| 1823773-11-0

A390889 [1823773-11-0]

3,3'-(Ethane-1,2-diyl)bis(1H-pyrrole-2,5-dione)

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