Cyclohexane-1,3-dione | Ketones

CAS No. :	504-02-9
Formula :	C₆H₈O₂
M.W :	112.13
SMILES Code :	O=C1CC(CCC1)=O
MDL No. :	MFCD00001585
InChI Key :	HJSLFCCWAKVHIW-UHFFFAOYSA-N
Pubchem ID :	10434

Safety of [ 504-02-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H315-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of [ 504-02-9 ]

* 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 [ 504-02-9 ]

[ 504-02-9 ] Synthesis Path-Downstream 1~54

1
[ 50-00-0 ]
[ 98-55-5 ]
[ 504-02-9 ]
7-(1-Hydroxy-1-methyl-ethyl)-10a-methyl-2,3,4,5,6,7,8,8a,9,10a-decahydro-xanthen-1-one [ No CAS ]

References: [1]Heterocycles,1994,vol. 37,p. 661 - 666.

2
[ 122-31-6 ]
[ 504-02-9 ]
[ 53400-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate; In xylene; at 160℃; for 18h;	In a nitrogen atmosphere, 24 mL of malonaldehyde tetraethyl acetal and 7.71 g of ammonium acetate were added in that order to xylene (80 mL) solution of 11.2 g of 1,3-cyclohexadione, and a reflux condenser tube fitted with a Dean-Stark water separator was attached to the reactor, and this was stirred at 160C for 18 hours. The reaction liquid was cooled to room temperature, the solvent was evaporated off under reduced pressure, the residue was extracted with chloroform, and the chloroform layer was washed with saturated saline water and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (chloroform/methanol = 97/3) to obtain 2.21 g of the entitled compound.

References: [1]Synthetic Communications,1998,vol. 28,p. 1197 - 1200.
[2]Patent: EP1726590,2006,A1 .Location in patent: Page/Page column 35.

3
[ 504-02-9 ]
[ 111771-08-5 ]
2-fluoro-6-iodo-benzoic acid 3-oxo-cyclohex-1-enyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1999,vol. 40,p. 7595 - 7598.
[2]Tetrahedron,2003,vol. 59,p. 4237 - 4247.

4
[ 504-02-9 ]
[ 4637-24-5 ]
[ 51169-05-2 ]
1-pyridin-2-yl-1,5,6,7-tetrahydro-4H-indazol-4-one [ No CAS ]

References: [1]Synthesis,2002,p. 1669 - 1674.

5
[ 34595-26-1 ]
[ 504-02-9 ]
2',3',4',4a'-tetrahydro-1'H,6'H-spiro[cyclohexane-1,5'-pyrido[1,2-a]quinoline]-2,6-dione [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7109 - 7114.
[2]Russian Chemical Bulletin,2004,vol. 53,p. 1240 - 1247.

6
[ 504-02-9 ]
[ 4494-26-2 ]
[ 109-77-3 ]
5-(2-amino-3-cyano-5-oxo-5,6,7,8-tetrahydro-4H-chromen-4-yl)-1-(2-deoxypentofuranosyl)pyrimidine-2,4-(1H,3H)-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4052 - 4054.

7
[ 504-02-9 ]
aqueous hydrocyanic acid [ No CAS ]
[ 53400-41-2 ]

References: [1]Tetrahedron,2003,vol. 59,p. 8589 - 8595.
[2]Tetrahedron Letters,2002,vol. 43,p. 7929 - 7932.

8
[ 504-02-9 ]
[ 127724-75-8 ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 4194 - 4199.

9
[ 504-02-9 ]
[ 53400-41-2 ]

References: [1]Synthetic Communications,1998,vol. 28,p. 1197 - 1200.

10
[ 305381-67-3 ]
[ 504-02-9 ]
[ 305381-87-7 ]

Yield	Reaction Conditions	Operation in experiment
1.35 g (59%)	With 1,2-dichloro-ethane; triethylamine;	1.1 Cyclohexen-3-on-1-yl 1-methylbenzotriazole-5-carboxylate 1.5 g of 1-methylbenzotriazole-5-carboxylic acid (8.5 mmol) and 1.0g of 1,3-cyclohexanedione (8.9 mmol) were dissolved in 30 ml of abs. acetonitrile and admixed with 1.6 g of EDC (8.5 mmol), 2 ml of triethylamine and a cat. amount of DMAP. After the reaction had ended, the solution was poured into water and extracted with ethyl acetate. The organic phase was washed and dried and the product was then purified by crystallization. Yield: 1.35 g (59%). m.p.: 154-158 C.

References: [1]Patent: US6589915,2003,B1 .

11
[ 120100-15-4 ]
[ 504-02-9 ]
[ 247903-17-9 ]

Yield	Reaction Conditions	Operation in experiment
14.05 g (84%)		c) 3-(3-Carbomethoxy-2-chloroanilino)cyclohex-2-en-1-one A mixture of <strong>[120100-15-4]methyl 2-chloro-3-aminobenzoate</strong> (11.11 g, 59.86 mM) and 1,3-cyclohexanedione (9.05 g, 80.8 mM) was heated at 120 C. under a stream of nitrogen for 4 hours. The resultant solid was triturated with hot ethyl acetate, then dried in vacuo to afford 14.05 g (84%) of 3-(3-carbomethoxy-2-chloroanilino)cyclohex-2-en-1-one as a yellow orange solid. 1H NMR (CDCl3) delta 7.6 (dt, 1H, J=1 and 8 Hz), 7.3 (t, 1H, J=8 Hz), 6.6 (br s, 1H), 5.62 (s, 1H), 3.95 (s, 3H), 2.6 (t, 2H, J=6 Hz), 2.4 (t, 2H, J=6 Hz), and 2.1 (m, 2H). IR (CHCl3, cm-1) 3050, 2950, 1729, 1536, 1351, 1299, 1290, 1267, and 1135. MS (ES) m/e 278, 280, 282. Elemental Analyses for C14H14NO3Cl: Calculated: C, 60.11; H, 5.04; N, 5.01. Found: C, 57.51; H, 4.99; N, 4.68.

References: [1]Patent: US6177440,2001,B1 .

12
[ 675-10-5 ]
[ 667463-64-1 ]
[ 504-02-9 ]
[ 1206204-05-8 ]

References: [1]Organic Letters,2010,vol. 12,p. 572 - 575.

13
[ 504-02-9 ]
[ 156-87-6 ]
[ 53400-41-2 ]

References: [1]Synthetic Communications,2010,vol. 40,p. 1708 - 1716.

14
[ 2058-74-4 ]
[ 504-02-9 ]
[ 1194-22-5 ]
[ 1246222-53-6 ]