873-95-0|3-Amino-5,5-dimethylcyclohex-2-enone| Ambeed

Structure of 873-95-0

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size

Price

VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock

{[ item.pr_size ]}

Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

Quality Control of [ 873-95-0 ] Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 873-95-0 ]

CAS No. :	873-95-0
Formula :	C₈H₁₃NO
M.W :	139.19
SMILES Code :	NC(CC(C)(C)C1)=CC1=O
MDL No. :	MFCD00045531
InChI Key :	MTZNODTZOSBYJW-UHFFFAOYSA-N
Pubchem ID :	136680

Safety of [ 873-95-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 873-95-0 ]

* 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 [ 873-95-0 ]

[ 873-95-0 ] Synthesis Path-Downstream 1~54

1
[ 126-81-8 ]
[ 873-95-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With ammonium acetate; In acetic acid; benzene; for 1h;Reflux;	Preparation 13-Bromo-7,7-dimethyl-7,8-dihydroquinolin-5(6H)-one[00143]A mixture of 5,5-dimethylcyclohexane-1 ,3-dione (1 1 .21 g, 80 mmol), ammonium acetate (12.33 g, 160 mmol), glacial acetic acid (1 mL), and benzene (150 mL) is stirred at reflux with a Dean-Stark trap for 1 h, cooled down to r.t., poured into saturated aqueous sodium bicarbonate solution, and extracted twice with EtOAc. The combined organic phases are washed with water, dried over sodium sulfate, concentrated at reduced pressure, and dried in vacuum to give 3-amino-5,5-dimethylcyclohex-2-enone (10.37 g, 93%) as yellow solid.
90%	With ammonium acetate; In toluene; for 2h;Molecular sieve; Reflux;	A mixture of 0.28 g dimedone (2 mmol) and 0.23 g ammonium acetate (3 mmol) in 5 cm3 dry toluene in the presence of 4 A molecular sieves was refluxed for 2 h. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to room temperature and the precipitate was filtered and then purified by recrystallization from dry toluene. 3-Amino-5,5-dimethyl-2-cyclohexen-1-one (3) was obtained as needles (0.25 g,90 %). M.p.: 163-165 C (Ref. [50] 163.5-164 C).
90%	With ammonium acetate; In water; at 80℃; for 5h;	A mixture of dimedone (1) (1.0 g, 7.1 mmol) and NH4OAc (1.32 g, 21.4 mmol) was heated in30 mL of water at 80 C for 5 hours. After the TLC indicated the consumption of dimedone(2), the reaction mixture was extracted with ethyl acetate several times. The combinedorganic layer was dried over sodium sulphate and evaporated to provide enaminone (2) (0.9g, 90%) as light yellow solid.

86%	With ammonium acetate; acetic acid; In toluene; for 5h;Reflux; Dean-Stark;	3-Amino-5,5-dimethyl-2-cyclohexen-1 -one 3-Amino-5,5-dimethyl-2-cyclohexen-1 -one can be synthesized as known from literature or can be obtained by the following synthesis: A mixture of 200 g dimedone, 143 g ammonium acetate, and 5 ml acetic acid in 2 L toluene is refluxed for 5 h at a Dean-Stark trap. Then the solution is cooled to room temperature and stirred for 16 h. The suspension is filtered and the filter cake is dried at 65C. Yield: 171 g (86 % of theory) Mass spectrometry (ESI+): m/z = 140 [M+H]+ Rf-value: 0.31 (silica gel, dichloromethane/ethanol 9:1 )
86%	With ammonium acetate; In acetic acid; toluene; at 20℃; for 21h;Reflux; Dean-Stark;	3-Amino-5,5-dimethyl-2-cyclohexen-1-one can be synthesized as known from literature or can be obtained by the following synthesis: [0223] A mixture of 200 g dimedone, 143 g ammonium acetate, and 5 ml acetic acid in 2 L toluene is refluxed for 5 h at a Dean-Stark trap. Then the solution is cooled to room temperature and stirred for 16 h. The suspension is filtered and the filter cake is dried at 65 C. [0224] Yield: 171 g (86% of theory) [0225] Mass spectrometry (ESI+): m/z=140 [M+H]+ [0226] Rf-value: 0.31 (silica gel, dichloromethane/ethanol 9:1)
85%	With ammonium acetate; In toluene; for 5h;Reflux;	5,5-dimethylcyclohexane-1,3-dione 10 (7.0 g,50 mmol) was added to a mixture of ammonium acetate (3.85 g, 50 mmol) in dry toluene(100 mL). The mixture was heated for 5 h under reflux using a Dean-Stark water separator.The red oily layer formed was then separated and recrystallized with ethyl acetate to afford3-amino-5,5-dimethylcyclohex-2-enone 11 (5.9 g, yield 85%) as a yellow solid. 1H-NMR (300 MHz,DMSO-d6)δ 6.67 (s, 2H), 4.90 (s, 1H), 2.11 (s, 2H), 1.90 (s, 2H), 0.96 (s, 6H).
	With ammonium acetate; acetic acid; In benzene; for 5h;Reflux;	The title compound was prepared in a similar manner as described by P.G. Baraldi, Synthetic Communications, 1983, 902. To a suspension of 5,5-dimethylcyclohexane-1,3-dione (10 g, 71 .3 mmol) in benzene (180 mL) were added acetic acid (1.84 mL, 31.2 mmol) and ammonium acetate (11.0 g, 143 mmol). The reaction mixture was refluxed for 5 h and the water formed was removed azeotropically using a Dean-Stark apparatus. Subsequently the reaction mixture was cooled to RT, quenched with sat. aq. Na2CO3 and iN aq. NaOH and extracted with CH2CI2 several times. The combined organic extracts were dried (Na2504), filtered and concentrated to afford the title compound. MS (UPLCMS): 139.9 [M+H]+; tR (HPLC conditions i): 0.48 mm
	With ammonium acetate; In toluene; for 3h;Reflux; Dean-Stark;	General procedure: 10 mmol cyclic 1,3-diketone wasadded to a mixture of 10 mmol ammonium acetate in dry toluene (20 mL). Themixture was heated for 3 h under reux using a Dean-Stark water separator. Theresulting oily product was separated and recrystallized with ethylacetate to give the corresponding enaminone as crystals. The enaminone productwas dissolved in 50ml THF and 2 equiv. of pyridine were added. To the mixedsolution, acetyl chloride (2 equiv.) in 5ml THF was added dropwise at 0 C. Thereaction mixture was warmed up to ambient temperature and stirred additional 5h at 60oC. The solvent was removed undervacuum and the crude product purified by flash chromatography
	With ammonium acetate; In neat (no solvent); at 90℃; for 0.5h;Green chemistry;	General procedure: The SBA-IL (0.02 g) was activated in vacuum at 100 C and then after cooling to room temperature, dimedone 7 (1.5 mmol) and ammonium acetate 8 (2.4 mmol) were added to it. In solvent-free conditions, the whole reaction mixture was heated at 90 C for 30 min. After completion of the first step and without any work-up, Meldrum’s acid 10 (1.5 mmol) and aldehyde 11a-i (1.5 mmol) were added to the reaction mixture, as reported in Table 2, at 90 C. The completion of two steps of the reaction was indicated by TLC, the resulting solid product was dissolved in hot ethanol, filtered to remove the unsolvable catalyst, and the filtrate was cooled to afford the pure product. The spectroscopic and analytical data for new compounds are presented in the following section.
		General procedure: A mixture of dimedone or cyclohexane-1,3-dione (1 mmol), ammonium acetate(1.5 mmol) was heated at 100 C for appropriate time. After completion of the reactionindicated by TLC (1-2 h), the reaction mixture was cooled to room temperature.By addition of a few drops of chloroform, the yellow precipitate was obtained, whichwas purified by recrystallization from n-hexane/ethyl acetate, m. p. = 157-159 Cand m. p. = 132-134 C, respectively

References: [1]Tetrahedron Letters,2002,vol. 43,p. 3551 - 3554.
[2]Organic Letters,2021,vol. 23,p. 3394 - 3398.
[3]Organic Letters,2020,vol. 22,p. 6557 - 6561.
[4]New Journal of Chemistry,2005,vol. 29,p. 769 - 772.
[5]Synlett,2009,p. 818 - 822.
[6]Patent: WO2012/52451,2012,A1 .Location in patent: Page/Page column 47.
[7]Archives of Pharmacal Research,2013,vol. 36,p. 436 - 447.
[8]Monatshefte fur Chemie,2016,vol. 147,p. 1819 - 1824.
[9]Synthetic Communications,2017,vol. 47,p. 1013 - 1019.
[10]Patent: WO2013/24149,2013,A1 .Location in patent: Page/Page column 44.
[11]Patent: US2013/210851,2013,A1 .Location in patent: Paragraph 0221-0226.
[12]Molecules,2017,vol. 22.
[13]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 689 - 695.
[14]European Journal of Organic Chemistry,2002,p. 2764 - 2769.
[15]Canadian Journal of Chemistry,1980,vol. 58,p. 2207 - 2211.
[16]Journal of the Chemical Society,1906,vol. 89,p. 200.
[17]Journal of Organic Chemistry,1970,vol. 35,p. 1632 - 1641.
[18]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2415 - 2425.
[19]Synthesis,2009,p. 985 - 999.
[20]Green Chemistry,2013,vol. 15,p. 1910 - 1924.
[21]Advanced Synthesis and Catalysis,2013,vol. 355,p. 2550 - 2557.
[22]Patent: WO2014/2058,2014,A2 .Location in patent: Page/Page column 75.
[23]Tetrahedron Letters,2014,vol. 55,p. 1686 - 1688.
[24]ACS Combinatorial Science,2015,vol. 17,p. 404 - 408.
[25]Research on Chemical Intermediates,2016,vol. 42,p. 3413 - 3423.
[26]Research on Chemical Intermediates,2016,vol. 42,p. 499 - 509.
[27]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[28]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[29]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[30]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[31]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[32]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[33]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[34]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[35]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[36]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[37]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[38]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[39]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[40]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[41]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[42]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[43]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[44]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[45]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[46]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[47]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[48]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[49]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[50]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[51]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[52]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[53]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[54]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[55]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[56]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[57]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[58]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[59]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[60]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[61]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[62]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[63]Tetrahedron Letters,2018,vol. 59,p. 3069 - 3076.
[64]International Journal of Environmental Research and Public Health,2018,vol. 15.
[65]Patent: WO2021/249449,2021,A1 .Location in patent: Page/Page column 110.
[66]Research on Chemical Intermediates,2022,vol. 48,p. 1515 - 1540.

2
[ 106-38-7 ]
[ 873-95-0 ]
[ 36646-78-3 ]

References: [1]Organic Letters,2000,vol. 2,p. 1109 - 1112.

3
[ 873-95-0 ]
[ 100-00-5 ]
[ 24706-49-8 ]

References: [1]Organic Letters,2000,vol. 2,p. 1109 - 1112.

4
[ 100-52-7 ]
[ 873-95-0 ]
[ 2769-21-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	In water; at 80℃; for 2h;	General procedure: A mixture of enaminone (2) (0.2 g, 1.4 mmol) and benzaldehyde (3a) (74 μL, 0.71 mmol)was heated in 10 mL of water at 80 C for 2 hours. The solid separated out was filtered offand dried in to provide light yellow solid (4a).

References: [1]Chemistry of Heterocyclic Compounds,2001,vol. 37,p. 1228 - 1233.
[2]Synthetic Communications,2017,vol. 47,p. 1013 - 1019.

5
[ 504-02-9 ]
[ 100-52-7 ]
[ 873-95-0 ]
3,3‑dimethyl‑9‑phenyl‑3,4,6,7,9,10‑hexahydroacridine‑1,8(2H,5H)‑dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		General procedure: An ethanolic solution of desired aldehyde (1 mmol) was added dropwise to thefreshly prepared linear β-enaminone (1 mmol) dissolved in 2 mL ethanol for20 min in a 25 mL round-bottom flask in an oil bath at 100 C. Then a solutionof cyclic 1,3-dicarbonyl (1 mmol) in 2 mL of ethanol was added dropwise to thismixture for 20 min. The obtained mixture was refluxed at 100 C until the maximumprogression of reaction, determined by TLC monitoring. Then, the reactionmixture was cooled to room temperature, solvent was removed under reducedpressure and the obtained solid stuff was purified by recrystallization from n-hexane/ethyl acetate

References: [1]Journal of Chemical Research,2006,p. 719 - 721.
[2]Research on Chemical Intermediates,2022,vol. 48,p. 1515 - 1540.

6
[ 504-02-9 ]
[ 123-11-5 ]
[ 873-95-0 ]
9‑(4‑nethoxyphenyl)‑3,3‑dimethyl‑3,4,6,7,9,10‑hexahydroacridine‑1,8(2H,5H)‑dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		General procedure: An ethanolic solution of desired aldehyde (1 mmol) was added dropwise to thefreshly prepared linear β-enaminone (1 mmol) dissolved in 2 mL ethanol for20 min in a 25 mL round-bottom flask in an oil bath at 100 C. Then a solutionof cyclic 1,3-dicarbonyl (1 mmol) in 2 mL of ethanol was added dropwise to thismixture for 20 min. The obtained mixture was refluxed at 100 C until the maximumprogression of reaction, determined by TLC monitoring. Then, the reactionmixture was cooled to room temperature, solvent was removed under reducedpressure and the obtained solid stuff was purified by recrystallization from n-hexane/ethyl acetate

References: [1]Journal of Chemical Research,2006,p. 719 - 721.
[2]Research on Chemical Intermediates,2022,vol. 48,p. 1515 - 1540.

7
[ 123-11-5 ]
[ 873-95-0 ]
[ 126-81-8 ]
[ 136203-55-9 ]

Yield	Reaction Conditions	Operation in experiment
70%		General procedure: An ethanolic solution of desired aldehyde (1 mmol) was added dropwise to thefreshly prepared linear β-enaminone (1 mmol) dissolved in 2 mL ethanol for20 min in a 25 mL round-bottom flask in an oil bath at 100 C. Then a solutionof cyclic 1,3-dicarbonyl (1 mmol) in 2 mL of ethanol was added dropwise to thismixture for 20 min. The obtained mixture was refluxed at 100 C until the maximumprogression of reaction, determined by TLC monitoring. Then, the reactionmixture was cooled to room temperature, solvent was removed under reducedpressure and the obtained solid stuff was purified by recrystallization from n-hexane/ethyl acetate

References: [1]Journal of Chemical Research,2006,p. 719 - 721.
[2]Research on Chemical Intermediates,2022,vol. 48,p. 1515 - 1540.

8
[ 873-95-0 ]
[ 126-81-8 ]
[ 100-10-7 ]
[ 3476-94-6 ]

Yield	Reaction Conditions	Operation in experiment
70%		General procedure: An ethanolic solution of desired aldehyde (1 mmol) was added dropwise to thefreshly prepared linear β-enaminone (1 mmol) dissolved in 2 mL ethanol for20 min in a 25 mL round-bottom flask in an oil bath at 100 C. Then a solutionof cyclic 1,3-dicarbonyl (1 mmol) in 2 mL of ethanol was added dropwise to thismixture for 20 min. The obtained mixture was refluxed at 100 C until the maximumprogression of reaction, determined by TLC monitoring. Then, the reactionmixture was cooled to room temperature, solvent was removed under reducedpressure and the obtained solid stuff was purified by recrystallization from n-hexane/ethyl acetate

References: [1]Journal of Chemical Research,2006,p. 719 - 721.
[2]Research on Chemical Intermediates,2022,vol. 48,p. 1515 - 1540.

9
[ 53931-59-2 ]
[ 873-95-0 ]
7,7-Dimethyl-2-phenethyl-7,8-dihydro-6H-quinolin-5-one hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		7,7-Dimethyl-2-phenethyl-7,8-dihydro-6H-quinolin-5-one hydrochloride A mixture of 4 A molecular sieves (140 mg), 5-phenylpent-1-en-3-one (Martin, R.; Romea, P.; Tey, C.; Urpi, F.; Vilarrasa, J.; SynLett. 1997, (12) 1414-1416.) (0.22 g, 1.4 mmol), <strong>[873-95-0]3-amino-5,5-dimethylcyclohex-2-en-1-one</strong>, and 10% Pd/C (14 mg) in toluene (4 ml) was heated at reflux for 4.5 h. It was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (chloroform-methanol, 30:1), then it was treated by a dry HCl solution in diethyl ether to give the title compound (0.2 g, 45%) as a colorless solid. Physical characteristics are as follows Mp 173-175 C.; 1H NMR (CDCl3, TMS) δ: 1.18, 2.63, 3.24, 3.62, 3.70, 7.15-7.30, 7.37, and 8.61; Anal. Found (C19H21NO*HCl) (%): C, 71.6; H, 7.0; N, 4.4.

References: [1]Patent: US2005/197361,2005,A1 .Location in patent: Page/Page column 23-24.

10
[ 873-95-0 ]
[ 6630-33-7 ]
9-(2-bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H, 5H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In water; at 80℃; for 2h;	General procedure: A mixture of enaminone (2) (0.2 g, 1.4 mmol) and benzaldehyde (3a) (74 μL, 0.71 mmol)was heated in 10 mL of water at 80 C for 2 hours. The solid separated out was filtered offand dried in to provide light yellow solid (4a).
		EXAMPLE 43 3-Amino-5,5-dimethyl-2-cyclohexen-1-one was reacted with 2-bromobenzaldehyde in an analogous manner to that described in Example 1 to give 9-(2-bromophenyl)-3,4,6,7,9,10-hexahydro-3,3,6,6-tetramethyl-1,8(2H,5H)-acridinedione. Crystallization from dimethylformamide/water gave a yellow powder of melting point >285 C. (decomposition).

References: [1]Synthetic Communications,2017,vol. 47,p. 1013 - 1019.
[2]Patent: US5969139,1999,A .

11
[ 98-03-3 ]
[ 873-95-0 ]
[ 343778-74-5 ]
[ 1315506-08-1 ]