86-44-2|3-Benzyl-7-hydroxy-4-methyl-2H-chromen-2-one| Ambeed

CAS No. :	86-44-2
Formula :	C₁₇H₁₄O₃
M.W :	266.29
SMILES Code :	O=C1C(CC2=CC=CC=C2)=C(C)C3=C(O1)C=C(O)C=C3
MDL No. :	MFCD00047643
InChI Key :	IDFOCEQDKOOOER-UHFFFAOYSA-N
Pubchem ID :	5338538

Safety of [ 86-44-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P264-P270-P301+P312-P330-P501

Application In Synthesis of [ 86-44-2 ]

* 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 [ 86-44-2 ]

[ 86-44-2 ] Synthesis Path-Downstream 1~54

1
[ 86-44-2 ]
3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl benzoate [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1929,vol. 6,p. 801.

2
3-benzyl-7-hydroxy-4-methyl-2-oxo-2H-chromene-6-carboxylic acid [ No CAS ]
[ 86-44-2 ]

References: [1]Journal of the Indian Chemical Society,1938,vol. 15,p. 383,387.

3
[ 620-79-1 ]
[ 108-46-3 ]
[ 86-44-2 ]

Yield	Reaction Conditions	Operation in experiment
	at 65℃; for 4h;	General procedure: To a stirred solution of the above mentioned products in PPA 3 g,resorcino (1 eq) was added. The reaction mixture was stirred at65 C for 4 h. The mixture solution had to rest overnight, thendiluted with 100 mL water. The precipitated solid was filtered off,washed with water to give the crude product. The crude productwas purified by silica gel chromatography using cyclohexane-ethylacetate as eluate to give 7-hydroxy-chromen-2-one derivatives(67%).

References: [1]Green Chemistry,2022,vol. 24,p. 2429 - 2437.
[2]Molecules,2013,vol. 18,p. 6057 - 6091.
[3]Journal of the Chemical Society,1915,vol. 107,p. 431.
[4]Journal of the Indian Chemical Society,1931,vol. 8,p. 129,132.
Journal of the Indian Chemical Society,1935,vol. 12,p. 536,539.
[5]Journal of the Indian Chemical Society,1953,vol. 30,p. 743,745.
[6]Journal of the Indian Chemical Society,1935,vol. 12,p. 536,539.
[7]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.
[8]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 272 - 275.
[9]European Journal of Medicinal Chemistry,2020,vol. 204.

4
[ 110-91-8 ]
[ 50-00-0 ]
[ 86-44-2 ]
3-benzyl-7-hydroxy-4-methyl-8-morpholin-4-ylmethyl-chromen-2-one [ No CAS ]

References: [1]Journal of the Indian Chemical Society,1964,vol. 41,p. 200 - 202.

5
[ 86-44-2 ]
KOH-solution [ No CAS ]
[ 2550-26-7 ]
[ 89-86-1 ]

References: [1]Journal of the Chemical Society,1915,vol. 107,p. 431.

Yield	Reaction Conditions	Operation in experiment
48%		General procedure: Substituted aniline IV (1 eq) was added portionwise to theketo ester III (3 eq.) preheated to 160 C. under nitrogen. Thereaction was allowed to stir until TLC showed complete disappearance of starting aniline. The reaction was cooled to anddiluted with a 1:1 mixture of heptanes and diethyl ether. Theresultant solid was filtered and dried to get the crude productwhich was used in the next step without further purification.This product was added to methanesulfonic acid (5 vol) preheated to 85 C. The reaction was allowed to stir at thattemperature (15-60 mins) until TLC showed complete disappearance of starting material. The reaction mixture wascooled to room temperature and ice water (15 vol) was addedto it. The resultant solid was filtered, washed with aq. Sodiumbicarbonate and water and dried to get the pure V. Details ofcompounds are given in Table 2.

7
[ 7446-70-0 ]
[ 98-95-3 ]
[ 620-79-1 ]
[ 108-46-3 ]
[ 86-44-2 ]

References: [1]Journal of the Indian Chemical Society,1953,vol. 30,p. 743,745.

8
[ 98-03-3 ]
[ 86-44-2 ]
3-benzyl-7-hydroxy-4-(2-hydroxy-2-thiophen-2-yl-ethyl)-chromen-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

9
[ 50-00-0 ]
[ 86-44-2 ]
3-benzyl-7-hydroxy-4-(2-hydroxy-ethyl)-chromen-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

10
[ 2100-17-6 ]
[ 86-44-2 ]
3-benzyl-7-hydroxy-4-(2-hydroxy-hex-5-enyl)-chromen-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

11
[ 86-44-2 ]
[ 105-07-7 ]
4-[2-(3-benzyl-7-hydroxy-2-oxo-2H-chromen-4-yl)-1-hydroxy-ethyl]-benzonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

12
[ 86-44-2 ]
[ 2043-61-0 ]
3-benzyl-4-(2-cyclohexyl-2-hydroxy-ethyl)-7-hydroxy-chromen-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

13
[ 86-44-2 ]
benzyl halide [ No CAS ]
3-benzyl-7-hydroxy-4-phenethyl-chromen-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

14
[ 86-44-2 ]
dimethyl-carbamic acid 3-benzyl-4-(2-hydroxy-ethyl)-2-oxo-2H-chromen-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

15
[ 86-44-2 ]
dimethyl-carbamic acid 3-benzyl-2-oxo-4-phenethyl-2H-chromen-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

16
[ 86-44-2 ]
dimethyl-carbamic acid 3-benzyl-4-(2-hydroxy-2-thiophen-2-yl-ethyl)-2-oxo-2H-chromen-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

17
[ 86-44-2 ]
dimethyl-carbamic acid 3-benzyl-4-(2-hydroxy-hex-5-enyl)-2-oxo-2H-chromen-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

18
[ 86-44-2 ]
dimethyl-carbamic acid 3-benzyl-4-(2-cyclohexyl-2-hydroxy-ethyl)-2-oxo-2H-chromen-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

19
[ 86-44-2 ]
dimethyl-carbamic acid 3-benzyl-4-[2-(4-cyano-phenyl)-2-hydroxy-ethyl]-2-oxo-2H-chromen-7-yl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 2411 - 2415.

20
[ 2150-47-2 ]
[ 86-44-2 ]

References: [1]Journal of the Indian Chemical Society,1938,vol. 15,p. 383,387.

21
3-benzyl-7-hydroxy-4-methyl-2-oxo-2H-chromene-6-carboxylic acid methyl ester [ No CAS ]
[ 86-44-2 ]

References: [1]Journal of the Indian Chemical Society,1938,vol. 15,p. 383,387.

22
[ 620-79-1 ]
[ 86-44-2 ]

References: [1]Journal of the Indian Chemical Society,1938,vol. 15,p. 383,387.

23
[ 86-44-2 ]
3-methyl-1-(morpholin-4-ylcarbonyl)-1H-imidazol-3-ium iodide [ No CAS ]
Morpholine-4-carbamic Acid 3-(benzyl)-4-methyl-2-oxo-2H-chromen-7-yl Ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Morpholine-4-carbamic Acid 3-(benzyl)-4-methyl-2-oxo-2H-chromen-7-yl Ester The title compound was prepared from 3-(benzyl)-7-hydroxy-4-methyl-2H-chromen-2-one and 1-methyl-3-(morpholine-4-carbonyl)-3H-imidazol-1-ium iodide. HPLC-MS m/z=380 (M+1), Rt: 4.05 min.

References: [1]Patent: US2003/166644,2003,A1 .

24
[ 86-44-2 ]
1-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)-3-methyl-1H-imidazol-3-ium iodide [ No CAS ]
[ 548764-73-4 ]

Yield	Reaction Conditions	Operation in experiment
		3,4-Dihydro-2H-quinoline-1-carboxylic Acid 3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl Ester The title compound was prepared from <strong>[86-44-2]3-benzyl-7-hydroxy-4-methyl-2H-chromen-2-one</strong> and 3-(3,4-dihydro-2H-quinoline-1-carbonyl)-1-methyl-3H-imidazol-1-ium iodide. HPLC-MS m/z=426 (M+1), Rt: 5.34 min.

References: [1]Patent: US2003/166644,2003,A1 .

25
[ 86-44-2 ]
3-methyl-1-[methyl(phenyl)amino]carbonyl}-1H-imidazol-3-ium iodide [ No CAS ]
[ 548764-31-4 ]

Yield	Reaction Conditions	Operation in experiment
		Methyl-phenyl-carbamic Acid 3-(benzyl)-4-methyl-2-oxo-2H-chromen-7-yl Ester The title compound was prepared from <strong>[86-44-2]3-benzyl-7-hydroxy-4-methyl-2H-chromen-2-one</strong> and 3-(methyl-phenyl-carbamoyl)-1-methyl-3H-imidazol-1-ium iodide. HPLC-MS m/z=400 (M+1), Rt: 4.90 min.

References: [1]Patent: US2003/166644,2003,A1 .

26
[ 108-46-3 ]
[ 433733-19-8 ]
[ 86-44-2 ]

References: [1]Journal of Organic Chemistry,2012,vol. 77,p. 6530 - 6537.

27
[ 100-39-0 ]
[ 86-44-2 ]

References: [1]Molecules,2013,vol. 18,p. 6057 - 6091.
[2]European Journal of Medicinal Chemistry,2020,vol. 204.

28
[ 86-44-2 ]
[ 79-44-7 ]
[ 393810-34-9 ]

References: [1]Molecules,2013,vol. 18,p. 6057 - 6091.

29
[ 86-44-2 ]
[ 88-10-8 ]
[ 1428239-08-0 ]

References: [1]Molecules,2013,vol. 18,p. 6057 - 6091.

30
[ 86-44-2 ]
[ 75-36-5 ]
3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl acetate [ No CAS ]

References: [1]Molecules,2013,vol. 18,p. 6057 - 6091.

31
[ 86-44-2 ]
[ 79-03-8 ]
[ 312941-17-6 ]

References: [1]Molecules,2013,vol. 18,p. 6057 - 6091.

32
[ 86-44-2 ]
[ 638-29-9 ]
[ 1428238-96-3 ]

References: [1]Molecules,2013,vol. 18,p. 6057 - 6091.

33
[ 86-44-2 ]
[ 3282-30-2 ]
[ 1428238-95-2 ]

References: [1]Molecules,2013,vol. 18,p. 6057 - 6091.

34
[ 86-44-2 ]
[ 98-88-4 ]
3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl benzoate [ No CAS ]

References: [1]Molecules,2013,vol. 18,p. 6057 - 6091.

35
[ 86-44-2 ]
[ 141-75-3 ]
[ 1428238-78-1 ]

References: [1]Molecules,2013,vol. 18,p. 6057 - 6091.

36
[ 86-44-2 ]
[ 98-09-9 ]
[ 780790-52-5 ]

References: [1]Molecules,2013,vol. 18,p. 6057 - 6091.

37
[ 86-44-2 ]
[ 98-59-9 ]
[ 1428238-97-4 ]

References: [1]Molecules,2013,vol. 18,p. 6057 - 6091.

38
[ 50-00-0 ]
[ 86-44-2 ]
aloperine [ No CAS ]
8-[(6aR,13aS)-3,4,6,7,8,9,10,12,13,13a-decahydro-2H-6,13-methanodipyrido[1,2-a:3',2'-e]azocin-1(6aH)-ylmethyl]-3-benzyl-7-hydroxy-4-methyl-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	In 1,4-dioxane;Reflux;	General procedure: A solution containing 1 (0.51 g, 2.2 mol) and formalinsolution (1 mL, 35%) in dioxane (5 mL) was stirred vigorously at room temperature for 30 min, treated with the appropriatehydroxycoumarin (2-16, 2 mmol), stirred vigorously with heating (90-100C) for 5-20 h (end of reaction determined byTLC), and evaporated in vacuo. The resulting solid or oily residue was crystallized from MeOH.

References: [1]Chemistry of Natural Compounds,2017,vol. 53,p. 444 - 447.
Khim. Prir. Soedin.,2017,p. 378 - 381,4.

39
[ 100-39-0 ]
[ 141-97-9 ]
[ 108-46-3 ]
[ 86-44-2 ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 502 - 506.

40
[ 86-44-2 ]
4-(2-((3-benzyl-4-methyl-2-oxo-2H-chromen-7-yl)oxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole 2-oxide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 502 - 506.

41
[ 86-44-2 ]
[ 107-07-3 ]
3-benzyl-7-(2-hydroxyethoxy)-4-methyl-2H-chromen-2-one [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 502 - 506.

42
[ 86-44-2 ]
C₆H₉BrN₂S [ No CAS ]
3-benzyl-4-methyl-7-(3-(thiazol-2-ylamino)propoxy)-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	With tetra-(n-butyl)ammonium iodide; caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 31h;	To a solution of <strong>[86-44-2]3-benzyl-7-hydroxy-4-methyl-2H-chromen-2-one</strong> (0.338 mmol) in DMF (2 mL) was added TBAI (2.2 eq) andCsCO3 (2 eq). To the resulting solution, the above-mentionedproducts (2 eq) was added dropwise. The mixture was stirred for31 h at 100 C, followed by addition of 2mL water. The mixture wasextracted with 2 10 mL ethyl acetate, and the organic phase wasdried over anhydrous Na2SO4 and concentrated. The residue waspurified by column chromatography on silica gel (hexane-EtOAc) togive compound NO.52. Yield: 21%.1H NMR (600 MHz, DMSO) d 7.73 (d, J 8.5 Hz, 1H), 7.61 (s, 1H),7.27 (d, J 7.5, Hz, 2H), 7.23 (d, J 7.4 Hz, 2H), 7.18 (t, J 7.2 Hz,1H),7.01 (d, J 3.6 Hz, 1H), 6.97 (d, J 2.4 Hz, 1H), 6.61 (d, J 3.6 Hz,1H), 4.16 (t, J 6.2 Hz, 2H), 3.99 (t, J 6.4 Hz, 1H), 3.95 (d,J 10.0 Hz, 2H), 3.93e3.85 (m, 2H), 3.45e3.38 (m, 2H), 2.72 (t,J 8.3 Hz, 2H), 2.70e2.62 (m, 2H), 2.57 (dd, J 12.7, 6.3 Hz, 1H),2.44 (s, 3H), 2.29 (s, 2H),1.63 (dd, J 12.0, 6.0 Hz, 1H),1.40e1.33 (m,1H), 1.30 (d, J 8.5 Hz, 3H), 0.93e0.82 (m, 3H). ESI-MS m/z: 407.00[MH] .13C NMR (151 MHz, DMSO) d 169.65 (s), 161.71 (s), 161.49 (s),153.84 (s), 148.84 (s), 139.79 (s), 139.23 (s), 128.89 (s), 128.49 (s),127.08 (s), 126.53 (s), 121.49 (s), 114.01 (s), 112.97 (s), 106.45 (s),101.43 (s), 66.42 (s), 41.69 (s), 32.60 (s), 28.67 (s), 15.66 (s).