5447-86-9

Usage

Chemical Properties

Light Yellow Solid

Uses

Derivative of Anthrone

InChI:InChI=1/C16H14O/c1-16(2)13-9-5-3-7-11(13)15(17)12-8-4-6-10-14(12)16/h3-10H,1-2H3

Synthetic route

9,9-Dimethyl-10-(trimethylsilyl)-9,10-dihydroanthracene (136590-96-0) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
With sodium dichromate; acetic acid for 12h; Ambient temperature;	90%
With sodium dichromate; acetic acid for 12h; Ambient temperature; other 9,9-dialkyl-10-(trimethylsilyl)- and 9,9-dialkyl-9,10-dihydroanthracenes;	90%

9-diazo-10,10-dimethyl-9,10-dihydroanthracene (85199-64-0) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 10-[10,10-dimethyl-9(10H)-anthracenyl]-9,10-dihydro-9,9-dimethylanthracene (85199-69-5)

Conditions	Yield
With (Z)-2-Butene Irradiation;	A 8% B 80%

9,10-Dihydro-10,10-dimethylanthracen (42332-94-5) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
With bromine In tetrachloromethane for 6h; Heating; Irradiation;	70%
With chromium(VI) oxide In acetic acid

(8aR,9R)-8a,9-Dimethyl-8a,9-dihydro-anthracen-9-ol (80716-32-1) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 9,10-Dihydro-10,10-dimethylanthracen (42332-94-5)

Conditions	Yield
With sulfuric acid; acetic anhydride In acetic acid	A 25% B 53%

9,9a-dihydro-9,9a-dimethyl-9-anthracenol (80716-32-1) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 9,10-Dihydro-10,10-dimethylanthracen (42332-94-5)

Conditions	Yield
With sulfuric acid; acetic anhydride In acetic acid at 23℃; for 2.25h;	A 25% B 53%

acetic anhydride (108-24-7) + 9,9a-dihydro-9,9a-dimethyl-9-anthracenol (80716-32-1) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 9,10-Dihydro-10,10-dimethylanthracen (42332-94-5) + 10,10-dimethyl-9,10-dihydroanthranylacetic acid (80716-37-6)

Conditions	Yield
With sulfuric acid for 2h; Yields of byproduct given;	A n/a B n/a C 45%

dimethylketene (598-26-5) + N-(10,10-dimethyl-9,10-dihydroanthracen-9-ylidene)phenylamine N-oxide (101023-20-5) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 4',4',10,10-tetramethyl-3'-phenyl-9,10-dihydroanthracene-9-spiro-2'-oxazolidin-5'-one (101023-21-6)

Conditions	Yield
In ethyl acetate Ambient temperature;	A 150 mg B 24%

2-(1-hydroxy-1-methyl-ethyl)-benzophenone cyclohemiacetal (1023-91-2) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
With sulfuric acid at 150℃; for 1.5h;	20%
With PPA
With sulfuric acid at 150 - 155℃; for 5h;	105 g

(8aR,9R)-8a,9-Dimethyl-8a,9-dihydro-anthracen-9-ol (80716-32-1) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 9,10-Dihydro-10,10-dimethylanthracen (42332-94-5) + 10,10-dimethyl-9,10-dihydroanthranylacetic acid (80716-37-6)

Conditions	Yield
	A 10% B 15% C 75 % Spectr.

anthracen-9(10H)-one (90-44-8) + methyl iodide (74-88-4) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
	12%
With potassium hydroxide
(i) Li, MeOH, toluene, (ii) /BRN= 969135/, tBuOH; Multistep reaction;
With lithium methanolate 1) toluene, 100-120 deg C; 140 deg C 2) tBuOH, 24 h, 140-150 deg C; Yield given. Multistep reaction;
With sodium hydroxide In dichloromethane at 20℃; for 15h;	100 % Spectr.

9-anthrol (529-86-2) + methyl iodide (74-88-4) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
Lithium-Verbindung;
With water; potassium carbonate

anthracen-9(10H)-one (90-44-8) + methyl iodide (74-88-4) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + methyl-9-methoxy-10-anthracene (21992-33-6)

Conditions	Yield
With potassium hydroxide

o-Isopropylbenzophenon-oxim (71104-02-4) + chloroacetic acid (79-11-8) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
(i) NaOH, aq. EtOH, (ii) K2S2O8, aq. NaOH; Multistep reaction;

9,10-dihydro-10,10-dimethyl-9-anthracenol (18792-73-9) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 9,10-Dihydro-10,10-dimethylanthracen (42332-94-5)

Conditions	Yield
With sulfuric acid In acetic acid for 3h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

methylene chloride (74-87-3) + 10-nitro-9-methylanthracene (84457-22-7) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
Yield given. Multistep reaction;

9,10-dihydro-10,10-dimethyl-9-anthracenol (18792-73-9) + acetic anhydride (108-24-7) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 9,10-Dihydro-10,10-dimethylanthracen (42332-94-5) + 10,10-dimethyl-9,10-dihydroanthranylacetic acid (80716-37-6)

Conditions	Yield
With sulfuric acid for 2h; Yields of byproduct given;

anthracen-9(10H)-one (90-44-8) + methyl iodide (74-88-4) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + methyl-9-methoxy-10-anthracene (21992-33-6) + 9-methoxyanthracene (2395-96-2) + 9,10-phenanthrenequinone (84-65-1)

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether 1.) toluene, 70 deg C, 2.) toluene, 70 deg C, 3.5 h; r.t. 12 h; Yield given. Multistep reaction. Yields of byproduct given;
With potassium hydroxide; 18-crown-6 ether 1.) toluene, 70 deg C, 2.) toluene, 70 deg C, 3.5 h; r.t. 12 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

anthracen-9(10H)-one (90-44-8) + methanol. lithium methylate → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
With toluene Erhitzen des Reaktionsprodukts mit CH3I und wenig tert-Butylalkohol;

anthracen-9(10H)-one (90-44-8) + methyl iodide (74-88-4) + KOH-solution → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

3,3-Dimethyl-3H-isobenzofuran-1-one (1689-09-4) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / diethyl ether / 0 °C 2: 20 percent / H2SO4 / 1.5 h / 150 °C View Scheme
Multi-step reaction with 2 steps 2: polyphosphoric acid View Scheme
Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 2 h / Reflux 1.2: 5 h / 20 °C 2.1: sulfuric acid / 5 h / 150 - 155 °C View Scheme

9a-hydro-9a-methyl-9-anthracenone (80716-28-5) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / diethyl ether / 1.) -70 deg C -> 0 deg C, 1 h, 2.) 23 deg C, 1 h 2: 25 percent / conc. sulfuric acid, acetic anhydride / acetic acid / 2.25 h / 23 °C View Scheme
Multi-step reaction with 2 steps 1: 71 percent 2: 25 percent / sulfuric acid, Ac2O / acetic acid View Scheme
Multi-step reaction with 2 steps 1: 71 percent 2: 10 percent View Scheme

C23H22N2O2S (85199-72-0) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / sodium methoxide / pyridine / 70 °C 2: 8 percent / cis-2-butene / Irradiation View Scheme

9-nitroanthracene (602-60-8) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

1,4,9a-trihydro-9a-methyl-9-anthracenone (80716-26-3) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.)Bromine 2.)DBU / 2.)benzene 2: 71 percent 3: 25 percent / sulfuric acid, Ac2O / acetic acid View Scheme
Multi-step reaction with 3 steps 1: 1.)Bromine 2.)DBU / 2.)benzene 2: 71 percent 3: 10 percent View Scheme
Multi-step reaction with 4 steps 1: 55 percent / methylenetriphenylphosphorane 2: 1.)Bromine 2.)DBU / 2.)benzene 3: 71 percent 4: 25 percent / sulfuric acid, Ac2O / acetic acid View Scheme
Multi-step reaction with 4 steps 1: 55 percent / methylenetriphenylphosphorane 2: 1.)Bromine 2.)DBU / 2.)benzene 3: 71 percent 4: 10 percent View Scheme

1,2,9a-trihydro-9a-methyl-9-anthracenone (80716-27-4) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.)Bromine 2.)DBU / 2.)benzene 2: 71 percent 3: 25 percent / sulfuric acid, Ac2O / acetic acid View Scheme
Multi-step reaction with 3 steps 1: 1.)Bromine 2.)DBU / 2.)benzene 2: 71 percent 3: 10 percent View Scheme

phthalic anhydride (85-44-9) → 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 2 h / Reflux 1.2: 2 h / 20 °C 2.1: magnesium; iodine / tetrahydrofuran / 2 h / Reflux 2.2: 5 h / 20 °C 3.1: sulfuric acid / 5 h / 150 - 155 °C View Scheme
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 2 h / Reflux 1.2: 2 h / 20 °C 2.1: magnesium; iodine / tetrahydrofuran / 2 h / Reflux 2.2: 5 h / 20 °C 3.1: sulfuric acid / 5 h / 150 - 155 °C View Scheme

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 3-(Dimethylamino)propyl chloride (109-54-6) → C20H25NO

Conditions	Yield
Stage #1: 3-(Dimethylamino)propyl chloride With iodine; magnesium In diethyl ether; ethylene dibromide at 30 - 35℃; for 9h; Reflux; Large scale; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In diethyl ether; ethylene dibromide at 10 - 35℃; for 1h; Reflux; Large scale;	97.2%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) → 10,10-dimethylanthrone hydrazone (90624-29-6)

Conditions	Yield
With hydrazine hydrochloride; hydrazine hydrate In various solvent(s) Heating;	95%
With hydrazinium sulfate; hydrazine Heating; Yield given;

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 9,10-Dibromoanthracene (523-27-3) → 10′-bromo-10,10-dimethyl-[9,9′-bianthracen]-9(10H)-ol

Conditions	Yield
Stage #1: 9,10-Dibromoanthracene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran; hexane at 20℃; for 16h; Inert atmosphere;	93%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + (4-bromophenyl)magnesium bromide (18620-02-5) → C22H19BrO

Conditions	Yield
In tetrahydrofuran at 60℃; for 24h; Grignard Reaction;	88%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 1.4-dibromobenzene (106-37-6) → C22H19BrO

Conditions	Yield
Stage #1: 1.4-dibromobenzene With magnesium In tetrahydrofuran for 4h; Inert atmosphere; Reflux; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 60℃; for 24h;	88%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) → 9,10-Dihydro-10,10-dimethylanthracen (42332-94-5)

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran for 2h; Reflux;	85%
With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether for 0.333333h; Heating;	27%
With potassium hydroxide; hydrazine hydrate In ethylene glycol
With hydrazine In diethylene glycol for 4h; Heating;

4-(4-bromophenyl)dibenzofuran (955959-84-9) + 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) → C34H26O2

Conditions	Yield
Stage #1: 4-(4-bromophenyl)dibenzofuran With magnesium In tetrahydrofuran for 4h; Inert atmosphere; Reflux; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;	85%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 4-(2-bromo-4-chlorophenyl)dibenzofuran → 9-(5-chloro-2-(dibenzofuran-4-yl)phenyl)-10,10-dimethyl-9,10-dihydroanthracen-9-ol

Conditions	Yield
Stage #1: 4-(2-bromo-4-chlorophenyl)dibenzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at -78 - 20℃; for 1h;	85%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + (4-(di([1,1’-biphenyl]-4-yl)amino)phenyl)boronic acid (943836-24-6) → C46H37N

Conditions	Yield
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: (4-(di([1,1’-biphenyl]-4-yl)amino)phenyl)boronic acid With potassium carbonate In toluene at 110℃; for 5h;	84%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + C44H39BN2O2 → C60H52N2

Conditions	Yield
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: C44H39BN2O2 With potassium carbonate In toluene at 110℃; for 5h;	84%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + C32H24BNO2 → C48H37N

Conditions	Yield
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: C32H24BNO2 With potassium carbonate In toluene at 110℃; for 5h;	83%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) → 2-bromo-10,10-dimethyl-10H-anthracen-9-one

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 18h; Darkness;	83%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 1-Bromo-5-chloronaphthalene (77332-65-1) → C26H21ClO

Conditions	Yield
Stage #1: 1-Bromo-5-chloronaphthalene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 0℃; for 10h; Inert atmosphere;	83%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 2-bromo-7-chloronaphthalene → C26H21ClO

Conditions	Yield
Stage #1: 2-bromo-7-chloronaphthalene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;	83%

2-(4-bromophenyl]pyridine (63996-36-1) + 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) → C27H23NO

Conditions	Yield
Stage #1: 2-(4-bromophenyl]pyridine With magnesium In tetrahydrofuran for 4h; Inert atmosphere; Reflux; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;	82%

bromobenzene (108-86-1) + 10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) → 10,10-dimethyl-9-phenyl-9,10-dihydroanthracen-9-ol (39615-41-3)

Conditions	Yield
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 3.5h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at -78 - 20℃; for 16h;	82%
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran at 40 - 80℃; for 4h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran for 15h; Inert atmosphere; Reflux;	76.8%
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran at 40 - 80℃; for 4h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran for 15h; Inert atmosphere; Reflux;	76.3%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 1-bromo-4-chloronaphthalene (53220-82-9) → C26H21ClO

Conditions	Yield
Stage #1: 1-bromo-4-chloronaphthalene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at 20℃; for 10h; Inert atmosphere;	82%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + C27H25BN2O3 → C43H38N2O

Conditions	Yield
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: C27H25BN2O3 With potassium carbonate In toluene at 110℃; for 5h;	81%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + C41H35BN2O2 → C57H48N2

Conditions	Yield
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: C41H35BN2O2 With potassium carbonate In toluene at 110℃; for 5h;	81%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) → C16H12N2O5

Conditions	Yield
With sulfuric acid; nitric acid at 5℃; for 0.5h;	80%
With sulfuric acid; nitric acid at 5 - 10℃; for 0.5h;	80%
With sulfuric acid; nitric acid at 5 - 10℃; for 0.5h;	80%
With nitric acid at 5 - 10℃; for 0.5h;	80%
With sulfuric acid; nitric acid at 5 - 10℃; for 0.5h;	80%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 4-(diphenylamino)phenyl boronic acid (201802-67-7) → C34H29N

Conditions	Yield
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: 4-(diphenylamino)phenyl boronic acid With potassium carbonate In toluene at 110℃; for 5h;	80%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 4-(di-naphthalene-2-yl-amino)-phenylboronic acid (1232102-18-9) → C42H33N

Conditions	Yield
Stage #1: 10,10-dimethyl-9,10-dihydroanthracen-9-one With toluene-4-sulfonic acid hydrazide In toluene at 80℃; for 2h; Stage #2: 4-(di-naphthalene-2-yl-amino)-phenylboronic acid With potassium carbonate In toluene at 110℃; for 5h;	80%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + (2,6-dimethylphenyl)magnesium bromide (21450-64-6) → 9-(2,6-xylyl)-10,10-dimethyl-9,10-dihydroanthracen-9-ol

Conditions	Yield
In tetrahydrofuran 1.) RT, 3 h, 2.) 80 deg C, 1 h;	78%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + C12H8BrClO → C28H21ClO

Conditions	Yield
Stage #1: C12H8BrClO With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran at -78 - 20℃; for 1h;	75.8%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + 2-bromo-4-chloro-1-phenoxybenzene → C28H21ClO

Conditions	Yield
Stage #1: 2-bromo-4-chloro-1-phenoxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: 10,10-dimethyl-9,10-dihydroanthracen-9-one In tetrahydrofuran Stage #3: With sulfuric acid; acetic acid Reflux;	75.58%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) + N,N-dimethylethylenediamine (108-00-9) → N'-(10,10-Dimethyl-10H-anthracen-9-ylidene)-N,N-dimethyl-ethane-1,2-diamine (76596-08-2)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; titanium tetrachloride In benzene for 144h; Ambient temperature;	69%

10,10-dimethyl-9,10-dihydroanthracen-9-one (5447-86-9) → C16H15(2)HO

Conditions	Yield
With water-d2; magnesium; ethylene dibromide In tetrahydrofuran at 70℃; for 2h; Inert atmosphere; Schlenk technique;	69%
With water-d2; magnesium; ethylene dibromide In tetrahydrofuran	69%

Upstream product

• 529-86-2 9-anthrol 
• 74-88-4 methyl iodide 
• 90-44-8 anthracen-9(10H)-one 
• 42332-94-5 9,10-Dihydro-10,10-dimethylanthracen 
• 71104-02-4 o-Isopropylbenzophenon-oxim 
• 79-11-8 chloroacetic acid 
• 598-26-5 dimethylketene 
• 101023-20-5 N-(10,10-dimethyl-9,10-dihydroanthracen-9-ylidene)phenylamine N-oxide 
• 18792-73-9 9,10-dihydro-10,10-dimethyl-9-anthracenol 
• 74-87-3 methylene chloride 
• 84457-22-7 10-nitro-9-methylanthracene 
• 108-24-7 acetic anhydride 
• 80716-32-1 (8aR,9R)-8a,9-Dimethyl-8a,9-dihydro-anthracen-9-ol 
• 80716-32-1 9,9a-dihydro-9,9a-dimethyl-9-anthracenol 

Downstream Products

• 18259-47-7 9,10,10-Trimethyl-9,10-dihydroanthranol 
• 39615-41-3 10,10-dimethyl-9-phenyl-9,10-dihydroanthracen-9-ol 
• 5118-29-6 melitracen 
• 62291-50-3 9-<2,6-Bis(1-methylethenyl)phenyl>-9,10-dihydro-10,10-dimethyl-9-anthracenol 
• 42332-98-9 10-p-Biphenyl-9,9-dimethyl-9,10-dihydroanthracen 
• 13577-30-5 9-Aethoxy-10,10-dimethyl-9-phenyl-9,10-dihydro-anthracen 
• 85118-29-2 C₂₁H₂₇NO 

Relevant academic research and scientific papers

Preparation method of 10,10-dimethylanthrone

The invention belongs to the field of drug synthesis and provides a novel method of synthesizing melitracen hydrochloride intermediate 10,10-dimethylanthrone. The 10,10-dimethylanthrone is prepared from phthalic anhydride as a start material through two-step Grignard reaction and three-step closed-ring reaction. The total yield is up to 30%, and the purity of the finished intermediate is higher than 98.0%. Compared with traditional synthetic processes, the novel process herein has simple steps and greatly reduced production cost, causes little environmental pollution and helps greatly solve the environmental issue caused by the production of 10,10-dimethylanthrone.

The effect of pressure on hydrogen transfer reactions with quinones

The effect of pressure on the oxidation of hydroarenes 3-9 with 2,3-dichloro-5,6-dicyano-1,4-quinone (DDQ; 1a) or o-chloranil (10), leading to the corresponding arenes, has been investigated. The activation volumes were determined from the pressure dependence of the rate constants of these reactions monitored by on-line UV/Vis spectroscopic measurements in an optical high-pressure cell (up to 3500 bar). The finding that they are highly negative and only moderately dependent on the solvent polarity (ΔV ?=-13 to -25 in MTBE and -15 to -29 cm3mol -1 in MeCN/AcOEt, 1:1) rules out the formation of ionic species in the rate-determining step and is good evidence for a hydrogen atom transfer mechanism leading to a pair of radicals in the rate-determining step, as was also suggested by kinetic measurements, studies of kinetic isotope effects, and spin-trapping experiments. The strong pressure dependence of the kinetic deuterium isotope effect for the reaction of 9,10-dihydroanthracene 5/5-9,9,10,10-D4 with DDQ (1a) can be attributed to a tunneling component in the hydrogen transfer. In the case of formal 1,3-dienes and enes possessing two vicinal C-H bonds, which have to be cleaved during the dehydrogenation, a pericyclic hydrogen transfer has to considered as one mechanistic alternative. The comparison of the kinetic deuterium isotope effects determined for the oxidation of tetralin 9/9-1,1,4,4-D4/9-2,2,3,3-D4/9-D 12 either with DDQ (1a) or with thymoquinone 1c indicates that the reaction with DDQ (1a) proceeds in a stepwise manner through hydrogen atom transfer, analogously to the oxidations of 1,4-dihydroarenes, whereas the reaction with thymoquinone 1c is concerted, following the course of a pericyclic hydrogen transfer. The difference in the mechanistic courses of these two reactions may be explained by the effect of the CN and Cl substituents in 1a, which stabilize a radical intermediate better than the alkyl groups in 1c. The mechanistic conclusions are substantiated by DFT calculations.

Regioselective alkylation of anthrone, 5,5-dimethyl-3-isoxazolidinone and 4-methylquinolone by phase transfer catalysis

Anthrone (1) can be alkylated selectively to give O-, C,O- or C,C-substituted compounds 2, 4, or 5, respectively. Similarly, 5,5-dimethyl-3-isoxazolidinone (6) and 4-methylquinolone (9) yield N- or O-derivatives 7 and 8 or 10 and 11, respectively. The product ratios can be influenced strongly sometimes by use of different phase transfer catalysts, but the sensitivity of each reaction towards the catalysts is unique.

Thermolabile Hydrocarbons, 34. - Thermal Stability of 9,9'-Bixanthene and 9,9',10,10'-Tetrahydro-10,10,10',10'-tetramethyl-9,9'-bianthracene. - Stabilisation Energies of Planar Benzhydryl Radicals

The thermal cleavage of the central CC bonds in the title compounds was investigated.The activation parameters were obtained from kinetics and the equilibrium enthalpies and entropies from the temperature dependence of the equilibrium radical concentrations, determined by quantitative ESR. ΔH(excit.) and ΔHDiss are nearly identical but not ΔS(excit.) and ΔSDiss, as expected.The radical stabilisation enthalpies RSE obtained from these data (RSE: 7a = 17.9+/-1.3; 7b = 15.6+/-1.4 kcal/mol) correspond closely to twice the RSE of α-phenylethyl radicals (8.0+/-1.5 kcal/mol) determined previously.The smaller RSE of the benzhydryl radical (12.9+/-0.9 kcal/mol), therefore, must be due to its nonplanarity. - Key Words: C-C Bond cleavage, energetics and kinetics of / Radicals, stability of / ESR

Free energy and entropy changes in vertical and nonvertical triplet energy transfer processes between rigid and nonrigid molecules. A laser photolysis study

The free energy and entropy changes associated with intermolecular triplet energy transfer (TT) processes were determined by direct measurement of the equilibrium constant using a laser flash photolysis technique. 10,10-Dimethylanthrone and 9,9-dimethylfluorene were synthesized and used as a "rigid" donor and acceptor, respectively, in comparison with 4-methylbenzophenone, a "nonrigid" donor, and 4-methylbiphenyl, a "nonrigid" acceptor, in the TT reactions. Both the nonrigid donor and the nonrigid acceptor lose entropy while going from the twisted ground state to the planar triplet state. The ΔS values for 4-methylbenzophenone and 4-methylbiphenyl are 0.5-1.0 and 2.5-3.0 gibbs/mol, respectively.

A Convenient Synthesis of 9,9-Dialkyl-9,10-dihydroanthracenes and 10,10-Dialkylanthrones: Silicon-Mediated Regioselective Dialkylation of 9,10-Dihydroanthracene

Described is a short and convenient approach to the synthesis of 9,9-dialkyl-9,10-dihydroanthracenes, 9,9,10-trialkyl-9,10-dihydroanthracenes, and 10,10-dialkylanthrones, some of which are otherwise unknown or inaccessible by conventional methods.Deprotonation of 9-(trimethylsilyl)-9,10-dihydroanthracene (2; 9-(trimethylsilyl)-9,10-DHA) followed by reaction with alkyl halides (RX) produces 9-alkyl-9-(trimethylsilyl)-9,10-DHAs 3-7 in 80-90percent yields.Treatment of 3-7 with n-BuLi produces the 10-lithio derivatives that rearrange to 9-alkyl-9-lithio-10-(trimethylsilyl) intermediates; subsequent alkylation with RX generates 9,9-dialkyl-10-(trimethylsilyl)-9,10-DHAs 8-19.Formation of single stereoisomers 13-19 was suggested by NMR and confirmed in two cases, 15 and 16, by X-ray structure determination.The trimethylsilyl group is removed by tetrabutylammonium fluoride (TBAF) to provide 9,9-dialkyl-9,10-DHAs 20-29 with impressive yields.Oxidation of either the 9,9-dialkyl-9,10-DHAs or 9,9-dialkyl-10-(trimethylsilyl)-9,10-DHAs with Cr(VI) oxidant furnished 10,10-dialkylanthrones 36-41 in 80-90percent yields.

Ketene. Part 23. Conformational Control of the Addition Reactions of Ketenes with N-Phenylnitrones

X-Ray analysis shows that the nitrone group in (5a) is not distorted, disproving a previous explanation for the formation of oxazolidinones rather than indolones in the reactions with ketenes.Nitrone (5c) reacts with dimethylketene and diphenylketene to form oxazolidinones (6c,d) whereas nitrones (5d) and (5e) under similar conditions form indolone derivatives (9).Oxazolidinone formation by the reaction of ketenes with nitrones (5a-c) results from restricted rotation about the N-phenyl bond preventing the -migration (3) -> (4), which precedes indolone formation.

REARRANGEMENT AND FRAGMENTATION REACTIONS OF BLOCKED AROMATIC ALCOHOLS.

A report is presented on the products obtained from reaction of alcohol and its secondary analogue with acidic solutions. It is found that in solutions containing acetic anhydride both give solely products resulting from molecular rearrangements. Factors responsible for determining the reaction products and reactivities of the starting alcohols are discussed.

DIHYDROSILAANTHRACENYLIDENE AND DIHYDROANTHRACENYLIDENE

Carbenes generated from 10-diazo-9,9-dimethyl-9,10-dihydro-9-silaanthracene and 10-diazo-9,9-dimethyl-9,10-dihydroanthracene gave hydrogen abstraction products by the triplet nature of these carbenes.The triplet dihyrosilaanthracenylidene was shown by the electron spin resonance study.