1,4-Naphthalenedione,2-(3-methyl-2-buten-1-yl)- supplier

Name
deoxylapachol
EINECS
CAS No. 3568-90-9
Article Data18
CAS DataBase
Density 1.125 g/cm³
Solubility
Melting Point
Formula C₁₅H₁₄O₂
Boiling Point 359.2 °C at 760 mmHg
Molecular Weight 226.275
Flash Point 134.8 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,4-Naphthalenedione,2-(3-methyl-2-butenyl)- (9CI);1,4-Naphthoquinone, 2-(3-methyl-2-butenyl)-(7CI,8CI);2-(3-Methyl-2-butenyl)-1,4-naphthoquinone;Deoxylapachol;Desoxylapachol;NSC 123507;
PSA 34.14000
LogP 3.34830

Synthetic route

: (1R*,4S*,4aR*,9aS*)-1,4,4a,9-tetrahydro-4a-prenyl-1,4-methanoanthracene-9,10-dione

: (1R*,4S*,4aS*,9aR*)-1,4,4a,9-tetrahydro-4a-prenyl-1,4-methanoanthracene-9,10-dione

: 3568-90-9
deoxylapachol

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene for 2h; Inert atmosphere; Reflux;	98%

: 114067-34-4
(3-methyl-2-butenyl)trifluorosilane

: 130-15-4
[1,4]naphthoquinone

: 3568-90-9
deoxylapachol

Conditions

Conditions	Yield
With iron(III) chloride In formamide for 24h; Ambient temperature;	96%
With iron(III) chloride In N,N-dimethyl-formamide; acetonitrile at 20℃;	96%

: 137414-53-0
1,4-dimethoxy-2-(3-methyl-2-butenyl)-naphthalene

: 3568-90-9
deoxylapachol

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile at 0℃; for 0.25h;	92%

: 1010-60-2
2-chloro-1,4-naphthoquinone

prenylindium sesquibromide: prenylindium sesquibromide

A: 3568-90-9
deoxylapachol

B: 82214-84-4
2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at -23℃; for 3h;	A 53% B 37%

...Expand

: 141550-13-2
4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane

: 130-15-4
[1,4]naphthoquinone

: 3568-90-9
deoxylapachol

Conditions

Conditions	Yield
In chloroform-d1 at 20℃; for 24h; Inert atmosphere;	53%

: 870-63-3
prenyl bromide

: 130-15-4
[1,4]naphthoquinone

: 3568-90-9
deoxylapachol

Conditions

Conditions	Yield
With lead(II) bromide; aluminium In acetonitrile for 10h;	50%
With zinc In tetrahydrofuran at 55 - 60℃; for 1.5h; Further byproducts given;	500 mg

: 114067-34-4
(3-methyl-2-butenyl)trifluorosilane

: 130-15-4
[1,4]naphthoquinone

A: 571-60-8
1,4-Dihydroxynaphthalene

B: 3568-90-9
deoxylapachol

C: 82214-84-4
2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at -20℃; for 1h;	A 38% B 28% C 32%

...Expand

: 130-15-4
[1,4]naphthoquinone

A: 571-60-8
1,4-Dihydroxynaphthalene

B: 3568-90-9
deoxylapachol

C: 82214-84-4
2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone

Conditions

Conditions	Yield
With (3-methyl-2-butenyl)trifluorosilane; tetrabutyl ammonium fluoride In tetrahydrofuran at -20℃; for 1h;	A 38% B 28% C 32%

...Expand

tricarbonyl<4-methoxy-2(3)-(3-methyl-2-butenyl)-1-naphthol>chromium(0): tricarbonyl<4-methoxy-2(3)-(3-methyl-2-butenyl)-1-naphthol>chromium(0)

: 3568-90-9
deoxylapachol

Conditions

Conditions	Yield
With silver(l) oxide	38%

: 504-85-8
4-methyl-pent-3-enoic acid

: 130-15-4
[1,4]naphthoquinone

A: 3568-90-9
deoxylapachol

B: 58880-17-4
2,3-di-(3-methyl-but-2-enyl)-1,4-naphthoquinone

Conditions

Conditions	Yield
With ammonium persulfate; silver nitrate In water; acetonitrile at 65 - 70℃; for 6h;	A 35% B 8%

...Expand

: 1010-60-2
2-chloro-1,4-naphthoquinone

: 870-63-3
prenyl bromide

A: 3568-90-9
deoxylapachol

B: 82214-84-4
2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone

Conditions

Conditions	Yield
With indium(III) chloride; water; zinc In tetrahydrofuran for 4h; Ambient temperature;	A 32% B 14%

...Expand

: 571-60-8
1,4-Dihydroxynaphthalene

: 115-18-4
2-methyl-3-buten-2-ol

: 3568-90-9
deoxylapachol

Conditions

Conditions	Yield
(i) BF3*Et2O, dioxane, (ii) Ag2O, Et2O; Multistep reaction;

: 504-85-8
4-methyl-pent-3-enoic acid

: 130-15-4
[1,4]naphthoquinone

: 3568-90-9
deoxylapachol

Conditions

Conditions	Yield
With ammonium peroxydisulfate; silver nitrate

: 1010-60-2
2-chloro-1,4-naphthoquinone

: 870-63-3
prenyl bromide

A: 3568-90-9
deoxylapachol

B: 82214-83-3
2-chloro-3-(3-methylbut-2-enyl)naphthalene-1,4-dione

C: 82214-85-5
2-chloro-2,3-dihydro-3,3-di-(3-methyl-but-2-enyl)-1,4-naphthoquinone

Conditions

Conditions	Yield
With zinc In tetrahydrofuran for 4h; Further byproducts given;	A 20 mg B 300 mg C 0.3 (unit not given)
With zinc In tetrahydrofuran for 4h; Further byproducts given;	A 20 mg B 300 mg C 0.3

...Expand

: 870-63-3
prenyl bromide

: 130-15-4
[1,4]naphthoquinone

A: 3568-90-9
deoxylapachol

B: 58880-17-4
2,3-di-(3-methyl-but-2-enyl)-1,4-naphthoquinone

C: 82214-84-4
2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone

Conditions

Conditions	Yield
With zinc In tetrahydrofuran at 55 - 60℃; for 4h;	A 20 mg B 400 mg C 1.2 (unit not given)
With zinc In tetrahydrofuran at 55 - 60℃; for 4h;	A 20 mg B 400 mg C 1.2

...Expand

: 571-60-8
1,4-Dihydroxynaphthalene

: 556-82-1
3-methyl-2-buten-1-ol

: 3568-90-9
deoxylapachol

Conditions

Conditions	Yield
(i) BF3-Et2O, dioxane, (ii) Ag2O, MgSO4, Et2O; Multistep reaction;

: 34168-56-4, 57231-36-4, 70368-23-9
catalponol

: 3568-90-9
deoxylapachol

Conditions

Conditions	Yield
With manganese(IV) oxide In benzene

: 130-15-4
[1,4]naphthoquinone

1.) prenylindium sequibromide: 1.) prenylindium sequibromide

A: 3568-90-9
deoxylapachol

B: 82214-84-4
2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone

Conditions

Conditions	Yield
With sodium sulfate; silver(l) oxide 1.) DMF, -23 deg C, 3 h, 2.) Et2O, reflux, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 3568-90-9
deoxylapachol

prenylindium sesquiiodide: prenylindium sesquiiodide

A: 137554-07-5
(Z)-2,3-benzo-5-methyl-5-(3,7-dimethylocta-2,6-dienyl)cyclohexane-1,4-dione

B: 82214-84-4
2,2-di-(3-methyl-but-2-enyl)-2,3-dihydro-1,4-naphthoquinone

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at -23℃; for 3h; Yields of byproduct given. Title compound not separated from byproducts;	A n/a B 100%

...Expand

: 3568-90-9
deoxylapachol

: 137492-06-9
2-(3-methyl-but-2-enyl)-2,3-epoxy-1,4-naphthoquinone

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium carbonate In water; acetone at 0℃;	82%

: 3568-90-9
deoxylapachol

: 4707-32-8
2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

Conditions

Conditions	Yield
With iron(III) chloride; toluene-4-sulfonic acid In water; toluene at 90℃; for 0.5h; Reagent/catalyst; Solvent;	76%

: 3568-90-9
deoxylapachol

: 1187181-61-8
hemitectol

Conditions

Conditions	Yield
With pyridine for 24h; Reflux; Inert atmosphere;	75%

: 3568-90-9
deoxylapachol

: 73377-79-4
(+)-2-(3-Methyl-2-butenyl)-1,4-naphthoquinone 2,3-epoxide

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide; N-benzylcinchonidinum chloride In water; toluene at 35 - 40℃;	53%

: 3568-90-9
deoxylapachol

: 90685-35-1
1.4-Dihydroxy-2-(3-methyl-buten-(2)-yl)-naphthalin

Conditions

Conditions	Yield
(i) SnCl2, aq. HCl, dioxane, (ii) ZnCl2; Multistep reaction;

: 3568-90-9
deoxylapachol

: 108-24-7
acetic anhydride

: 17532-55-7
2-(γ,γ-Dimethylallyl)-naphthohydrochinon-1,4-diacetat

Conditions

Conditions	Yield
With sodium acetate; zinc Heating;

: 3568-90-9
deoxylapachol

: 909576-31-4
2-(2,3-epoxy-3-methylbutyl)-1,4-naphthoquinone

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 16h;

: 3568-90-9
deoxylapachol

: 645413-83-8
6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: m-chloroperbenzoic acid / CH2Cl2 / 16 h / 20 °C 2.1: sodium dithionite / diethyl ether; H2O / 0.5 h / 20 °C 2.2: 1.26 g / acetic acid; sulfuric acid / H2O / 6 h / 20 °C 3.1: 90 percent / K2CO3 / acetone / 3 h / Heating View Scheme

: 3568-90-9
deoxylapachol

: 909576-35-8
5-bromo-6-methoxy-2,2-dimethyl-2H-naphtho[1,2-b]pyran

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: m-chloroperbenzoic acid / CH2Cl2 / 16 h / 20 °C 2.1: sodium dithionite / diethyl ether; H2O / 0.5 h / 20 °C 2.2: 1.26 g / acetic acid; sulfuric acid / H2O / 6 h / 20 °C 3.1: 90 percent / K2CO3 / acetone / 3 h / Heating 4.1: 95 percent / N-bromosuccinimide / CH2Cl2 / 0.17 h / 20 °C 5.1: pyridine / 16 h / 20 °C 6.1: 73 percent / KOtBu / tetrahydrofuran / 6 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: m-chloroperbenzoic acid / CH2Cl2 / 16 h / 20 °C
2.1: sodium dithionite / diethyl ether; H2O / 0.5 h / 20 °C
2.2: 1.26 g / acetic acid; sulfuric acid / H2O / 6 h / 20 °C
3.1: 90 percent / K2CO3 / acetone / 3 h / Heating
4.1: 95 percent / N-bromosuccinimide / CH2Cl2 / 0.17 h / 20 °C
5.1: pyridine / 16 h / 20 °C
6.1: 73 percent / KOtBu / tetrahydrofuran / 6 h / 20 °C
View Scheme

1,4-Naphthalenedione,2-(3-methyl-2-buten-1-yl)- Specification

The 1,4-Naphthalenedione,2-(3-methyl-2-buten-1-yl)-, with the CAS registry number 3568-90-9, is also known as Deoxylapachol. This chemical's molecular formula is C₁₅H₁₄O₂ and molecular weight is 226.27. What's more, its systematic name is 2-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione. It's a major sensitizer of teak wood.

Physical properties of 1,4-Naphthalenedione,2-(3-methyl-2-buten-1-yl)- are: (1)ACD/LogP: 4.25; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.25; (4)ACD/LogD (pH 7.4): 4.25; (5)ACD/BCF (pH 5.5): 991.99; (6)ACD/BCF (pH 7.4): 991.99; (7)ACD/KOC (pH 5.5): 4858.46; (8)ACD/KOC (pH 7.4): 4858.46; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 34.14 Å²; (13)Index of Refraction: 1.57; (14)Molar Refractivity: 66.02 cm³; (15)Molar Volume: 201 cm³; (16)Polarizability: 26.17×10^-24cm³; (17)Surface Tension: 41.7 dyne/cm; (18)Density: 1.125 g/cm³; (19)Flash Point: 134.8 °C; (20)Enthalpy of Vaporization: 60.47 kJ/mol; (21)Boiling Point: 359.2 °C at 760 mmHg; (22)Vapour Pressure: 2.42E-05 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(=CCC1=CC(=O)C2=CC=CC=C2C1=O)C
(2)InChI: InChI=1S/C15H14O2/c1-10(2)7-8-11-9-14(16)12-5-3-4-6-13(12)15(11)17/h3-7,9H,8H2,1-2H3
(3)InChIKey: OSDFYZPKJKRCRR-UHFFFAOYSA-N

Product Name

deoxylapachol

Synthetic route

1,4-Naphthalenedione,2-(3-methyl-2-buten-1-yl)- Specification

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