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33878-99-8

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Basic Information
CAS No.: 33878-99-8
Name: (S)-(+)-3,4,8,8A-TETRAHYDRO-8A-METHYL-1,6(2H,7H)-NAPHTHALENEDIONE
Article Data: 103
Molecular Structure:
Molecular Structure of 33878-99-8 ((S)-(+)-3,4,8,8A-TETRAHYDRO-8A-METHYL-1,6(2H,7H)-NAPHTHALENEDIONE)
Formula: C11H14O2
Molecular Weight: 178.231
Synonyms: 1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (S)-;1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (S)-(+)- (8CI);(+)-Wieland-Miescher ketone;(S)-1,2,3,4,6,7,8,8a-Octahydro-8a-methyl-1,6-naphthalenedione;(S)-Wieland-Miescher ketone;
Density: 1.1 g/cm3
Melting Point: 50-52 °C(lit.)
Boiling Point: 325.5 °C at 760 mmHg
Flash Point: 122 °C
Safety: 22-24/25
PSA: 34.14000
LogP: 2.03500
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Synthetic route
878-47-7, 4242-00-6, 34996-06-0, 50302-16-4, 70191-02-5, 34996-05-9

(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one

33878-99-8

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 17h; enantioselective reaction;97.9%
With jones reagent Oxidation;
5073-65-4

2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

33878-99-8

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions
ConditionsYield
With N-tosyl-(Sa)-1,1'-binaphthyl-2,2'-diamine-L-prolinamide; benzoic acid at 25℃; for 27h; Neat (no solvent); optical yield given as %ee; enantioselective reaction;95%
With N-tosyl-(Sa)-1,1'-binaphthyl-2,2'-diamine-L-prolinamide; benzoic acid for 168h; optical yield given as %ee; enantioselective reaction;94%
With L-proline at 20℃; for 2h; Catalytic behavior; Aldol Condensation; Ionic liquid; enantioselective reaction;88%
174851-52-6

14-noreudesma-4,11-dien-3,9-dione

33878-99-8

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions
ConditionsYield
Stage #1: 14-noreudesma-4,11-dien-3,9-dione With methanol; ozone
Stage #2: With ferrous(II) sulfate heptahydrate; thiophenol at -78 - 20℃; for 0.5h;		91%
5073-65-4

2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

A

33878-99-8

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B

100348-93-4

(R)-Wieland-Miescher ketone

Conditions
ConditionsYield
With L-proline at 20℃; for 2h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst; Aldol Condensation; Ionic liquid; enantioselective reaction;A 78%
B n/a
With (S)-2-(1-pyrrolidinylmethyl)pyrrolidine In dimethyl sulfoxide at 20℃; for 10h; Hajos-Parrish-Eder-Sauer-Wiechert reaction; optical yield given as %ee; enantioselective reaction;A 55%
B n/a
With (S)-2-(1-pyrrolidinylmethyl)pyrrolidine; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 48h; Hajos-Parrish-Eder-Sauer-Wiechert reaction; optical yield given as %ee; enantioselective reaction;A n/a
B 52%
5073-65-4

2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

A

33878-99-8

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B

20007-99-2, 33878-99-8, 100348-93-4, 20007-72-1

Wieland-Miescher ketone

Conditions
ConditionsYield
L-proline In N,N-dimethyl-formamide for 168h; Ambient temperature;A 36%
B 42%
20007-99-2, 33878-99-8, 100348-93-4, 20007-72-1

Wieland-Miescher ketone

A

9a-methyl-4,5,9,9a-tetrahydro-3H,8H-benzo[b]oxepine-2,7-dione

B

33878-99-8

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

C

100348-93-4

(R)-Wieland-Miescher ketone

D

257941-62-1

(-)-(4aR,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Conditions
ConditionsYield
With α-D-glucose 6-phosphate; oxygen; NADP; glucose-6-phosphate dehydrogenase; recombinant c-hexanone monooxygenase (E. coli TOP10 pQR239) In phosphate buffer at 20℃; for 26h; pH=8.7; Baeyer-Villiger oxidation; Further byproducts given;A 35%
B n/a
C n/a
D n/a
...Expand
5073-65-4

2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

A

33878-99-8

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B

N-[4-((R)-6-Fluoro-3-hydroxy-5-oxo-hexyl)-phenyl]-acetamide

C

N-[4-((3R,4S)-4-Fluoro-3-hydroxy-5-oxo-hexyl)-phenyl]-acetamide

Conditions
ConditionsYield
With antibody 38C2; PBS buffer In 1,2-dimethoxyethane for 504h; Ambient temperature; Yields of byproduct given. Title compound not separated from byproducts;A n/a
B 7%
C n/a
...Expand
5073-65-4

2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione

A

33878-99-8

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B

5004-80-8

6-hydroxy-1,6-dimethylbicyclo<3.3.1>nonane-2,9-dione

C

100348-93-4

(R)-Wieland-Miescher ketone

Conditions
ConditionsYield
With L-proline In N,N-dimethyl-formamide for 24h; Ambient temperature; Yield given. Title compound not separated from byproducts;
...Expand
51547-30-9

5β-hydroxy-5α-ethynyl-10β-methyl-Δ1(9)-octalin-2-one

33878-99-8

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

Conditions
ConditionsYield
With silver carbonate In dimethyl sulfoxide
20007-99-2, 33878-99-8, 100348-93-4, 20007-72-1

Wieland-Miescher ketone

A

33878-99-8

(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

B

257941-62-1

(-)-(4aR,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

Conditions
ConditionsYield
With D-glucose; yeast cells of Candida melibiosica IAM4488 In phosphate buffer at 30℃; for 68h; pH=6.5; Reduction; Enzymatic reaction;
Raw Materials
5073-65-4
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Specification

The CAS register number of 1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (8aS)- is 33878-99-8. It also can be called as 1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (S)- and the systematic name about this chemical is (8aS)-8a-methyl-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione. The molecular formula about this chemical is C11H14O2 and the molecular weight is 178.23.

Physical properties about 1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-, (8aS)- are: (1)ACD/LogP: 0.85; (2)#H bond acceptors: 2; (3)Polar Surface Area: 34.14 Å2; (4)Index of Refraction: 1.519; (5)Molar Refractivity: 48.81 cm3; (6)Molar Volume: 160.7 cm3; (7)Polarizability: 19.35x10-24cm3; (8)Surface Tension: 39.1 dyne/cm; (9)Density: 1.1 g/cm3; (10)Flash Point: 122 °C; (11)Enthalpy of Vaporization: 56.77 kJ/mol; (12)Boiling Point: 325.5 °C at 760 mmHg; (13)Vapour Pressure: 0.000229 mmHg at 25 °C.

When you are using this chemical, please be cautious about it as the following:
When you are using this chemical, avoid contact with skin and eyes and do not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1CCC/C2=C/C(=O)CC[C@]12C
(2)InChI: InChI=1/C11H14O2/c1-11-6-5-9(12)7-8(11)3-2-4-10(11)13/h7H,2-6H2,1H3/t11-/m0/s1
(3)InChIKey: DNHDRUMZDHWHKG-NSHDSACABU
(4)Std. InChI: InChI=1S/C11H14O2/c1-11-6-5-9(12)7-8(11)3-2-4-10(11)13/h7H,2-6H2,1H3/t11-/m0/s1
(5)Std. InChIKey: DNHDRUMZDHWHKG-NSHDSACASA-N