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CAS No.: | 33878-99-8 |
---|---|
Name: | (S)-(+)-3,4,8,8A-TETRAHYDRO-8A-METHYL-1,6(2H,7H)-NAPHTHALENEDIONE |
Article Data: | 103 |
Molecular Structure: | |
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 |
(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
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; |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
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% |
14-noreudesma-4,11-dien-3,9-dione
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
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% |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
(R)-Wieland-Miescher ketone
Conditions | Yield |
---|---|
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% |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
Wieland-Miescher ketone
Conditions | Yield |
---|---|
L-proline In N,N-dimethyl-formamide for 168h; Ambient temperature; | A 36% B 42% |
Wieland-Miescher ketone
B
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
C
(R)-Wieland-Miescher ketone
D
(-)-(4aR,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
Conditions | Yield |
---|---|
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 |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
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 |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
6-hydroxy-1,6-dimethylbicyclo<3.3.1>nonane-2,9-dione
C
(R)-Wieland-Miescher ketone
Conditions | Yield |
---|---|
With L-proline In N,N-dimethyl-formamide for 24h; Ambient temperature; Yield given. Title compound not separated from byproducts; |
5β-hydroxy-5α-ethynyl-10β-methyl-Δ1(9)-octalin-2-one
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
With silver carbonate In dimethyl sulfoxide |
Wieland-Miescher ketone
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
(-)-(4aR,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
Conditions | Yield |
---|---|
With D-glucose; yeast cells of Candida melibiosica IAM4488 In phosphate buffer at 30℃; for 68h; pH=6.5; Reduction; Enzymatic reaction; |
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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