thiochroman-4-ol
2,3-dihydro-4H-[1]benzothiopyran-4-one
Conditions | Yield |
---|---|
With dimethyl sulfoxide; triethylamine In dichloromethane at -40 - 20℃; for 8h; | 93% |
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 24h; Ambient temperature; | 92% |
With ammonium nitrate; hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In water; acetonitrile at 60℃; for 18h; Green chemistry; | 85% |
thiochroman-4-one semicarbazone
2,3-dihydro-4H-[1]benzothiopyran-4-one
Conditions | Yield |
---|---|
With potassium permanganate; silica gel In water at 20℃; for 0.416667h; | 91% |
Conditions | Yield |
---|---|
With PPA for 0.0166667h; microwave irradiation; | 80% |
With sulfuric acid at 110℃; for 4h; | 80% |
With PPA at 60℃; for 96h; | 66% |
4-(trimethylsilyloxy)thiochrom-3-ene
cyclohexanone
A
2,3-dihydro-4H-[1]benzothiopyran-4-one
B
3-cyclohexylidene-4-thiochromanone
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane 1.) -78 deg C; 2.) 25 deg C, 18 h; | A 63% B 32% |
4-(trimethylsilyloxy)thiochrom-3-ene
cyclopentanone
A
2,3-dihydro-4H-[1]benzothiopyran-4-one
B
thiochromen-4-one
C
3-cyclopentylidene-4-thiochromanone
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane 1.) -78 deg C; 2.) 25 deg C, 18 h; | A 24% B 20% C 22% |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86 percent / 0.06 h / microwave irradiation 2: 80 percent / polyphosphoric acid / 0.02 h / microwave irradiation View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ethanol / Heating 2: various solvent(s) / 1 h / 100 °C / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOH-solution 2: concentrated sulfuric acid / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: NaOH-solution 2: concentrated sulfuric acid / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: ethanol; water / 2 h / Reflux 2: sulfuric acid / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide |
ethyl 3-(phenylthio)propionate
2,3-dihydro-4H-[1]benzothiopyran-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol; water / Reflux 2: polyphosphoric acid / 100 °C View Scheme |
2-(phenylthio)acetaldehyde
2,3-dihydro-4H-[1]benzothiopyran-4-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: zinc; iodine / diethyl ether; benzene / 20 °C / Inert atmosphere 1.2: 24 h / Inert atmosphere 2.1: sodium hydroxide / methanol; water / Reflux 3.1: polyphosphoric acid / 100 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: polyphosphoric acid / 100 °C 2.1: zinc; iodine / diethyl ether; benzene / 20 °C / Inert atmosphere 2.2: 24 h / Inert atmosphere 3.1: sodium hydroxide / methanol; water / Reflux 4.1: polyphosphoric acid / 100 °C View Scheme |
2,3-dihydro-4H-[1]benzothiopyran-4-one
4-methyl-benzaldehyde
(Z)-3-(4-methylbenzylidene)thiochroman-4-one
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 3h; | 100% |
With sulfuric acid In acetic acid at 20℃; for 0.333333h; | 89% |
With hydrogenchloride In ethanol for 0.0833333h; Ambient temperature; | 64.1% |
With piperidine In chloroform for 5h; Reflux; | |
With sodium hydroxide In ethanol; water at 0℃; for 0.5h; |
2,3-dihydro-4H-[1]benzothiopyran-4-one
benzaldehyde
Z-3-benzylidene-1-thiochromanone
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 3h; | 100% |
With hydrogenchloride In ethanol | 79.6% |
With piperidine In chloroform for 5h; Reflux; | |
With sodium hydroxide In ethanol; water at 0℃; for 0.5h; |
2,3-dihydro-4H-[1]benzothiopyran-4-one
oxalic acid diethyl ester
3-ethoxalyl-2,3-dihydro-1-benzothiopyran-4-one
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol at 40℃; for 2h; | 100% |
With sodium In ethanol Claisen Condensation; |
2,3-dihydro-4H-[1]benzothiopyran-4-one
1-thiochroman-4-one 1-oxide
Conditions | Yield |
---|---|
With water; silica gel; magnesium monoperoxyphthalate hexahydrate In dichloromethane at 40℃; for 1h; | 100% |
With phthaloyl peroxide In dichloromethane at 25℃; for 8h; Schlenk technique; chemoselective reaction; | 99% |
With sodium bromate; ammonium cerium(IV) nitrate; silica gel In dichloromethane at 20℃; for 0.566667h; | 96% |
Conditions | Yield |
---|---|
With methanol; lithium hydride In benzene Reflux; Inert atmosphere; | 100% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
(R)-3,4-dihydro-2H-thiochromen-4-ol
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C49H64FeNOP; hydrogen; sodium t-butanolate In isopropyl alcohol at 25 - 30℃; under 38002.6 Torr; for 12h; Autoclave; enantioselective reaction; | 99% |
With (S)-2-[(1,3,2-dioxaborolan-2-yloxy)diphenylmethyl]pyrrolidine; dimethylsulfide borane complex In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 92% |
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium formate In water at 30℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 79% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
1,1-dioxo-1-thiochroman-4-one
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 40℃; for 0.333333h; | 99% |
With 3,3-dimethyldioxirane In dichloromethane; acetone at 0 - 5℃; | 96% |
With silica gel; magnesium monoperoxyphthalate hexahydrate In dichloromethane for 1.41667h; Heating; | 84% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
(S)-3,4-dihydro-2H-thiochromen-4-ol
Conditions | Yield |
---|---|
With formic acid; [RuCl2(hexamethylbenzene)]2; (S)-2-piperidinemethanethiol hydrochloride; triethylamine at 30℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
With Cp*Ir(OTf)(Msdpen); hydrogen In methanol at 60℃; under 11400.8 Torr; for 24h; optical yield given as %ee; enantioselective reaction; | 99% |
With formic acid; [RuCl2(hexamethylbenzene)]2; (S)-2-piperidinemethanethiol hydrochloride; triethylamine at 30℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With hydrogenchloride; mercury dichloride; zinc In toluene for 72h; Heating; | 98% |
With hydrogenchloride; amalgamated zinc In toluene for 72h; Heating; | 98% |
With molybdenum trisulfide; hydrogen In octane at 240℃; under 75006 Torr; for 1.5h; | 95% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
thiochroman-4-ol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 20℃; Inert atmosphere; | 98% |
With methanol; sodium tetrahydroborate at 0 - 20℃; for 0.666667h; Inert atmosphere; | 84% |
With potassium hydroxide; Cr(L-Ala)2 In water; N,N-dimethyl-formamide for 18h; Ambient temperature; pH=9.9; | 74% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
potassium cyanide
ammonium carbonate
spiro(hydantoin-5,4'-thiochromane)
Conditions | Yield |
---|---|
In ethanol; water at 55 - 60℃; Bucherer-Bergs reaction; | 98% |
chloro-trimethyl-silane
2,3-dihydro-4H-[1]benzothiopyran-4-one
4-(trimethylsilyloxy)thiochrom-3-ene
Conditions | Yield |
---|---|
With triethylamine; potassium iodide In chloroform 1.) chloroform, 0 deg C; 2.) reflux, 16 h; | 97% |
With triethylamine; potassium iodide In chloroform for 16h; Heating; | 94% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
phenylhydrazine
6,11-Dihydro-5-thia-11-aza-benzo[a]fluorene
Conditions | Yield |
---|---|
With chloro-trimethyl-silane In ethanol for 4h; Reflux; | 96% |
With chloro-trimethyl-silane In ethanol for 4h; Reflux; | 72% |
(i) AcOH, (ii) HCl; Multistep reaction; | |
With hydrogenchloride In 1,4-dioxane; ethanol for 4h; Fischer indole reaction; Heating; |
Conditions | Yield |
---|---|
Stage #1: ethyl trifluoroacetate, With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2,3-dihydro-4H-[1]benzothiopyran-4-one In tetrahydrofuran for 2h; Reflux; | 96% |
With sodium methylate In methanol; diethyl ether for 16h; |
2,3-dihydro-4H-[1]benzothiopyran-4-one
manganese triacetate
4-oxo-3,4-dihydro-2H-thiochromen-3-yl acetate
Conditions | Yield |
---|---|
With acetic acid In benzene for 5h; Heating; | 96% |
In benzene Heating; | 89% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
thiochroman-4-one oxime
Conditions | Yield |
---|---|
With pyridine; hydroxylamine hydrochloride at 20℃; for 1.5h; | 96% |
With hydroxylamine hydrochloride; sodium acetate In methanol at 20℃; for 12h; | 90% |
With pyridine; hydroxylamine hydrochloride at 20℃; for 3h; | 87% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
benzaldehyde
toluene-4-sulfonamide
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethylguanidine In toluene at 20℃; for 5h; Mannich reaction; Molecular sieve; optical yield given as %de; diastereoselective reaction; | 96% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
formic acid ethyl ester
3-(hydroxymethylene)thiochroman-4-one
Conditions | Yield |
---|---|
With sodium hydride In toluene | 95% |
With sodium methylate In pyridine for 18h; Ambient temperature; |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 3h; Condensation; Heating; | 95% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
A
1-thiochroman-4-one 1-oxide
B
1,1-dioxo-1-thiochroman-4-one
Conditions | Yield |
---|---|
With 3,3-dimethyldioxirane In dichloromethane; acetone at 0 - 5℃; | A 93% B 4.8% |
With dihydrogen peroxide; titanium(IV) isopropylate; L-Tartaric acid; silica gel In methanol; water at 25℃; for 24h; Title compound not separated from byproducts; | A 92 % Spectr. B 3% |
With sodium periodate Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 3h; Condensation; Heating; | 93% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
benzaldehyde
thiourea
4-phenyl-(5H)-(1-benzthiopyrano)-(4,3-d)-1,2,3,4-tetrahydropyrimidine-2-thione
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium hydrogen sulfate at 70℃; for 1h; Reagent/catalyst; Temperature; Green chemistry; | 92% |
With hydrogenchloride In butan-1-ol Heating; | 53.23% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
ethylhydrazine carboxylate
thiochroman-4-one ethoxy carbonylhydrazone
Conditions | Yield |
---|---|
With acetic acid In ethanol for 3h; Heating; | 92% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
benzaldehyde
thiourea
4-chlorobenzoylmethyl bromide
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-4H-[1]benzothiopyran-4-one; benzaldehyde; thiourea at 80℃; for 0.333333h; Ionic liquid; Stage #2: 4-chlorobenzoylmethyl bromide at 80℃; for 1h; Ionic liquid; | 92% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
benzaldehyde
thiourea
4-(bromoacetyl)toluene
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-4H-[1]benzothiopyran-4-one; benzaldehyde; thiourea at 80℃; for 0.333333h; Ionic liquid; Stage #2: 4-(bromoacetyl)toluene at 80℃; for 1h; Ionic liquid; | 92% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
4-methyl-benzaldehyde
thiourea
para-bromophenacyl bromide
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-4H-[1]benzothiopyran-4-one; 4-methyl-benzaldehyde; thiourea at 80℃; for 0.333333h; Ionic liquid; Stage #2: para-bromophenacyl bromide at 80℃; for 1h; Ionic liquid; | 92% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
4-chlorobenzaldehyde
4-Nitrophenacyl bromide
thiourea
Conditions | Yield |
---|---|
Stage #1: 2,3-dihydro-4H-[1]benzothiopyran-4-one; 4-chlorobenzaldehyde; thiourea at 80℃; for 0.333333h; Ionic liquid; Stage #2: 4-Nitrophenacyl bromide at 80℃; for 1h; Ionic liquid; | 92% |
2,3-dihydro-4H-[1]benzothiopyran-4-one
4-methoxy-benzaldehyde
thiourea
4-(4-methoxyphenyl)-3,4-dihydro-1H-thiochromeno[4,3-d]pyrimidine-2(5H)-thione
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium hydrogen sulfate at 70℃; for 1h; Green chemistry; | 92% |
Molecular Structure of Thiochroman-4-one (CAS NO.3528-17-4):
IUPAC Name: 2,3-dihydrothiochromen-4-one
Empirical Formula: C9H8OS
Molecular Weight: 164.2242
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 42.37 Å2
Index of Refraction: 1.624
Molar Refractivity: 46.71 cm3
Molar Volume: 132.2 cm3
Surface Tension: 49.1 dyne/cm
Density: 1.241 g/cm3
Flash Point: 154.9 °C
Enthalpy of Vaporization: 53.33 kJ/mol
Boiling Point: 293.7 °C at 760 mmHg
Vapour Pressure: 0.0017 mmHg at 25°C
Melting point: 28-30 °C(lit.)
InChI
InChI=1/C9H8OS/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-4H,5-6H2
Smiles
c12c(C(CCS1)=O)cccc2
EINECS: 222-548-1
Product Categories: Heterocyclic Compounds; Heterocyclic Building Blocks; Others; S-Containing
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
Thiochroman-4-one , with CAS number of 3528-17-4, can be called 1-Thiochroman-4-one ; 2,3-Dihydro-4-benzothiopyranone ; 2,3-Dihydro-4H-1-benzothiopyran-4-one ; 2,3-Dihydro-4H-thiochromen-4-one . It is an orange low melting solid.
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View