Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; C52H46O2P2Pd2; triphenylphosphine In toluene at 60℃; under 760.051 Torr; for 2.16667h; Conversion of starting material; | 100% |
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 25℃; under 760 Torr; for 24h; | 71% |
Conditions | Yield |
---|---|
In tert-butyl alcohol | 95.1% |
Multi-step reaction with 3 steps 1: methanol 2: zinc chloride; tetrachloromethane / Erhitzen des Reaktionsprodukts mit Kaliumcyanid in wss. Aethanol 3: aqueous sulfuric acid View Scheme |
α-chloro-α'-cyano-o-xylene
A
isochroman-3-one
B
α-hydroxy-α'-cyano-o-xylene
Conditions | Yield |
---|---|
With hydrogenchloride In water at 150℃; under 3677.86 Torr; for 3h; | A 95% B n/a |
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 240h; | 90% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 24h; Ambient temperature; | 90% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane | 90% |
carbon monoxide
phthalyl alcohol
A
isochroman-3-one
B
o-xylene
C
o-methylphenylacetic acid
Conditions | Yield |
---|---|
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction; | A 88% B n/a C 9% |
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 120℃; under 68400 Torr; for 42h; Carbonylation; reduction; | A 13% B n/a C 52% |
Conditions | Yield |
---|---|
With water; N-ethyl-N,N-diisopropylamine In tert-Amyl alcohol at 40 - 70℃; under 3087.28 - 3475.15 Torr; Product distribution / selectivity; | 84.53% |
With water; N-ethyl-N,N-diisopropylamine In tert-Amyl alcohol at 70℃; under 1551.49 Torr; Product distribution / selectivity; | 80.95% |
With water; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium dichloride In tert-Amyl alcohol at 70 - 75℃; under 3863.02 Torr; for 4h; Product distribution / selectivity; | 75.4% |
With water; N-ethyl-N,N-diisopropylamine; hydrogen tetrachloropalladate; triphenylphosphine In tert-Amyl alcohol at 70℃; under 3102.97 - 3863.02 Torr; for 2 - 4h; Product distribution / selectivity; | 69.9% |
2-chloromethylphenylacetic acid
isochroman-3-one
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water at 50℃; for 0.5h; Temperature; | 84.1% |
With hydrogenchloride; potassium hydrogencarbonate In fluorobenzene; cyclohexane | |
With potassium hydrogencarbonate In water at 50℃; pH=7.2; pH-value; Temperature; Reagent/catalyst; | 39 g |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; dihydrotetrachloropalladium (H2PdCl4) In o-xylene; water | 83.9% |
Conditions | Yield |
---|---|
With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran 1.) 20 deg C, 0.5 h; 2.) -78 deg C, 1 h; | 82% |
With naphthalene; lithium 1.) THF, 0 deg C, 2 h, 2.) THF, -40 deg C, 5 min; Yield given. Multistep reaction; | |
With naphthalene; lithium 1) THF, 0 deg C, 1.5 h, 2) THF, -40 deg C, 5 min; Yield given. Multistep reaction; |
α-chloro-α'-cyano-o-xylene
A
isochroman-3-one
D
α-hydroxy-α'-cyano-o-xylene
Conditions | Yield |
---|---|
With hydrogenchloride In water at 100℃; for 6h; | A 76% B n/a C n/a D n/a |
In water at 150℃; under 3677.86 Torr; for 3h; | A 75% B n/a C n/a D n/a |
tert-Amyl alcohol
o-Xylylene dichloride
N-ethyl-N,N-diisopropylamine
isochroman-3-one
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; triphenylphosphine; dihydrotetrachloropalladium (H2PdCl4) In o-xylene; water | 75.8% |
tert-Amyl alcohol
o-Xylylene dichloride
triphenylphosphine
isochroman-3-one
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; carbon monoxide; N-ethyl-N,N-diisopropylamine; palladium(II) chloride In water | 75.4% |
2-(ethoxycarbonylmethyl)benzoic acid
isochroman-3-one
Conditions | Yield |
---|---|
With dimethylsulfide borane complex In tetrahydrofuran at 40℃; Inert atmosphere; | 75% |
Conditions | Yield |
---|---|
With hydrogenchloride; calcium hydroxide; carbon monoxide; triphenylphosphine In water; dichlorobis(triphenylphosphine)palladium[II]; tert-butyl alcohol | 72.9% |
palladium(II) chloride In 1-methyl-pyrrolidin-2-one; water; tert-butyl alcohol | 66.4% |
With hydrogenchloride; sodium hydroxide; carbon monoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium chloride (PdCl2) In o-xylene; water; tert-butyl alcohol |
isochroman-3-one
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In chloroform at 80℃; for 2h; | 70% |
N-phenyl-maleimide
1,2-dihydrocyclobutabenzene-1-carboxylic acid
A
isochroman-3-one
B
(3aR,4S,9aR)-1,3-Dioxo-2-phenyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindole-4-carboxylic acid
(3aS,4S,9aS)-1,3-Dioxo-2-phenyl-2,3,3a,4,9,9a-hexahydro-1H-benzo[f]isoindole-4-carboxylic acid
Conditions | Yield |
---|---|
In benzene-d6 at 140℃; for 3h; | A 19% B 13% C 68% |
Conditions | Yield |
---|---|
Stage #1: o-methylphenylacetic acid With sulfuryl dichloride; 2,2'-azobis(isobutyronitrile) In fluorobenzene at 75 - 80℃; for 4h; Stage #2: With potassium hydroxide; potassium hydrogencarbonate; potassium iodide In fluorobenzene; water at 60℃; pH=6.3; Conversion of starting material; | 68% |
With iodobenzene; 3-chloro-benzenecarboperoxoic acid; potassium bromide In 2,2,2-trifluoroethanol at 20℃; for 24h; | 67% |
Stage #1: o-methylphenylacetic acid With sulfuryl dichloride; 2,2'-azobis(isobutyronitrile) In chlorobenzene at 75 - 80℃; for 4h; Stage #2: With potassium hydroxide; potassium hydrogencarbonate; potassium iodide In water; chlorobenzene at 60℃; pH=6.5; Conversion of starting material; | 61.5% |
o-(methoxycarbonylmethyl)benzoic acid
isochroman-3-one
Conditions | Yield |
---|---|
Stage #1: o-(methoxycarbonylmethyl)benzoic acid With borane In tetrahydrofuran at -15 - 20℃; for 16h; Stage #2: With toluene-4-sulfonic acid In toluene at 80℃; for 3h; | 66% |
isochroman-3-one
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In chloroform | 65% |
2-(2-hydroxyethyl)benzyl alcohol
A
isochroman-3-one
B
isochroman-1-one
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 9-azabicyclo<3.3.1>nonane-N-oxyl In acetonitrile at 22℃; for 2h; regioselective reaction; | A 18% B 58% |
With iodosylbenzene; potassium bromide In water for 2h; sonication; | |
With [(η5-C5Me5)Ir(6,6'-dihydroxy-2,2'-bipyridine)(H2O)]OTf2 In water for 20h; Inert atmosphere; Reflux; Green chemistry; Overall yield = 88 %; |
benzyl diazoacetate
isochroman-3-one
Conditions | Yield |
---|---|
dirhodium tetraacetate In dichloromethane for 24h; | 56% |
carbon monoxide
phthalyl alcohol
A
isochroman-3-one
B
o-methylphenylacetic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 42h; | A 56% B 9 % Spectr. |
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether; hexane 1) 24 h, room temp. or 4 h reflux; | 53% |
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; palladium diacetate In N,N-dimethyl-formamide at 115℃; for 12h; Inert atmosphere; | 46% |
Conditions | Yield |
---|---|
palladium(II) chloride In water; tert-butyl alcohol | 24% |
α-chloro-α'-cyano-o-xylene
isochroman-3-one
Conditions | Yield |
---|---|
With sodium hydroxide In water at 100℃; for 6h; | 3% |
(2-methoxymethyl-phenyl)-acetonitrile
isochroman-3-one
Conditions | Yield |
---|---|
With hydrogen bromide | |
With sulfuric acid |
Conditions | Yield |
---|---|
With thionyl chloride In 5,5-dimethyl-1,3-cyclohexadiene; N,N-dimethyl-formamide at 20 - 30℃; for 4h; Solvent; | 100% |
With hydrogenchloride at 20 - 26℃; for 2.5h; | 98% |
With thionyl chloride at 20℃; Cooling with ice; | 96% |
chloro-trimethyl-silane
isochroman-3-one
((1H-isochromen-3-yl)oxy)trimethylsilane
Conditions | Yield |
---|---|
Stage #1: isochroman-3-one With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.533333h; Inert atmosphere; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Enzymatic reaction; | 99% |
With n-butyllithium; diisopropylamine 1.) THF, -78 deg C, 10 min, 2.) 3 h, warm. to RT; Yield given. Multistep reaction; |
isochroman-3-one
methylamine
2-(2-(hydroxymethyl)phenyl)-N-methylacetamide
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 8h; | 99% |
In tetrahydrofuran at 20℃; for 8h; | 93% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; | 99% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; | 99% |
With phenylsilane; potassium hydroxide In tetrahydrofuran for 4h; Schlenk technique; Inert atmosphere; Reflux; | 60% |
With samarium diiodide; water In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 65 %Spectr. |
Conditions | Yield |
---|---|
With phosphorus tribromide | 98% |
With hydrogen bromide | 90% |
With hydrogen bromide at 20℃; for 48h; Ring cleavage; esterification; |
isochroman-3-one
methyl 2-(chloromethyl)phenylacetate
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; dichloromethane | 98% |
With thionyl chloride; potassium hydrogencarbonate In methanol; toluene | |
Multi-step reaction with 2 steps 1: thionyl chloride / 4 h / Reflux; Heating 2: 1 h / 20 °C / Cooling with ice View Scheme |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; W(OTf)6; hydrogen; acetic acid at 50℃; under 760.051 Torr; for 12h; | 98% |
With palladium on activated carbon; W(OTf)6; hydrogen In acetic acid at 50℃; under 760.051 Torr; for 12h; | 97% |
Conditions | Yield |
---|---|
With piperidine at 140℃; for 1h; Knoevenagel condensation; | 97% |
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In toluene at 110℃; for 36h; Inert atmosphere; Glovebox; Molecular sieve; Schlenk technique; | 97% |
isochroman-3-one
Conditions | Yield |
---|---|
Stage #1: isochroman-3-one With sodium azide; p-toluenesulfonyl chloride In acetonitrile at 20℃; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; | 96% |
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0℃; | 81% |
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 1h; | 60% |
isochroman-3-one
Methyl formate
methyl (E)-3-methoxy-2-(2-chloromethylphenyl)acrylate
Conditions | Yield |
---|---|
With acetic acid Heating; | 96% |
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In toluene at 110℃; for 36h; Inert atmosphere; Glovebox; Molecular sieve; Schlenk technique; | 95% |
isochroman-3-one
3,4-dihydro-1H-2-benzopyran-3-ol
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In toluene at -60 - -10℃; | 94% |
With diisobutylaluminium hydride In dichloromethane at -78℃; for 3h; | 91% |
With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 1h; Reduction; | |
With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; for 2h; | |
With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h; Inert atmosphere; |
isochroman-3-one
o-(bromomethyl)phenylacetic acid
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid | 93% |
With hydrogen bromide In acetic acid at 20 - 70℃; for 3h; | 93% |
With hydrogen bromide; acetic acid at 70℃; for 1h; | 88% |
With hydrogen bromide In acetic acid 1.) 20 deg C, 2 h; 2.) 70 deg C, 1 h; | |
With hydrogen bromide In water |
isochroman-3-one
3-(3,4-dimethoxyphenyl)propylamine
N-<3-(3,4-Dimethoxyphenyl)propyl><2-(hydroxymethyl)phenyl>acetamid
Conditions | Yield |
---|---|
In ethanol for 3h; Heating; | 92% |
isochroman-3-one
benzylamine
1,4-dihydro-2-(phenylmethyl)-3(2H)-isoquinolinone
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In toluene at 110℃; for 36h; Inert atmosphere; Glovebox; Molecular sieve; Schlenk technique; | 92% |
With aluminium trichloride at 160℃; for 20h; | 73% |
isochroman-3-one
methyl iodide
3,4-dihydro-4-methyl-(3H)-2-benzopyran-3-one
Conditions | Yield |
---|---|
Stage #1: isochroman-3-one With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: methyl iodide at -78℃; for 1h; | 90% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In methanol at 40℃; for 24h; Solvent; Temperature; Concentration; Reagent/catalyst; | 90% |
isochroman-3-one
3-(3-methoxyphenyl)propan-1-amine
Conditions | Yield |
---|---|
In ethanol for 3h; Heating; | 88% |
Conditions | Yield |
---|---|
With heptahydridobis(triphenylphosphine)rhenium In tetrahydrofuran at 150℃; for 5h; Inert atmosphere; teflon-cocked sealed tube; | 88% |
Conditions | Yield |
---|---|
With allyl(cyclopentadiene)palladium(II); 1,3-bis(dicyclohexylphosphine)propane In 1,2-dimethoxyethane at 80℃; for 18h; | 87% |
isochroman-3-one
ethyl cyanoformate
ethyl 3-oxoisochroman-4-carboxylate
Conditions | Yield |
---|---|
Stage #1: isochroman-3-one With lithium diisopropyl amide Inert atmosphere; Stage #2: ethyl cyanoformate Claisen condensation; | 87% |
isochroman-3-one
3-benzyloxy-4-methoxyphenylethylamine
N-<2-(3-benzyloxy-4-methoxyphenyl)-ethyl>-(2-hydroxymethyl)phenylacetamide
Conditions | Yield |
---|---|
In ethanol for 24h; Ambient temperature; | 86% |
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate In toluene at 110℃; for 36h; Inert atmosphere; Glovebox; Molecular sieve; Schlenk technique; | 85% |
The 3H-2-Benzopyran-3-one,1,4-dihydro- with CAS registry number of 4385-35-7 is also known as 3-Isochromanone. The IUPAC name is 1,4-Dihydroisochromen-3-one. It belongs to product categories of Benzopyrans; Building Blocks; Heterocyclic Building Blocks. Its EINECS registry number is 224-493-9. In addition, the formula is C9H8O2 and the molecular weight is 148.16. This chemical is a beige powder that may cause inflammation to the skin or other mucous membranes. It should be sealed in cool, dry place away from oxidants.
Physical properties about 3H-2-Benzopyran-3-one,1,4-dihydro- are: (1)ACD/LogP: 0.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.75; (4)ACD/LogD (pH 7.4): 0.75; (5)ACD/BCF (pH 5.5): 2.19; (6)ACD/BCF (pH 7.4): 2.19; (7)ACD/KOC (pH 5.5): 60.91; (8)ACD/KOC (pH 7.4): 60.91; (9)#H bond acceptors: 2; (10)Index of Refraction: 1.562; (11)Molar Refractivity: 40.16 cm3; (12)Molar Volume: 123.8 cm3; (13)Surface Tension: 43.5 dyne/cm; (14)Density: 1.196 g/cm3; (15)Flash Point: 137.7 °C; (16)Enthalpy of Vaporization: 57.54 kJ/mol; (17)Boiling Point: 332.6 °C at 760 mmHg; (18)Vapour Pressure: 0.000144 mmHg at 25 °C.
Preparation of 3H-2-Benzopyran-3-one,1,4-dihydro-: it is prepared by reaction of 2-methyl-benzyl alcohol. The reaction needs reagent butyllithium and solvents diethyl ether, hexane at room temperature for 24 hours. The yield is about 53%.
Uses of 3H-2-Benzopyran-3-one,1,4-dihydro-: it is used to produce 2-(2-hydroxymethyl-phenyl)-N-(2-indol-3-yl-ethyl)-acetamide by reaction with 2-indol-3-yl-ethylamine. The reaction occurs with solvent ethanol and other condition of heating for 20 hours. The yield is about 83%.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable gloves and eye/face protection. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1C2=CC=CC=C2COC1=O
2. InChI: InChI=1S/C9H8O2/c10-9-5-7-3-1-2-4-8(7)6-11-9/h1-4H,5-6H2
3. InChIKey: ILHLUZUMRJQEAH-UHFFFAOYSA-N
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