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5-nitro-2-((trifluoromethyl)thio)isoindoline-1,3-dione[ No CAS ]
[ 768-03-6 ]
5-nitro-2-(3-oxo-3-phenyl-2-((trifluoromethyl)thio)propyl)isoindoline-1,3-dione[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
84%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
84%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
2 Example 25-nitro-2- (3-oxo-3-phenyl (trifluoromethylthio) -2- propyl) isoindoline-1,3-dione (formula below) synthesized:
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- phenyl-2-propenyl-1-one (19.8mg, 0.15mmol), 1, mixture of the 4-diazabicyclo [2.2.2] octane (DBACO) (8.75mg, 0.075mmol) and acetonitrile (0.45 mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography to obtain the product isolated in 84% yield.
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
87%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
4 Example 4 synthesis of: 5-nitro-2- (3-oxo-3-p-methoxyphenyl-2- (trifluoromethylthio) propyl) isoindoline-1,3-dione
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- p-methoxyphenyl-2-propenyl-1-one (24.3mg, 0.15mmol ), a mixture of 1,4-diazabicyclo [2.2.2] octane (DBACO) (8.75mg, 0.075mmol) and acetonitrile (0.45 mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography to obtain the product isolated in 87% yield.
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
83%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
5 Example 5 Synthesis of :5-nitro-2- (3-oxo-3-trifluoromethyl-phenyl-2- (trifluoromethylthio) propyl) isoindoline-1,3-dione (formula below)
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- trifluoromethyl-phenyl-2-propenyl-1-one (30mg, 0.15mmol ), a mixture of 1,4-diazabicyclo [2.2.2] octane (DBACO) (8.75mg, 0.075mmol) and acetonitrile (0.45 mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography to obtain the product isolated in 83% yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
88%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
6 Example 6 Synthesis of -5-nitro-2- (3-oxo-3-p-fluoro-2- (trifluoromethylthio) propyl) isoindoline-1,3-dione (chemical formula shown below)
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- p-fluorophenyl-2-propenyl-1-one (22.5mg, 0.15mmol), mixture of 1,4-diazabicyclo [2.2.2] octane (DBACO) (8.75 mg, 0.075mmol) and acetonitrile (0.45 mL) is stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography to obtain the product isolated in 88% yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
92%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
7 Example 7 Synthesis:-5-nitro-2- (3-oxo-3-p-chlorophenyl-2- (trifluoromethylthio) propyl) isoindoline-1,3-dione (chemical formula shown below)
- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- p-chlorophenyl-2-propenyl-1-one (24.9mg, 0.15mmol), mixture of 1,4-diazabicyclo [2.2.2] octane (DBACO) (8.75 mg, 0.075mmol) and acetonitrile (0.45 mL) is stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography, the product isolated in 92% yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
89%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
8 Example 8 Synthesis:-5-nitro-2- (3-oxo-3-p-bromo-2- (trifluoromethylthio) propyl) isoindoline-1,3-dione (chemical formula shown below)
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- p-bromophenyl-2-propenyl-1-one (31.5mg, 0.15mmol), mixture of 1,4-diazabicyclo [2.2.2] octane (DBACO) (8.75 mg, 0.075mmol) and acetonitrile (0.45 mL) is stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography to obtain the product isolated in 89% yield.
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
87%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
9 EXAMPLE 9 synthesis:-5-nitro-2- (3-oxo-3-m-methoxyphenyl-2- (trifluoromethylthio) propyl) isoindoline-1,3-dione (formula below)
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- m-methoxyphenyl-2-propenyl-1-one (24.3mg, 0.15mmol ), a mixture of 1,4-diazabicyclo [2.2.2] octane (DBACO) (8.75mg, 0.075mmol) and acetonitrile (0.45 mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography to obtain the product isolated in 87% yield.
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
85%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
12 Example 12 Synthesis:-5-nitro-2- (3-oxo-3-o-chlorophenyl-2- (trifluoromethylthio) propyl) isoindoline-1,3-dione (chemical formula shown below)
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- o-chlorophenyl-2-propenyl-1-one (24.9mg, 0.15mmol), mixture of 1,4-diazabicyclo [2.2.2] octane (DBACO) (8.75 mg, 0.075mmol) and acetonitrile (0.45 mL) is stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography to obtain the product isolated in 85% yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
86%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
13 Example 13Synthesis ;-5-nitro-2-(3-oxo-3-1'-naphthyl-2-(trifluoromethylthio)propyl)isoindoline-1,3-dione(formula shown below)
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- naphthyl-2-propenyl-1-one (27.3mg, 0.15mmol), 1, mixture of the 4-diazabicyclo [2.2.2] octane (DBACO) (8.75mg, 0.075mmol) and acetonitrile (0.45 mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography, the product isolated in 86% yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
89%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
14 Example 14 Synthesis:-5-nitro-2- (3-oxo-2--3-3'- (trifluoromethylthio) propyl) isoindoline-1,3-dione (formula shown below)
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1-3'- furan-2-propenyl-1-one (18.3mg, 0.15mmol), mixture of 1,4-diazabicyclo [2.2.2] octane (DBACO) (8.75 mg, 0.075mmol) and acetonitrile (0.45 mL) is stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography to obtain the product isolated in 89% yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
88%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
15 Example 15 synthesized;-5-nitro-2- (3-oxo-3-cyclohexyl-2- (trifluoromethylthio) propyl) isoindoline-1,3-dione (formula below)
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- cyclohexyl-2-propenyl-1-one (20.7mg, 0.15mmol), 1, mixture of the 4-diazabicyclo [2.2.2] octane (DBACO) (8.75 mg, 0.075mmol) and acetonitrile (0.45 mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography to obtain the product isolated in 88% yield
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
80%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
16 Example 16 synthesized:- 5-nitro-2- (3-oxo-5-phenyl-2- (trifluoromethylthio) pentyl) isoindoline-1,3-dione (formula below)
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 5- phenyl-1-penten-3-one (24.0mg, 0.15mmol), 1, mixture of the 4-diazabicyclo [2.2.2] octane (DBACO) (8.75mg, 0.075mmol) and acetonitrile (0.45 mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure, column chromatography, the product isolated in 80% yield.
5-nitro-2-((trifluoromethyl)thio)isoindoline-1,3-dione[ No CAS ]
phenyl 3-(5-nitro-1,3-dioxoisoindolin-2-yl)-2-((trifluoromethyl)thio)propanoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
80%
With 1,4-diaza-bicyclo[2.2.2]octane; In 1,4-dioxane; dichloromethane; at 20℃; for 40h;
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- acrylate, phenyl (22.2mg, 0.15mmol), DABCO (8.75mg, 0.075mmol) and di a mixed solution of methylene chloride and 1,4-dioxane: mixture (volume ratio 1 1,0.45mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure, by column chromatography to give product 1- (4-nitro-phthalimide) -2-trifluoromethylthio - phenyl propionate, 80% isolated yield.
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
71%
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
20 Example 202-trifluoromethyl-1- (4-nitro-phthalimide) - propionic acid naphthyl ester (chemical formula below):
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- naphthyl acrylate ester (29.7mg, 0.15mmol), DABCO (8.75mg, 0.075mmol) and di a mixed solution of methylene chloride and 1,4-dioxane: mixture (volume ratio 1 1,0.45mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure column chromatography to obtain the product isolated in 71% yield.
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
54%
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
21 Example 212-trifluoromethyl-1- (4-nitro-phthalimide) - propionic acid benzyl ester
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- benzyl acrylate (24.3mg, 0.15mmol), DABCO (8.75mg, 0.075mmol) and di a mixed solution of methylene chloride and 1,4-dioxane: mixture (volume ratio 1 1,0.45mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure column chromatography to obtain the product isolated in 54% yield.
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
45%
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
22 Example 22 synthesized;- 2-trifluoromethyl-1- (4-nitro-phthalimide) - propionic acid ethyl ester (chemical formula below)
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- ethyl acrylate (15mg, 0.15mmol), DABCO (8.75mg, 0.075mmol) and dichlorobis methane with a mixed solution of 1,4-dioxane: mixture (volume ratio 1 1,0.45mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure column chromatography to obtain the product isolated in 45% yield.
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
54%
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
23 Example 232-trifluoromethyl-1- (4-nitro-phthalimide) - propionic acid ester
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- butyl acrylate (19.2mg, 0.15mmol), DABCO (8.75mg, 0.075mmol) and di a mixed solution of methylene chloride and 1,4-dioxane: mixture (volume ratio 1 1,0.45mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure column chromatography to obtain the product isolated in 54% yield.
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
79%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 40h;
25 Example 25 2-trifluoromethyl-methylthio-3- (4-nitro-phthalimide) - propionic acid propargyl
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- propargyl acrylate (16.5mg, 0.15mmol), DABCO (8.75mg, 0.075mmol) and a mixed solution of methylene chloride and 1,4-dioxane: mixture (volume ratio 1 1,0.45mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure column chromatography to obtain the product isolated in 79% yield
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
36%
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
26 Example 26 synthesized: 2-trifluoromethyl-methylthio-3- (4-nitro-phthalimide) - propionitrile (chemical formula below)
N- trifluoromethylthio-4-nitro phthalimide (131.4mg, 0.45mmol), acrylonitrile (15.9 mg, 0.30mmol), DABCO (17.5mg, 0.15mmol) and methylene chloride with a mixed solution of 1,4-dioxane: mixture (volume ratio 1 1,0.9mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure column chromatography product was isolated in 36% yield.
Synthesis of N- trifluoromethylthio-4-nitro-o-phthalimido ammonia reagent
Under nitrogen, N- chloro-4-nitro phthalimide (2.26g, 10mmol), the mixture was trifluoromethylthio silver (2.70g, 13mmol) and acetonitrile (20 mL) was stirred at room temperature for 3 hours .Concentrated under reduced pressure, filtered through Celite to give a white solid with a yield of 95%.
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; dichloromethane at 20℃; for 40h;
24 Example 242-trifluoromethyl-1- (4-nitro-phthalimide) - propanoic acid cinnamyl ester
N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- cinnamyl acrylate (28.2mg, 0.15mmol), DABCO (8.75mg, 0.075mmol) and di a mixed solution of methylene chloride and 1,4-dioxane: mixture (volume ratio 1 1,0.45mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure column chromatography to obtain the product isolated in 76% yield.
5
The synthesis steps and process are: add 4-phenylbenzoic acid trifluoromethyl thioester 3a (0.4 mmol, 112.8 mg), tetrabutylammonium fluoride (0.5 mmol, 130.5 mg), 3 mL benzotrifluoride, mix well and add 2-chloro-5-nitroisoindoline-1,3-dione 2e (0.4 mmol, 90.6 mg); fix the reaction tube on a magnetic stirrer , Reacted at 25°C for 12 hours, and then separated and purified to obtain the target product 1b with a yield of 56%.
With potassium fluoride; 18-crown-6 ether at 30℃; for 6h;
4
The synthesis steps and process are: add 4-phenylbenzoic acid trifluoromethyl thioester 3a (0.4 mmol, 112.8 mg), potassium fluoride (0.6 mmol, 34.8 mg), 18-Crown ether-6 (1.0 mmol, 264 mg), 4.0 mL of benzotrifluoride, 2-bromo-5-nitroisoindoline-1,3-dione 2d (0.45 mmol, 122.0 mg); The tube was fixed on a magnetic stirrer and reacted at 30°C for 6 hours. After the completion of separation and purification, the target product was obtained with a yield of 55%.
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