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Cas Database

100019-40-7

100019-40-7

Identification

  • Product Name:4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

  • CAS Number: 100019-40-7

  • EINECS:

  • Molecular Weight:245.278

  • Molecular Formula: C14H15NO3

  • HS Code:

  • Mol File:100019-40-7.mol

Synonyms:

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Relevant articles and documentsAll total 1 Articles be found

A new synthesis of flindersine

Anand, R C,Sinha, A K

, p. 560 - 562 (2007/10/02)

Ketene S,N-acetal from the carbethoxylated isobutyl methyl ketone undergoes thermal cyclization with N-phenyl to give 4-hydroxy-3-(3-methylbutanoyl)-2-thiomethylquinoline (III) which is transformed into the corresponding 4-chloro derivative (IV).The carbonyl group in the side chain at 3-position of VI is converted into the α,β-unsaturated ketone (V) followed by acid hydrolysis to afford 4-keto-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyranoquinolin-5-one (VI).Reduction of 4-keto group of VI and subsequent dehydration of the resulting alcohol furnishes flindersine (I).

Process route upstream and downstream products

Process route

4-keto-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-23-9

4-keto-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-24-0,100019-40-7

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

Conditions
Conditions Yield
With ethanol; platinum; Hydrogenation;
With sodium tetrahydroborate; In methanol;
2.4 g
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-24-0,100019-40-7

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 1.) NaH / 1.) DMF, overnight, 2.) DMF, 4 h
2: 75 percent / 1,2-dichloro-benzene / 2 h / Heating
3: 77 percent / Br2 / CHCl3
4: 71 percent / phosphoryl chloride / 4 h / Heating
5: 1.) Br2, 2.) LiBr, Li2CO3 / 1.) glacial acetic acid, 2.) DMF, reflux, 5 h
6: 72 percent / 6N aq. HCl / methanol / 30 h / Heating
7: 2.4 g / NaBH4 / methanol
With hydrogenchloride; sodium tetrahydroborate; bromine; lithium carbonate; sodium hydride; lithium bromide; trichlorophosphate; In methanol; chloroform; 1,2-dichloro-benzene;
4-hydroxy-3-(3-methylbutanoyl)-2-methylmercapto quinoline
135299-36-4

4-hydroxy-3-(3-methylbutanoyl)-2-methylmercapto quinoline

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-24-0,100019-40-7

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 77 percent / Br2 / CHCl3
2: 71 percent / phosphoryl chloride / 4 h / Heating
3: 1.) Br2, 2.) LiBr, Li2CO3 / 1.) glacial acetic acid, 2.) DMF, reflux, 5 h
4: 72 percent / 6N aq. HCl / methanol / 30 h / Heating
5: 2.4 g / NaBH4 / methanol
With hydrogenchloride; sodium tetrahydroborate; bromine; lithium carbonate; lithium bromide; trichlorophosphate; In methanol; chloroform;
4-chloro-3-(3-methylbutanoyl)-2-methylmercaptoquinoline
135299-37-5

4-chloro-3-(3-methylbutanoyl)-2-methylmercaptoquinoline

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-24-0,100019-40-7

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: 1.) Br2, 2.) LiBr, Li2CO3 / 1.) glacial acetic acid, 2.) DMF, reflux, 5 h
2: 72 percent / 6N aq. HCl / methanol / 30 h / Heating
3: 2.4 g / NaBH4 / methanol
With hydrogenchloride; sodium tetrahydroborate; bromine; lithium carbonate; lithium bromide; In methanol;
4-chloro-3-(3-methyl-2-butenoyl)-2-methylmercapto quinoline
135299-38-6

4-chloro-3-(3-methyl-2-butenoyl)-2-methylmercapto quinoline

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-24-0,100019-40-7

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 72 percent / 6N aq. HCl / methanol / 30 h / Heating
2: 2.4 g / NaBH4 / methanol
With hydrogenchloride; sodium tetrahydroborate; In methanol;
2-isopropyl-4-methylmercapto-3(2H)-oxofuro<3,2-e>quinoline
135299-39-7

2-isopropyl-4-methylmercapto-3(2H)-oxofuro<3,2-e>quinoline

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-24-0,100019-40-7

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: 71 percent / phosphoryl chloride / 4 h / Heating
2: 1.) Br2, 2.) LiBr, Li2CO3 / 1.) glacial acetic acid, 2.) DMF, reflux, 5 h
3: 72 percent / 6N aq. HCl / methanol / 30 h / Heating
4: 2.4 g / NaBH4 / methanol
With hydrogenchloride; sodium tetrahydroborate; bromine; lithium carbonate; lithium bromide; trichlorophosphate; In methanol;
ethyl 3-keto-5-methyl-2-<phenylamino(methylmercapto)methenyl>hexanoate
135299-35-3

ethyl 3-keto-5-methyl-2-hexanoate

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-24-0,100019-40-7

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: 75 percent / 1,2-dichloro-benzene / 2 h / Heating
2: 77 percent / Br2 / CHCl3
3: 71 percent / phosphoryl chloride / 4 h / Heating
4: 1.) Br2, 2.) LiBr, Li2CO3 / 1.) glacial acetic acid, 2.) DMF, reflux, 5 h
5: 72 percent / 6N aq. HCl / methanol / 30 h / Heating
6: 2.4 g / NaBH4 / methanol
With hydrogenchloride; sodium tetrahydroborate; bromine; lithium carbonate; lithium bromide; trichlorophosphate; In methanol; chloroform; 1,2-dichloro-benzene;
4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-24-0,100019-40-7

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 1.) NaH / 1.) DMF, overnight, 2.) DMF, 4 h
2: 75 percent / 1,2-dichloro-benzene / 2 h / Heating
3: 77 percent / Br2 / CHCl3
4: 71 percent / phosphoryl chloride / 4 h / Heating
5: 1.) Br2, 2.) LiBr, Li2CO3 / 1.) glacial acetic acid, 2.) DMF, reflux, 5 h
6: 72 percent / 6N aq. HCl / methanol / 30 h / Heating
7: 2.4 g / NaBH4 / methanol
With hydrogenchloride; sodium tetrahydroborate; bromine; lithium carbonate; sodium hydride; lithium bromide; trichlorophosphate; In methanol; chloroform; 1,2-dichloro-benzene;
4-keto-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-23-9

4-keto-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-24-0,100019-40-7

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

Conditions
Conditions Yield
With ethanol; platinum; Hydrogenation;
With sodium tetrahydroborate; In methanol;
2.4 g
phenyl isothiocyanate
103-72-0

phenyl isothiocyanate

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one
91794-24-0,100019-40-7

4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one

Conditions
Conditions Yield
Multi-step reaction with 7 steps
1: 1.) NaH / 1.) DMF, overnight, 2.) DMF, 4 h
2: 75 percent / 1,2-dichloro-benzene / 2 h / Heating
3: 77 percent / Br2 / CHCl3
4: 71 percent / phosphoryl chloride / 4 h / Heating
5: 1.) Br2, 2.) LiBr, Li2CO3 / 1.) glacial acetic acid, 2.) DMF, reflux, 5 h
6: 72 percent / 6N aq. HCl / methanol / 30 h / Heating
7: 2.4 g / NaBH4 / methanol
With hydrogenchloride; sodium tetrahydroborate; bromine; lithium carbonate; sodium hydride; lithium bromide; trichlorophosphate; In methanol; chloroform; 1,2-dichloro-benzene;

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