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54879-83-3

54879-83-3

Identification

Synonyms:N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine

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Relevant articles and documentsAll total 5 Articles be found

Synthesis of 1,2-Dihydroisoquinolines by a Modified Pomeranz-Fritsch Cyclization

Ji, Xiang,Huang, Zheng,Lumb, Jean-Philip

, p. 1062 - 1072 (2020/01/31)

Isoquinolines (IQs) and their derivatives are present in many natural products and biologically active small molecules. Herein, we report a modified procedure for the classical Pomeranz-Fritsch protocol, which expands the scope of 1,2-dihydroisoquinoline (DHIQ) products. 1,2-DHIQs are an attractive branch point for the synthesis of IQs, but because of their innate reactivity, they have remained difficult to prepare. We demonstrate that the Fujioka/Kita conditions, combining trimethylsiyltriflate (TMSOTf) and an amine base, activate dimethylacetals required for Pomeranz-Fritsch cyclization under sufficiently mild conditions to prepare a broad range of 1,2-DHIQ products. We also demonstrate the synthetic value of these DHIQs by further functionalization to either reduced tetrahydroisoquinoline (THIQ) or fully aromatized IQ natural products.

Synthesis of Indenoisoquinoliniums and Methods of Use

-

Page/Page column 11-12, (2008/12/07)

Substituted indenoisoquinolinium compounds, and pharmaceutical formulations of substituted indenoisoquinolinium compounds are described. Also described are processes for preparing substituted indenoisoquinolinium compounds. Also described are methods for

Synthesis and mechanism of action studies of a series of norindenoisoquinoline topoisomerase I poisons reveal an inhibitor with a flipped orientation in the ternary DNA-enzyme-inhibitor complex as determined by X-ray crystallographic analysis

Ioanoviciu, Alexandra,Antony, Smitha,Pommier, Yves,Staker, Bart L.,Stewart, Lance,Cushman, Mark

, p. 4803 - 4814 (2007/10/03)

Several norindenoisoquinolines substituted with methoxy or methylenedioxy groups have been prepared and their anticancer properties evaluated in cancer cell cultures and in topoisomerase I inhibition assays. 2,3-Dimethoxy-8,9- methylenedioxy-11H-indeno[1,

Preparation of N-benzylsulfonamido-1,2-dihydroisoquinolines and their reaction with Raney nickel. A mild, new synthesis of isoquinolines

Larghi, Enrique L.,Kaufman, Teodoro S.

, p. 3159 - 3162 (2007/10/03)

N-benzylsulfonamido-1,2-dihydroisoquinolines react with Raney nickel to provide isoquinotines in excellent yields and under mild, neutral conditions.

Studies Directed Towards Total Syntheses of the Tropoloisoquinoline Alkaloids Grandirubrine and Imerubrine. I. Preparation of Two 4,5,6-Trimethoxycyclopentisoquinolin-7-ones and Their Response to Robinson Annulation Conditions

Banwell, Martin G.,Bonadio, Anna,Turner, Kathleen A.,Ireland, Neil K.,Mackay, Maureen F.

, p. 325 - 351 (2007/10/02)

In connection with efforts to develop total syntheses of the tropoloisoquinoline alkaloids grandirubrine (1) and imerubrine (2), preparations of tricyclic ketone (8) and the related ethoxycarbonyl system (47) are described.Of the various approaches to (8)

Process route upstream and downstream products

Process route

2,2-dimethoxy-N-<(3',4',5'-trimethoxyphenyl)methylene>ethylamine
39964-85-7

2,2-dimethoxy-N-<(3',4',5'-trimethoxyphenyl)methylene>ethylamine

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine
54879-83-3

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine

Conditions
Conditions Yield
With hydrogen; platinum(IV) oxide; In ethanol; for 2.5h; under 760 Torr;
100%
With sodium tetrahydroborate; In ethanol; Heating;
100%
2,2-dimethoxy-N-<(3',4',5'-trimethoxyphenyl)methylene>ethylamine; With sodium tetrahydroborate; In methanol; at 20 - 80 ℃; for 24h;
With water; In chloroform;
100%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine
54879-83-3

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 100 percent / MgSO4 / CHCl3 / 24 h / 20 °C
2: 100 percent / NaBH4 / ethanol / Heating
With sodium tetrahydroborate; magnesium sulfate; In ethanol; chloroform;
Multi-step reaction with 2 steps
1: 100 percent / benzene / 5.25 h / Heating
2: 100 percent / hydrogen / platinum(IV) oxide / ethanol / 2.5 h / 760 Torr
With hydrogen; platinum(IV) oxide; In ethanol; benzene;
Multi-step reaction with 2 steps
1: magnesium sulfate / chloroform / 24 h / 20 °C
2: sodium tetrahydroborate / methanol / 24 h / 20 - 80 °C
With sodium tetrahydroborate; magnesium sulfate; In methanol; chloroform;
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

2,2-dimethoxyethylamine
22483-09-6

2,2-dimethoxyethylamine

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine
54879-83-3

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine

Conditions
Conditions Yield
With sodium cyanoborohydride; acetic acid; In ethanol; Yield given; Heating;
3,4,5-trimethoxy-benzaldehyde; 2,2-dimethoxyethylamine; With acetic acid; In methanol; at 20 ℃; for 2h;
With sodium tetrahydroborate; In water; at 20 ℃; for 12h;
N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine
54879-83-3

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine

Conditions
Conditions Yield
2j, H2; (S.2188);
N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine
54879-83-3

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-(2'',2''-dimethoxyethyl)-4-methyl-N-(3''',4''',5'''-trimethoxyphenylmethyl)benzene sulfonamide
39964-89-1

N-(2'',2''-dimethoxyethyl)-4-methyl-N-(3''',4''',5'''-trimethoxyphenylmethyl)benzene sulfonamide

Conditions
Conditions Yield
With pyridine; for 72h; Ambient temperature;
94%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine
54879-83-3

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine

N-(2,2-dimethoxyethyl)-1,1,1-trifluoro-N-(3,4,5-trimethoxybenzyl)methanesulfonamide

N-(2,2-dimethoxyethyl)-1,1,1-trifluoro-N-(3,4,5-trimethoxybenzyl)methanesulfonamide

Conditions
Conditions Yield
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 20 ℃; for 1h;
3.08 g
N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine
54879-83-3

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine

5,6,7-Trimethoxy-2-phenylmethanesulfonyl-1,2-dihydro-isoquinoline
191112-98-8

5,6,7-Trimethoxy-2-phenylmethanesulfonyl-1,2-dihydro-isoquinoline

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 2 M Na2CO3 / toluene / Ambient temperature
2: aq. 6 N HCl / dioxane / 0.33 h / Heating
With hydrogenchloride; sodium carbonate; In 1,4-dioxane; toluene;
N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine
54879-83-3

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine

ethyl 2-benzoyl-1-cyano-5,6,7-trimethoxy-1,2-dihydroisoquinoline-8-carboxylate
148492-77-7

ethyl 2-benzoyl-1-cyano-5,6,7-trimethoxy-1,2-dihydroisoquinoline-8-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: 94 percent / pyridine / 72 h / Ambient temperature
2: 76 percent / 6 M aq. HCl / dioxane / 24 h / Heating
3: 76 percent / N-bromosuccinimide / tetrahydrofuran / 3 h / Ambient temperature
4: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, 20 min
5: 89 percent / CH2Cl2; H2O / 22.5 h / Ambient temperature
With pyridine; hydrogenchloride; N-Bromosuccinimide; n-butyllithium; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;
N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine
54879-83-3

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine

ethyl 2-benzoyl-1-cyano-5,6,7-trimethoxy-1-methyl-1,2-dihydroisoquinoline-8-carboxylate
148492-78-8

ethyl 2-benzoyl-1-cyano-5,6,7-trimethoxy-1-methyl-1,2-dihydroisoquinoline-8-carboxylate

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: 94 percent / pyridine / 72 h / Ambient temperature
2: 76 percent / 6 M aq. HCl / dioxane / 24 h / Heating
3: 76 percent / N-bromosuccinimide / tetrahydrofuran / 3 h / Ambient temperature
4: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, 20 min
5: 89 percent / CH2Cl2; H2O / 22.5 h / Ambient temperature
6: 99 percent / sodium hydride / dimethylformamide / 7 h / Ambient temperature
With pyridine; hydrogenchloride; N-Bromosuccinimide; n-butyllithium; sodium hydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine
54879-83-3

N-(2'',2''-dimethoxyethyl)-3',4',5'-trimethoxyphenylmethylamine

ethyl 2-benzoyl-1-cyano-8-ethoxycarbonyl-5,6,7-trimethoxy-1,2-dihydroisoquinoline-1-ethanoate
148492-83-5

ethyl 2-benzoyl-1-cyano-8-ethoxycarbonyl-5,6,7-trimethoxy-1,2-dihydroisoquinoline-1-ethanoate

Conditions
Conditions Yield
Multi-step reaction with 6 steps
1: 94 percent / pyridine / 72 h / Ambient temperature
2: 76 percent / 6 M aq. HCl / dioxane / 24 h / Heating
3: 76 percent / N-bromosuccinimide / tetrahydrofuran / 3 h / Ambient temperature
4: 1.) butyllithium / 1.) hexane, THF, -78 deg C, 15 min, 2.) hexane, THF, 20 min
5: 89 percent / CH2Cl2; H2O / 22.5 h / Ambient temperature
6: 99 percent / sodium hydride / dimethylformamide / 16 h / Ambient temperature
With pyridine; hydrogenchloride; N-Bromosuccinimide; n-butyllithium; sodium hydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

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