4356-47-2

Usage

InChI:InChI=1/C12H17NO3/c1-15-11-5-8-3-4-13-10(7-14)9(8)6-12(11)16-2/h5-6,10,13-14H,3-4,7H2,1-2H3/p+1/t10-/m1/s1

Upstream product

• 147624-55-3 4-(1-(N-(2,2-diethoxyethyl)amino)-2-(benzyloxy)ethyl)-1,2-dimethoxybenzene 
• 38485-01-7 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid hydrochloride 
• 1370371-80-4 N-(2,2-diethoxyethyl)-α-(3,4-dimethoxyphenyl)glycine 
• 1370371-81-5 N-(2,2-dimethoxyethyl)-N-benzyl-α-(3,4-dimethoxyphenyl)glycine 
• 1370371-82-6 N-(2,2-dimethoxyethyl)-α-(3,4-dimethoxyphenyl)glycine 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 13326-57-3 ethyl 6,7-dimethoxy-3,4-dihydroisoquinoline-1-carboxylate 
• 14022-16-3 (2-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methanol 
• 124201-24-7 1-formyl-4,5-dimethoxyphenylacetic acid methyl ester 
• 88387-98-8 [2-(3,4-Dimethoxy-phenyl)-ethylcarbamoyloxy]-acetic acid ethyl ester 
• 21997-97-7 3-(3,4-dimethoxy-phenyl)-propionyl azide 
• 2107-70-2 3,4-methoxycinnamic acid 
• 93631-45-9 6,7-Dimethoxy-2-ethoxycarbonyl-1,2-dihydroisoquinaldonitrile 
• 15248-39-2 6,7-dimethoxyisoquinoline 

Downstream Products

• 93598-34-6 (+/-)-N-methylcalycotomine 
• 1308338-95-5 (S)-(2-(2-fluorobenzyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)(1-(hydroxymethyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone 
• 1308338-32-0 (S)-(2-(2-fluorobenzyl)-1,2,3,4-tetrahydroisoquinolin-3-yl)(1-(hydroxymethyl)-6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)methanone 
• 109717-72-8 (-)-threo-N-(ethoxycarbonyl)hydroxynorlaudanosine 
• 109717-73-9 (S)-3,4-dimethoxyphenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl-methanol 
• 6872-27-1 (R)-(+)-xylopinine 
• 486-99-7 (S)-1-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 87496-35-3 1-Hydroxymethyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbothioic acid cyclohexylamide 
• 87496-32-0 1-Hydroxymethyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbothioic acid phenylamide 
• 98979-80-7 8,9-dimethoxy-3-phenyl-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinoline 

Relevant academic research and scientific papers

Approach to Isoindolinones, Isoquinolinones, and THIQs via Lewis Acid-Catalyzed Domino Strecker-Lactamization/Alkylations

A one-pot, three-component synthesis of widely substituted isoindolinones and isoquinolinones, featuring a Lewis acid-catalyzed efficient Strecker reaction and lactamization sequence, affording products in good to high yields is reported. The method has also been extended to the synthesis of tetrahydroisoquinolines (THIQs) in high yields. (Chemical Equation Presented).

A concise synthesis of tetrahydroisoquinoline-1-carboxylic acids using a Petasis reaction and Pomeranz-Fritsch-Bobbitt cyclization sequence

A sequence of two reactions: the Petasis reaction, in which an aminoacetaldehyde acetal was used as the amine component, followed by Pomeranz-Fritsch-Bobbitt cyclization, has been shown to be a convenient and simple method for the synthesis of tetrahydroisoquinoline-1-carboxylic acids. Using this method several acids have been prepared in good to excellent yields and characterized as hydrochloride salts.

Synthesis and conformational analysis of tetrahydroisoquinoline- and piperidine-fused 1,3,4,2-oxadiazaphosphinanes, new ring systems

Through cyclization of tetrahydroisoquinoline and piperidine 1,2-hydrazino alcohols with phenylphosphonic dichloride and phenyl dichlorophosphate, P-epimeric diastereomers of 1,6,7,11b-tetrahydro-4H-1,3,4,2-oxadiazaphosphino[5, 4-a]isoquinoline-3-oxides (

Pictet-Spengler condensation of N-sulfonyl-β-phenethylamines with α- chloro-α-phenylselenoesters. New synthesis of 1,2,3,4- tetrahydroisoquinoline-1-carboxylates

The reaction of N-sulfonyl-β-phenethylamines with α-chloro-a- phenylseleno acetate/propionate esters under Lewis acid promotion gives moderate to good yields of the corresponding 1,2,3, 4- tetrahydroisoquinoline-1-carboxylates. Varying degrees of diastereoselection were obtained using chiral sulfonamides and/or esters. Employing this strategy, the achievement of a new total synthesis of Calycotomine is reported.

Reduction and carboxylation of 1-chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinolinLum salts. An easy entry to 1-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline alkaloids

At 25°C, the NaBH4/MeOH reduction of the title isoquinolinium salts gave the aziridine exclusively. At a low temperature (0°C) in the presence of CO2/K2CO3, the 2-oxazolidinone was obtained in almost quantitative yield. Controlled hydrolysis of the borane complex derived from the isoquinolinium salts also gave the cyclic carbamate. (±)-Calycotomine and its N-Me derivative were obtained in high yields.

Extension of the Bobbitt acetal cyclization to the elaboration of 1-hydroxymethyl-substituted simple tetrahydroisoquinolines. A new synthesis of calycotomine

Aromatic benzyloxymethyl ketones are convenient intermediates for the elaboration, via the Bobbitt acetal cyclization, of 1-hydroxymethyl-substituted simple tetrahydroisoquinolines, such as calycotomine and one bearing the 1,7,8-oxygenated substitution pa

THE SYNTHESIS OF THE ISOQUINOLINE ALKALOID CALYCOTOMINE VIA FUNCTIONALIZATION OF ENAMIDE DOUBLE BONDS

The novel alkaloid calycotomine, a 1-hydroxymethylenetetrahydroisoquinoline, has been synthesized from 1-methyl-3,4-dihydroisoquinoline via the 2-benzyloxycarbonyl enamide derivative.Oxidation of the enamide with osmium tetroxide results in bis-hydroxylat