524-46-9

Basic information

• Product Name: [6S,(+)]-6-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one
• Synonyms: [6S,(+)]-6-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one
• CAS NO: 524-46-9
• Molecular Formula: C21H21NO6
• Molecular Weight: 383.3945
• Mol File: 524-46-9.mol

Chemical Properties

• Boiling Point: 542.1°Cat760mmHg
• Flash Point: 281.6°C
• Appearance: /
• Density: 1.339g/cm³
• Vapor Pressure: 8.17E-12mmHg at 25°C
• Refractive Index: 1.614
• CAS DataBase Reference: [6S,(+)]-6-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: [6S,(+)]-6-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one(524-46-9)
• EPA Substance Registry System: [6S,(+)]-6-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one(524-46-9)

Safety Data

• Hazardous Substances Data: 524-46-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
[6S,(+)]-6-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one is used as a potential pharmaceutical candidate for [application reason] due to its complex chemical structure and potential pharmacological properties.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, [6S,(+)]-6-[(1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one is used as a subject of study for [application reason] because of its intriguing molecular architecture and the possibility of discovering new therapeutic agents based on its structure.

InChI:InChI=1/C21H21NO6/c1-22-7-6-11-8-15(24-2)16(25-3)9-13(11)18(22)19-12-4-5-14-20(27-10-26-14)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19-/m0/s1

Upstream product

• 13168-51-9 N-benzoyl-norreticuline 
• 1699-46-3 reticuline 
• 485-19-8 (R)-reticuline 
• 21414-43-7 l-adlumidine 
• 64361-55-3 6-((E)-6,7-dimethoxy-2-methyl-3,4-dihydro-2H-isoquinolin-1-ylidene)-6H-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-8-one 
• 30045-07-9 2-methyl-6,7-dimethoxy-3,4-dihydroisoquinolinium iodide 
• 125239-01-2 Potassium; 8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxole-6-carboxylate 
• 80053-50-5 6,7-methylenedioxy-3-chlorophthalide 
• 201230-82-2 carbon monoxide 
• 58343-48-9 5-formyl-benzo[1,3]dioxole-4-carboxylic acid 
• 64395-09-1 8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxole-6-carboxylic acid (3,4-dimethoxy-phenethyl)-methyl-amide 
• 124-38-9 carbon dioxide 
• 56008-63-0 4-bromobenzo[d][1,3]dioxole-5-carbaldehyde 
• 168776-08-7 4-bromo-5-chloromethyl-benzo[1,3]dioxole 

Downstream Products

• 485-51-8 (+/-)-adlumine 
• 79082-64-7 (+)-corlumine 
• 485-51-8 (+)-corlumine 

Relevant articles and documents

Synthesis of phthalideisoquinoline and protoberberine alkaloids and indolo[2,1-α]isoquinolines in a divergent route involving palladium(0)- catalyzed carbonylation

6,7,3',4'-Alkoxy-substituted 1-(2'-bromobenzoyl)-3,4-dihydroisoquinoline methiodides 17 were treated with sodium borohydride in methanol or acetic acid to give erythro-1-(2'-bromo-α-hydroxybenzyl)-2-methyl-1,2,3,4- tetrahydroisoquinolines 19. Treatment of 17 with lithium aluminum hydride in tetrahydrofuran gave the threo-isomer 20 in preference to the erythro 19. On the basis of studies on palladium(0)-catalyzed carbonylation of 2-bromo-3,4- dimethoxybenzyl alcohol to 6,7-dimethoxyphthalide, amino alcohol 19 or 20 was treated with a catalytic amount of palladium(II) acetate and triphenylphosphine in an atmosphere of carbon monoxide in the presence of chlorotrimethylsilane and potassium carbonate in boiling toluene to give the corresponding erythro- or threo-types of phthalideisoquinoline alkaloids 1 or 2, respectively. One-pot cyclization of the erythro-amino alcohols 19 was achieved by heating in N,N-dimethylformamide containing potassium carbonate to give 2,3,8,9- or 2,3,9,10-alkoxy-substituted 5,6-dihydroindolo[2,1- α]isoquinolines 3, which have a unique tetracyclic skeleton characteristic of dibenzopyrrocoline alkaloids. Similarly, palladium-(0)-catalyzed carbonylation of 1-(2'-bromobenzyl)tetrahydroisoquinolines 21 in the presence of excess potassium carbonate was found to give 8-oxoberbines 22, which on reduction with lithium aluminum hydride can be converted to protoberberine alkaloids 4.

Studies on Carboxylation of Alkoxy-Substituted Benzyl Alcohols via Direct Lithiation and Bromine-Lithium Exchange: Synthesis of Phthalides and Phthalideisoquinoline Alkaloids

Conversion of alkoxy-substituted benzyl alcohols to the corresponding phthalides by carboxylation via ortho lithiation and bromine-lithium exchange was studied.The method was applied to the key step in the synthesis of phthalideisoquinoline alkaloids.

A FACILE SYNTHESIS OF PHTHALIDEISOQUINOLINES BY DECARBOXYLATION OF PHTHALIDECARBOXYLATES IN THE PRESENCE OF IMINE METHIODIDES

Decarboxylation of potassium phthalide-3-carboxylates in the presence of acyclic imine methiodides in DMSO leads mainly to 2-acylbenzamides, but with 3,4-dihydroisoquinolinium methiodides, a one step synthesis of phthalideisoquinolines is achieved in mode

THE BIOSYNTHESIS OF THE ALKALOIDS OF CORYDALIS MEIFOLIA WALL.

Tracer experiments show that corlumine, cavidine and yenhusomine are stereospecifically biosynthesized from (R)-(-)-reticuline.

Synthesis of phthalideisoquinolines from 3-halophthalides and 3,4-dihydroisoquinolinium salts

Phthalideisoquinoline alkaloids have been synthesized by coupling appropriately substituted 3-halophthalides and 2-methyl-3,4-dihydroisoquinolinium salts in the presence of Zn(Cu) couple or metallic Zn.Both erythro and threo isomers are formed in the reaction.The nmr spectra of the (+/-)-erythro- and (+/-)-threo-isocordrastines have been reinvestigated.The results, which differ from those previously reported, lead to a different conclusion regarding the conformations of the molecules.