485-51-8

Basic information

• Product Name: Corlumine
• Synonyms: Corlumine;(6R)-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: 485-51-8
• Molecular Formula: C21H21NO6
• Molecular Weight: 383.43
• Mol File: 485-51-8.mol
• Article Data: 7

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: Corlumine(CAS DataBase Reference)
• NIST Chemistry Reference: Corlumine(485-51-8)
• EPA Substance Registry System: Corlumine(485-51-8)

Safety Data

• Hazardous Substances Data: 485-51-8(Hazardous Substances Data)

Usage

Uses

Agricultural chemical.

Hazard

A poison.

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-/m1/s1

Upstream product

• 50-00-0 formaldehyd 
• 124-38-9 carbon dioxide 
• 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 
• 58343-48-9 5-formyl-benzo[1,3]dioxole-4-carboxylic acid 
• 247579-61-9 1-[2-bromo-3,4-(methylenedioxy)benzoyl]-6,7-dimethoxy-3,4-dihydroisoquinoline 
• 247579-54-0 N-(3,4-dimethoxyphenethyl)-2-bromo-3,4-(methylenedioxy)phenylacetamide 
• 247579-57-3 1-[2-bromo-3,4-(methylenedioxy)benzyl]-6,7-dimethoxy-3,4-dihydroisoquinoline 
• 247579-52-8 2-bromo-3,4-(methylenedioxy)phenylacetic acid 
• 247579-53-9 (4-bromo-benzo[1,3]dioxol-5-yl)-acetyl chloride 
• 247579-50-6 2-bromo-3,4-(methylenedioxy)benzyl alcohol 
• 247579-51-7 2-bromo-3,4-(methylenedioxy)phenylacetonitrile 
• 168776-08-7 4-bromo-5-chloromethyl-benzo[1,3]dioxole 
• 56008-63-0 4-bromobenzo[d][1,3]dioxole-5-carbaldehyde 
• 201230-82-2 carbon monoxide 

Downstream Products

• 79082-64-7 (+)-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.

EPC-synthesis of tetrahydroisoquinolines by diastereoselective alkylation at the 1-position of phenylalanine-derived precursors. Synthesis of the alkaloid (+)-corlumine

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