38184-69-9

Basic information

• Product Name: Adlumine
• Synonyms: Adlumine
• CAS NO: 38184-69-9
• Molecular Formula: C21H21NO6
• Molecular Weight: 383.39454
• Mol File: 38184-69-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Adlumine(CAS DataBase Reference)
• NIST Chemistry Reference: Adlumine(38184-69-9)
• EPA Substance Registry System: Adlumine(38184-69-9)

Safety Data

• Hazardous Substances Data: 38184-69-9(Hazardous Substances Data)

Upstream product

• 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 
• 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 
• 124-38-9 carbon dioxide 
• 30045-07-9 2-methyl-6,7-dimethoxy-3,4-dihydroisoquinolinium iodide 
• 80053-50-5 6,7-methylenedioxy-3-chlorophthalide 
• 125239-01-2 Potassium; 8-oxo-6,8-dihydro-furo[3',4':3,4]benzo[1,2-d][1,3]dioxole-6-carboxylate 
• 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 
• 58343-48-9 5-formyl-benzo[1,3]dioxole-4-carboxylic acid 

Downstream Products

• 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.

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

3,4 Methylenedioxyphthalide α carboxylic acid: its use in the total synthesis of isoquinoline alkaloids

-