475-75-2

Basic information

• Product Name: liriodenine
• Synonyms: liriodenine;8H-Benzo[G]-1,3-benzodioxolo[6,5,4-de]quinolin-8-one;Micheline b;Noraporphin-7-one, 4,5,6,6A-tetradehydro-1,2-(methylenedioxy)-;Nsc93681;Oxoushinsunin;Oxoushinsunine;Spermatheridin
• CAS NO: 475-75-2
• Molecular Formula: C17H9NO3
• Molecular Weight: 275.262
• Mol File: 475-75-2.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 531°Cat760mmHg
• Flash Point: 275°C
• Appearance: /
• Density: 1.501g/cm³
• Vapor Pressure: 2.33E-11mmHg at 25°C
• Refractive Index: 1.767
• CAS DataBase Reference: liriodenine(CAS DataBase Reference)
• NIST Chemistry Reference: liriodenine(475-75-2)
• EPA Substance Registry System: liriodenine(475-75-2)

Safety Data

• Hazardous Substances Data: 475-75-2(Hazardous Substances Data)

Usage

Description

Isolated from the heartwood extract of Liriodendron tulip/era, this base may be purified by crystallization from CHCI3. It contains one methylenedioxy group and a keto group, forming a crystalline oxime, m.p. 271°C. The structure has been confirmed by synthesis, the synthetic alkaloid having a higher melting point of 287°C.

Uses

Liriodenine is an isoquinoline alkaloid found in extracts of medicinal Asian vegetation such as Michelia alba and Liriodendron chinense.

Definition

ChEBI: An oxoaporphine alkaloid that is 4,5,6,6a-tetradehydronoraporphin-7-one substituted by a methylenedioxy group across positions 1 and 2. It is isolated from Annona glabra and has been shown to exhibit antimicrobial and cytotoxic activities.

References

Buchanan, Dickey.,J. Org. Chern., 25, 1389 (1960) Taylor., Tetrahedron, 14,42 (1961)

InChI:InChI=1/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2

Upstream product

• 269-44-3 papraline 
• 54879-81-1 (2H-1,3-benzodioxol-5-ylmethyl)(2,2-dimethoxyethyl)amine 
• 39964-90-4 N-(2,2-dimethoxyethyl)-N-<(3,4-methylenedioxyphenyl)methyl>-p-toluenesulfonamide 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 
• 934355-59-6 tert-butyl 5-(2-bromobenzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-6(5H)-carboxylate 
• 87201-31-8 1-(2'-bromobenzyl)-3,4-dihydro-6,7-methylenedioxyisoquinoline 
• 6006-82-2 3,4-methylenedioxyphenethyl alcohol 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 73903-40-9 5-(2-nitro-benzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 1485-00-3 5-((E)-2-nitroethenyl)-1,3-benzodioxole 
• 120-57-0 piperonal 
• 73903-39-6 N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-2-(2-nitrophenyl)acetamide 
• 24188-76-9 [1,3]dioxolo[4,5-g]isoquinolin-5(6H)-one 
• 1432725-49-9 1-iodo-6,7-(methylenedioxy)isoquinoline 

Relevant articles and documents

Two antimicrobial alkaloids from heartwood of Liriodendron tulipifera L.

Alcoholic extracts of the heartwood of Liriodendron tulipifera have demonstrated antimicrobial activity against Staphylococcus aureus, Myobacterium smegmatis, Candida albicans, and Aspergillus niger. The antimicrobial activity was associated only with the alkaloidal fraction. Separation of the active alkaloidal fraction by chromatography led to the isolation and identification of dehydroglaucine and liriodenine as the active components. Several other alkaloidal derivatives were prepared and tested. In addition to the active alkaloids, michelalbine was also identified in the tertiary nonphenolic base fraction along with the lignan, lirioresinol B dimethyl ether, and two N acetylnoraporphine alkaloids from the nonbasic fraction.

Development of Pd(OAc)2-catalyzed tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds: Concise synthesis of 1-aroylisoquinoline, oxoaporphine, and 8-oxyprotoberberine alkaloids

A catalytic tandem oxidation of C[sbnd]N, C[sbnd]C, and C(sp3)–H bonds is developed. This tandem oxidation is applied to two-step total syntheses of papaveraldine and pulcheotine A. Additionally, the total synthesis of liriodenine is achieved in six steps from homopiperonyl alcohol and 2-bromophenylacetonitrile by applying this catalytic tandem oxidation. Moreover, the direct conversion of xylopinine to 8-oxypseudopalmatine in a 76% yield demonstrates the versatility of this catalytic reaction.

Novel total syntheses of oxoaporphine alkaloids enabled by mild Cu-catalyzed tandem oxidation/aromatization of 1-Bn-DHIQs

Novel total syntheses of oxoaporphine alkaloids such as liriodenine, dicentrinone, cassameridine, lysicamine, oxoglaucine and O-methylmoschatoline were developed. The key step of these total syntheses is Cu-catalyzed conversion of 1-benzyl-3,4-dihydro-isoquinolines (1-Bn-DHIQs) to 1-benzoyl-isoquinolines (1-Bz-IQs) via tandem oxidation/aromatization. This novel Cu-catalyzed conversion has been studied in detail, and was successfully used for constructing the 1-Bz-IQ core.

THE SYNTHESIS OF OXOAPORPHINES AND PHENANTHRENEDIONES FROM 7-HYDROXYDEHYDRONORAPORPHINES

Oxidation of 7-hydroxydehydronoraporphines with air over platinum or palladium yields oxoaporphines in high yield.When the nitrogen is acylated, oxidation with air in the presence of copper ions causes an oxidative ring fragmentation to form phenanthrenediones, also in high yield.