6872-27-1

Basic information

• Product Name: XYLOPININE
• Synonyms: XYLOPININE;[13aR,(+)]-5,8,13,13aβ-Tetrahydro-2,3,10,11-tetramethoxy-6H-dibenzo[a,g]quinolizine;R-(+)-Xylopinine;β-Norcoralydine
• CAS NO: 6872-27-1
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.4275
• Mol File: 6872-27-1.mol
• Article Data: 45

Chemical Properties

• Boiling Point: 476.2°Cat760mmHg
• Flash Point: 136.3°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 3.12E-09mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: XYLOPININE(CAS DataBase Reference)
• NIST Chemistry Reference: XYLOPININE(6872-27-1)
• EPA Substance Registry System: XYLOPININE(6872-27-1)

Safety Data

• Hazardous Substances Data: 6872-27-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H25NO4/c1-23-18-8-13-5-6-22-12-15-10-20(25-3)19(24-2)9-14(15)7-17(22)16(13)11-21(18)26-4/h8-11,17H,5-7,12H2,1-4H3

Upstream product

• 31756-16-8 6,7-dimethoxy-2-veratryl-3,4-dihydro-isoquinolinium; chloride 
• 13074-31-2 Tetrahydropapaverine 
• 106544-61-0 2-(4,5-dimethoxy-2-((trimethylsilyl)methyl)benzyl)-6,7-dimethoxy-3,4-dihydroisoquinolinium perchlorate 
• 486-99-7 (S)-1-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 486-99-7 (6,7-dimethoxy-1,2,3,4-tetrahydro-1-isoquinolyl)methanol 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 289507-36-4 2-(2-bromo-4,5-dimethoxyphenyl)ethyl alcohol 
• 69327-12-4 1-bromo-2-(2-bromoethyl)-4,5-dimethoxybenzene 
• 50-00-0 formaldehyd 
• 109-87-5 Dimethoxymethane 
• 101481-11-2 Phosphoric acid diethyl ester 2,3,10,11-tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinolin-12-yl ester 
• 332951-52-7 7,14-dehydroxylopinine 
• 75938-11-3 2-(3',4'-Dimethoxy-β-phenethyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-3-isoquinolone 
• 55276-83-0 5,6-dihydro-2,3,10,11-tetramethoxy-8H-dibenzoquinolizine 

Downstream Products

• 120021-26-3 3-(2-vinyl-4,5-dimethoxyphenyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 6899-65-6 (+/-)-O-methylcorytenchirine 
• 19716-66-6 pseudopalmatine 
• 52194-51-1 (+/-)-Xylopinin-trans-methiodid 
• 57129-74-5 (+/-)-N-methylxylopinine iodide 

Relevant articles and documents

One-pot tandem route to fused indolizidines and quinolizidines: Application in the synthesis of alkaloids and bioactive compounds

Fused indolizidines and quinolizidines are important skeletons in a variety of natural products and pharmacologically important compounds. A one-pot tandem route from amide to fused indolizidines and quinolizidines is disclosed. This method is conducted in mild conditions and shows well tolerance of functional groups. It is also easy to be scaled up to gram scale and can be applied smoothly to the total synthesis of alkaloids such as (±)-crispine A, (±)-xylopinine, (±)-desbromoarborescidine A, (±)-harmicine and other bioactive substances.

Stereoselective construction of a berberine C-8 benzyl group for the synthesis of javaberine derivatives

Diastereoselective synthesis of 8-benzyltetrahydroprotoberberines was examined. Although Stevens rearrangement of N-benzylxylopinine resulted in poor yield and diastereoselectivity, benzylation of tetracyclic iminium successfully gave H8-H14 trans-benzyltetrahydroprotoberberines with high stereoselectivity.

Green synthesis technology of rotundine sulfate

The invention provides a green synthesis technology of rotundine sulfate. The green synthesis technology comprises the following steps: firstly, taking pyrocatechol as a starting reactant, and carrying out esterification, acylation and nitration; then carrying out deoxygenation reduction to obtain 3,4-dimethoxyphenethylamine; then carrying out condensation on the obtained 3,4-dimethoxyphenethylamine and 2,3-dimethoxy benzaldehyde and reducing to obtain (3,4-dimethoxy)phenethyl(2,3-dimethoxy)benzylamine; finally, carrying out cyclization, reduction and sulfation on the obtained (3,4-dimethoxy)phenethyl(2,3-dimethoxy)benzylamine, so as to obtain finished-product rotundine sulfate. The invention develops a full-synthesis technology taking the pyrocatechol as a raw material, and provides an environment-friendly, low-cost and high-yield green synthesis technology for synthesizing the rotundine sulfate.