523-02-4

Basic information

• Product Name: (-)-Xylopinine
• Synonyms: [13aS,(-)]-5,8,13,13aα-Tetrahydro-2,3,10,11-tetramethoxy-6H-dibenzo[a,g]quinolizine;2,3,10,11-Tetramethoxy-13aα-Berbine;Govanine methyl ether;O-Methylgovanine
• CAS NO: 523-02-4
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.4275
• Mol File: 523-02-4.mol
• Article Data: 54

Chemical Properties

• Boiling Point: 476.2°C at 760 mmHg
• 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(523-02-4)
• EPA Substance Registry System: (-)-Xylopinine(523-02-4)

Safety Data

• Hazardous Substances Data: 523-02-4(Hazardous Substances Data)

Usage

Uses

(-?)?-?Xylopinine is a natural plant alkaloid with adrenoceptor (AR) α2 inhibiting activity.

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/t17-/m0/s1

Upstream product

• 78083-88-2 (6S,13aS)-2,3,10,11-Tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline-6-carbonitrile 
• 109717-71-7 (-)-protoberberine 
• 50-00-0 formaldehyd 
• 4747-98-2 S-(-)-Norlaudanosine 
• 79703-32-5 (S)-(-)-2,3,10,11-tetramethoxy-5,6,13,13a-tetrahydroisoquino[3,2-a]isoquinolin-8-one 
• 186581-53-3 diazomethane 
• 6957-27-3 3,4-dihydropapaverine 
• 863132-17-6 (3,4-dimethoxy-phenylethynyl)-trimethyl-silane 
• 863132-09-6 2-[2-(3,4-dimethoxy-phenylethynyl)-4,5-dimethoxy-phenyl]-ethylamine 
• 863132-19-8 N-{2-[2-(3,4-dimethoxy-phenylethynyl)-4,5-dimethoxy-phenyl]-ethyl}-2,2,2-trifluoro-acetamide 
• 91-16-7 1,2-dimethoxybenzene 
• 4302-52-7 4-ethynylveratrole 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 13230-71-2 N-[2-(3,4-dimethoxyphenyl)ethyl]-2,2,2-trifluoroacetamide 

Downstream Products

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

Relevant articles and documents

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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.

Total Synthesis of (-)-Canadine, (-)-Rotundine, (-)-Sinactine, and (-)-Xylopinine Using a Last-Step Enantioselective Ir-Catalyzed Hydrogenation

A concise asymmetric total synthesis of a group of tetrahydroprotoberberine alkaloids, (-)-canadine, (-)-rotundine, (-)-sinactine, and (-)-xylopinine, has been accomplished in three steps from the commercially available corresponding disubstituted phenylethylamine and disubstituted benzaldehyde. Our synthesis toward these four alkaloids took advantage of the following strategy: In the first step, we achieved an efficient and sustainable synthesis of secondary amine hydrochlorides via a fully continuous flow; in the second step, we developed a Pictet-Spengler reaction/Friedel-Crafts hydroxyalkylation/dehydration cascade for the construction of the dihydroprotoberberine core structure (ABCD-ring); and in the last step, Ir-catalyzed enantioselective hydrogenation was employed for the introduction of the desired stereochemistry at the C-14 position in the tetrahydroprotoberberine alkaloids. This work significantly expedites the asymmetric synthesis of the entire tetrahydroprotoberberine alkaloid family as well as a more diverse set of structurally related non-natural analogues.

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.