Antirhine

Base Information

• Chemical Name: Antirhine
• CAS No.: 16049-28-8
• Molecular Formula: C₁₉H₂₄N₂O
• Molecular Weight: 296.412
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40936319
• Wikidata: Q27105810
• Mol file: 16049-28-8.mol

Synonyms:Antirhine;16049-28-8;Anthirine;Rhazinine;(2R)-2-[(2S,12bS)-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]but-3-en-1-ol;C09033;CHEBI:2764;18,20-Seco-E-nor-15.beta.-yohimban-16.beta.-methanol, 17,18-didehydro-;DTXSID40936319;Indolo[2,3-a]quinolizine-2-ethanol, .beta.-ethenyl-1,2,3,4,6,7,12,12b-octahydro-, [2S-[2.alpha.(S*),12b.alpha.]]-;AKOS032948973;(2S,betaR)-beta-Vinyl-1,2,3,4,6,7,12,12bbeta-octahydroindolo[2,3-a]quinolizine-2-ethanol;Q27105810;2-(1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)but-3-en-1-ol;(2R)-2-[(2S,12BS)-1H,2H,3H,4H,6H,7H,12H,12BH-INDOLO[2,3-A]QUINOLIZIN-2-YL]BUT-3-EN-1-OL

Chemical Property of Antirhine

Chemical Property:

• Vapor Pressure: 2.4E-10mmHg at 25°C
• Boiling Point: 488.2°Cat760mmHg
• PKA: 14.72±0.10(Predicted)
• Flash Point: 249.1°C
• PSA: 39.26000
• Density: 1.2g/cm³
• LogP: 3.20950
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 296.188863393
• Heavy Atom Count: 22
• Complexity: 412

Purity/Quality:

> 95% ^*data from raw suppliers

Antirhine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC(CO)C1CCN2CCC3=C(C2C1)NC4=CC=CC=C34
• Isomeric SMILES: C=C[C@@H](CO)[C@H]1CCN2CCC3=C([C@@H]2C1)NC4=CC=CC=C34
• General Description: (2S,βR)-β-Vinyl-1,2,3,4,6,7,12,12bβ-octahydroindolo[2,3-a]quinolizine-2-ethanol, also known as (-)-antirhine or anthirine, is a chiral indoloquinolizine alkaloid derived from the enantiospecific synthesis of secologanin via glucoside hydrolysis and chemoselective reduction with baker's yeast, followed by a four-step transformation. Its structure features a β-vinyl group and an ethanol substituent on the octahydroindolo[2,3-a]quinolizine scaffold, with stereochemistry at the 2S and βR positions contributing to its biological and chemical properties.

Technology Process of Antirhine

There total 77 articles about Antirhine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

(2R,12bS)-2-((R)-1-Hydroxymethyl-allyl)-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-4-one → antirhine (16049-28-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; Heating;

DOI:10.1016/0040-4039(95)00543-L

Reference yield: 71.7%

(R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol (74447-18-0,137171-66-5) → (+/-)-antirhine (16049-28-8,34384-65-1,74497-05-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; -20 deg C -> room temperature;

DOI:10.1021/ja00532a061

Reference yield: 45.0%

(R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol (137171-66-5) → antirhine (16049-28-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/0040-4039(91)80018-2

upstream raw materials:

Anthirinal

(R)-4-(2-Nitro-phenylselanyl)-2-(2S,12bS)-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl-butan-1-ol

(1'S,2R,12bRS)-2-(1-hydroxymethyl-prop-2-enyl)-1,2,3,4,6,7,12,12b-octahydro-4-oxoindolo<2,3-a>-quinolizine

tryptamine

Downstream raw materials:

18,19-Dihydroantirhine

Dihydroantirhin