Aporeine

Base Information

• Chemical Name: Aporeine
• CAS No.: 2030-53-7
• Molecular Formula: C₁₈H₁₇NO₂
• Molecular Weight: 279.338
• UNII: 9C0X3XW6QA
• Nikkaji Number: J1.264.142G
• Wikidata: Q27272338
• ChEMBL ID: CHEMBL2365576
• Mol file: 2030-53-7.mol

Synonyms:aporeine;roemerine;roemerine hydrochloride, (R)-isomer;roemerine, (S)-isomer

Chemical Property of Aporeine

Chemical Property:

• Vapor Pressure: 2.13E-07mmHg at 25°C
• Melting Point: 102°
• Boiling Point: 424°Cat760mmHg
• PKA: 6.1(at 25℃)
• Flash Point: 162.4°C
• PSA: 21.70000
• Density: 1.269g/cm³
• LogP: 3.10530
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 279.125928785
• Heavy Atom Count: 21
• Complexity: 414

Purity/Quality:

>=95% ^*data from raw suppliers

Aporheine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C4=C2C1CC5=CC=CC=C54)OCO3
• Isomeric SMILES: CN1CCC2=CC3=C(C4=C2[C@@H]1CC5=CC=CC=C54)OCO3

Technology Process of Aporeine

There total 11 articles about Aporeine 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: 90.0%

(S)-methyl 7a,8-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]benzo[g]quinoline-7(6H)-carboxylate → (+)-roemerine (548-08-3,2030-53-7,15548-23-9)

Guidance literature:

(S)-methyl 7a,8-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]benzo[g]quinoline-7(6H)-carboxylate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 24h; Inert atmosphere;

With water; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/c7md00629b

Reference yield:

(+)-mecambroline (3466-56-6) → (+)-roemerine (548-08-3,2030-53-7,15548-23-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide

2: H₂ / Pd-C / acetic acid

With hydrogen; sodium hydride; palladium on activated charcoal; In acetic acid; N,N-dimethyl-formamide;

Reference yield:

(S)-7-methyl-11-(1-phenyl-1H-tetrazol-5-yloxy)-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline (71524-02-2) → (+)-roemerine (548-08-3,2030-53-7,15548-23-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid;

upstream raw materials:

(+/-)-roemerine

(S)-7-methyl-11-(1-phenyl-1H-tetrazol-5-yloxy)-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline

(-)-mecambrine

(+)-mecambroline

Downstream raw materials:

(+)-roemerine

roemerine

liriodenine

dehydroroemerine

Refernces

• 1、 Pfeifer,Thomas. "Alkaloids of the papaver family. 37. Papaver panosum Schwz. (P. spicatum Boiss. et Bal. var. spicatum), PL anomalum Fedde, P. pseudocanescens Pop., P. alboroseum Hulten". . p. 48 - 58. Retrieved 2007/10/04.