(-)-Caaverine

Base Information

• Chemical Name: (-)-Caaverine
• CAS No.: 6899-64-5
• Molecular Formula: C₁₇H₁₇NO₂
• Molecular Weight: 267.327
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00219034
• Nikkaji Number: J15.051G
• Wikidata: Q27105227
• Mol file: 6899-64-5.mol

Synonyms:(-)-Caaverine;2-Methoxynoraporphin-1-ol;NORAPORPHIN-1-OL, 2-METHOXY-;6899-64-5;1-Hydroxy-2-methoxynoraporphine;4H-Dibenzo(de,g)quinolin-1-ol, 5,6,6a,7-tetrahydro-2-methoxy-;(6aR)-2-methoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-1-ol;Caaverine;C09368;CHEBI:84;C18H18NO2;DTXSID00219034;C18-H18-N-O2;LS-97031;Q27105227

Chemical Property of (-)-Caaverine

Chemical Property:

• Vapor Pressure: 1.49E-09mmHg at 25°C
• Boiling Point: 472.5°Cat760mmHg
• Flash Point: 239.6°C
• PSA: 41.49000
• Density: 1.236g/cm³
• LogP: 3.13950
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 267.125928785
• Heavy Atom Count: 20
• Complexity: 361

Purity/Quality:

2-METHOXYNORAPORPHIN-1-OL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C2=C3C(CC4=CC=CC=C42)NCCC3=C1)O
• Isomeric SMILES: COC1=C(C2=C3[C@@H](CC4=CC=CC=C42)NCCC3=C1)O

Technology Process of (-)-Caaverine

There total 4 articles about (-)-Caaverine 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: 73.0%

(6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline (4846-19-9,20454-22-2,37659-74-8,54750-04-8) → caaverine (6899-64-5)

Guidance literature:

With sodium tetrahydroborate; dibenzyl diselenide; In N,N-dimethyl-formamide; regioselective reaction; Inert atmosphere; Reflux;

DOI:10.1007/s00044-013-0905-9

Reference yield:

R-(-)-nuciferine (475-83-2,5868-18-8,16654-38-9,37659-75-9) → caaverine (6899-64-5)

Guidance literature:

Multi-step reaction with 3 steps

1: dihydrogen peroxide / methanol / 24 h / 20 °C

2: ferrous(II) sulfate heptahydrate / methanol / 12 h / 0 - 20 °C

3: dibenzyl diselenide; sodium tetrahydroborate / N,N-dimethyl-formamide / Inert atmosphere; Reflux

With ferrous(II) sulfate heptahydrate; sodium tetrahydroborate; dibenzyl diselenide; dihydrogen peroxide; In methanol; N,N-dimethyl-formamide;

DOI:10.1007/s00044-013-0905-9

Reference yield:

(6S,6aR)-1,2-dimethoxy-6-methyl-6-oxo-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline (104385-30-0) → caaverine (6899-64-5)

Guidance literature:

Multi-step reaction with 2 steps

1: ferrous(II) sulfate heptahydrate / methanol / 12 h / 0 - 20 °C

2: dibenzyl diselenide; sodium tetrahydroborate / N,N-dimethyl-formamide / Inert atmosphere; Reflux

With ferrous(II) sulfate heptahydrate; sodium tetrahydroborate; dibenzyl diselenide; In methanol; N,N-dimethyl-formamide;

DOI:10.1007/s00044-013-0905-9

upstream raw materials:

R-(-)-nuciferine

(6S,6aR)-1,2-dimethoxy-6-methyl-6-oxo-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

(6aR)-1,2-dimethoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

Refernces