6-Allyldihydronorisolysergic acid

Base Information

• Chemical Name: 6-Allyldihydronorisolysergic acid
• CAS No.: 86891-15-8
• Molecular Formula: C18H20N2O2
• Molecular Weight: 296.369
• DSSTox Substance ID: DTXSID501007177
• Mol file: 86891-15-8.mol

Synonyms:6-Allyldihydronorisolysergic acid;86891-15-8;(8-alpha)-6-(2-Propenyl)ergoline-8-carboxylic acid;Ergoline-8-carboxylic acid, 6-(2-propenyl)-, (8-alpha)-;(6aR,9S)-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylic acid;DTXSID501007177;LS-64391;6-(Prop-2-en-1-yl)ergoline-8-carboxylic acid

Chemical Property of 6-Allyldihydronorisolysergic acid

Chemical Property:

• Vapor Pressure: 4.45E-12mmHg at 25°C
• Boiling Point: 530.4°C at 760 mmHg
• PKA: 3.77±0.20(Predicted)
• Flash Point: 274.6°C
• PSA: 56.33000
• Density: 1.258g/cm³
• LogP: 2.70660
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 296.152477885
• Heavy Atom Count: 22
• Complexity: 466

Purity/Quality:

99% ^*data from raw suppliers

ERGOLINE-8-CARBOXYLIC ACID, 6-(2-PROPENYL)-, (8-ALPHA)- 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCN1CC(CC2C1CC3=CNC4=CC=CC2=C34)C(=O)O
• Isomeric SMILES: C=CCN1C[C@H](CC2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)O

Technology Process of 6-Allyldihydronorisolysergic acid

There total 4 articles about 6-Allyldihydronorisolysergic acid 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: 91.0%

(6aR,9S,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid methyl ester (86891-16-9) → (6aR,9S,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (86891-15-8)

Guidance literature:

With sodium hydroxide; In methanol; at 60 - 65 ℃; for 22h;

Reference yield:

(5R,8S,10R)-6-cyano-8-methoxycarbonylergoline (86891-18-1) → (6aR,9S,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (86891-15-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / hydrogen / Raney nickel / dimethylformamide / 130 h / 30 Torr / Ambient temperature

2: 91 percent / anhydrous potassium carbonate / dimethylformamide / 8 h / Ambient temperature

3: 91 percent / 0.2M NaOH / methanol / 22 h / 60 - 65 °C

With sodium hydroxide; hydrogen; potassium carbonate; nickel; In methanol; N,N-dimethyl-formamide;

Reference yield:

methyl (5R,8S,10R)-6-methyl-8-ergolinecarboxylate (5143-94-2) → (6aR,9S,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid (86891-15-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / CH₂Cl₂ / 5 h / 20 °C

2: 70 percent / hydrogen / Raney nickel / dimethylformamide / 130 h / 30 Torr / Ambient temperature

3: 91 percent / anhydrous potassium carbonate / dimethylformamide / 8 h / Ambient temperature

4: 91 percent / 0.2M NaOH / methanol / 22 h / 60 - 65 °C

With sodium hydroxide; hydrogen; potassium carbonate; nickel; In methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(6aR,9S,10aR)-7-Allyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid methyl ester

(5R,8S,10R)-6-cyano-8-methoxycarbonylergoline

(5R,8S,10R)-8-methoxycarbonylergoline

methyl (5R,8S,10R)-6-methyl-8-ergolinecarboxylate

Refernces