1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, decahydro-4-(2-propenyl)-, (1S-(1alpha,4alpha,5alpha,11aalpha))-

Base Information

• Chemical Name: 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, decahydro-4-(2-propenyl)-, (1S-(1alpha,4alpha,5alpha,11aalpha))-
• CAS No.: 550-43-6
• Molecular Formula: C14H22 N2 O
• Molecular Weight: 234.341
• Wikidata: Q105292754
• Mol file: 550-43-6.mol

Synonyms:angustifoline

Chemical Property of 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, decahydro-4-(2-propenyl)-, (1S-(1alpha,4alpha,5alpha,11aalpha))-

Chemical Property:

• Vapor Pressure: 6.69E-06mmHg at 25°C
• Melting Point: 79-80 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 377.6°Cat760mmHg
• PKA: 10.07±0.40(Predicted)
• Flash Point: 182.1°C
• PSA: 32.34000
• Density: 1.1g/cm³
• LogP: 1.81820
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 234.173213330
• Heavy Atom Count: 17
• Complexity: 328

Purity/Quality:

HPLC≥95% ^*data from raw suppliers

Mixtureof(-)-AngustifolineandIsoangustifoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCC1C2CC(CN1)C3CCCC(=O)N3C2
• Isomeric SMILES: C=CC[C@H]1[C@@H]2C[C@H](CN1)[C@H]3CCCC(=O)N3C2
• Uses: (-)-Angustifoline is used in biological studies to determine the toxicity of dietary lupin alkaloids and its adverse effect.

Technology Process of 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, decahydro-4-(2-propenyl)-, (1S-(1alpha,4alpha,5alpha,11aalpha))-

There total 1 articles about 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, decahydro-4-(2-propenyl)-, (1S-(1alpha,4alpha,5alpha,11aalpha))- 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:

1,5-diaminopentane dihydrochloride (1476-39-7) → (+)-angustifoline (550-43-6,82189-28-4,150283-69-5) + (+)-lupanine (6R,7S,9S,11S) (486-87-3,486-88-4,550-90-3,2665-89-6,4356-43-8,26438-61-9,72074-77-2) + (+)-13α-hydroxylupanine (6870-60-6,14694-14-5,15358-48-2,27773-60-0,55820-85-4,55869-89-1)

Guidance literature:

With Lupinus polyphyllus plant; In water; for 360h; feeding experiment with 13C labelled cadaverine;

Reference yield:

(-)-Angustifoline (550-43-6) → (+)-lupanine (550-90-3)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 120 h

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1 h / Reflux

3: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C / 760.05 Torr

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium 10% on activated carbon; hydrogen; triethylamine; In methanol; dichloromethane;

DOI:10.1002/anie.201712852

upstream raw materials:

1,5-diaminopentane dihydrochloride

Downstream raw materials:

(+)-lupanine

Refernces