Angustoline

Base Information

• Chemical Name: Angustoline
• CAS No.: 40041-95-0
• Molecular Formula: C₂₀H₁₇N₃O₂
• Molecular Weight: 331.374
• DSSTox Substance ID: DTXSID90960503
• Nikkaji Number: J92.910G
• Wikidata: Q82941720
• Mol file: 40041-95-0.mol

Synonyms:angustoline

Chemical Property of Angustoline

Chemical Property:

• Boiling Point: 698.8°Cat760mmHg
• Flash Point: 376.4°C
• PSA: 70.91000
• Density: 1.46g/cm³
• LogP: 3.15420
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 331.132076794
• Heavy Atom Count: 25
• Complexity: 592

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=C2C=C3C4=C(CCN3C(=O)C2=CN=C1)C5=CC=CC=C5N4)O

Technology Process of Angustoline

There total 15 articles about Angustoline 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%

angustine (40041-96-1) → angustoline (40041-95-0,54713-51-8)

Guidance literature:

With manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; phenylsilane; oxygen; In ethanol; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2020.151757

Reference yield:

angustoline (40041-95-0,54713-51-8) → (+)-angustoline (40041-95-0) + (-)-angustoline

Guidance literature:

With chiral column Daicel Chiralpak IC; In methanol; dichloromethane; Resolution of racemate;

DOI:10.1016/j.tet.2014.09.026

Reference yield:

3,5-dibromo-4-methyl-pyridine (3430-23-7) → angustoline (40041-95-0,54713-51-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere

2.1: 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine / toluene / 2 h / 80 °C / Inert atmosphere

3.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine / ethanol / 4 h / 90 °C / Inert atmosphere

4.1: trichlorophosphate / 5 h / 80 °C / Inert atmosphere

4.2: 10 h / 60 °C / Inert atmosphere

5.1: manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; phenylsilane; oxygen / ethanol / 2 h / 20 °C

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; phenylsilane; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; oxygen; triethylamine; lithium hexamethyldisilazane; trichlorophosphate; In tetrahydrofuran; ethanol; toluene; 3.1: |Suzuki Coupling / 4.1: |Bischler-Napieralski Reaction;

DOI:10.1016/j.tetlet.2020.151757

upstream raw materials:

angustine

3,5-dibromo-4-methyl-pyridine

angustoline

Downstream raw materials:

C₃₀H₂₄F₃N₃O₄

C₃₀H₂₄F₃N₃O₄

Refernces

• 1、 Cao, Ruidi,Fu, Min,Liu, Xiao-Yu,Ou, Jingdan,Peng, Xin,Qin, Yong,Song, Hao. "Total synthesis of angustine and angustoline". . . Retrieved 2020/03/04.