Angustine

Base Information

• Chemical Name: Angustine
• CAS No.: 40041-96-1
• Molecular Formula: C20H15N3O
• Molecular Weight: 313.3526
• DSSTox Substance ID: DTXSID20193105
• Nikkaji Number: J19.319D
• Wikidata: Q27105783
• Metabolomics Workbench ID: 69063
• Mol file: 40041-96-1.mol

Synonyms:angustine

Chemical Property of Angustine

Chemical Property:

• Boiling Point: 648.2°Cat760mmHg
• Flash Point: 345.8°C
• PSA: 50.68000
• Density: 1.4g/cm³
• LogP: 3.74390
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 313.121512110
• Heavy Atom Count: 24
• Complexity: 585

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1=CN=CC2=C1C=C3C4=C(CCN3C2=O)C5=CC=CC=C5N4
• Description: A synthesis of angustine has recently been reported. Ethyl oxalate is condensed with 4-methyl-5-vinylinicotinonitrile followed by condensation of the lactone thus produced with tryptamine. Hydrolysis and then cyclization of the product yields angustine.

Technology Process of Angustine

There total 17 articles about Angustine 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: 95.0%

tri-n-butyl(vinyl)tin (7486-35-3) + 20-bromonauclefine (62298-30-0) → angustine (40041-96-1)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; toluene; at 100 ℃;

DOI:10.1039/c39950001675

Reference yield: 94.0%

13b,14-dihydroangustine (97168-60-0,116965-55-0,142234-96-6) → angustine (40041-96-1)

Guidance literature:

With iodine; In methanol; for 12h; Heating;

DOI:10.1016/S0040-4020(01)80085-5

Reference yield:

C19H18BrN3O + chloroacetic acid ethyl ester (105-39-5) → angustine (40041-96-1)

Guidance literature:

C₁₉H₁₈BrN₃O; With trichlorophosphate; at 80 ℃; for 5h; Inert atmosphere;

chloroacetic acid ethyl ester; With dicobalt octacarbonyl; potassium carbonate; In methanol; at 60 ℃; for 10h; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.151757

upstream raw materials:

13b,14-dihydroangustine

tri-n-butyl(vinyl)tin

20-bromonauclefine

5-bromo-3-pyridinecarboxylic acid

Downstream raw materials:

angustoline

(+)-angustoline

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.
• 2、 Lavilla, Rodolfo,Gullón, Francisco,Bosch, Joan. "A unified synthetic strategy for the indolopyridine alkaloid group". . p. 373 - 378. Retrieved 2007/10/03.