frangufoline

Base Information

• Chemical Name: frangufoline
• CAS No.: 19526-09-1
• Molecular Formula: C31H42 N4 O4
• Molecular Weight: 534.699
• ChEMBL ID: CHEMBL465983
• DSSTox Substance ID: DTXSID201317919
• Wikidata: Q105265566
• Mol file: 19526-09-1.mol

Synonyms:Benzenepropanamide,a-(dimethylamino)-N-[3-(1-methylethyl)-7-(2-methylpropyl)-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-10,12,14,15-tetraen-4-yl]-,[3S-[3R*,4R*(R*),7R*]]-; Frangufoline (8CI);2-Oxa-6,9-diazabicyclo[10.2.2]hexadecane, benzenepropanamide deriv.; DaechuineS1; NSC 226674; Sanjoinine A

Chemical Property of frangufoline

Chemical Property:

• Vapor Pressure: 3.77E-25mmHg at 25°C
• Boiling Point: 793°Cat760mmHg
• PKA: 12.68±0.70(Predicted)
• Flash Point: 433.4°C
• PSA: 99.77000
• Density: 1.15g/cm³
• LogP: 4.42760
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 534.32060583
• Heavy Atom Count: 39
• Complexity: 828

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1C(=O)NC=CC2=CC=C(C=C2)OC(C(C(=O)N1)NC(=O)C(CC3=CC=CC=C3)N(C)C)C(C)C
• Isomeric SMILES: CC(C)C[C@H]1C(=O)N/C=C\C2=CC=C(C=C2)O[C@H]([C@@H](C(=O)N1)NC(=O)[C@H](CC3=CC=CC=C3)N(C)C)C(C)C

Technology Process of frangufoline

There total 5 articles about frangufoline 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:

((Z)-(3S,4S,7S)-7-Isobutyl-3-isopropyl-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),10,12(16),13-tetraen-4-yl)-carbamic acid tert-butyl ester (136898-44-7) → sanjoinine A (19526-09-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 81 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂; tetrahydrofuran / 0.5 h / -40 °C

2: 87 percent / pyridine / 12 h

3: 76 percent / trifluoromethanesulfonic acid / 1,2-dichloro-ethane / 6 h

4: 81 percent / trifluoromethanesulfonic acid; N-iodosuccinimide / CH₂Cl₂; tetrahydrofuran; H₂O

5: 86 percent / cesium carbonate / CH₂Cl₂ / 2 h

6: 58 percent / BF₃*OEt₂ / CH₂Cl₂

7: 98 percent / NaOMe / methanol / 3.5 h

8: 90 percent / pyridine / CH₂Cl₂ / 2 h

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; caesium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; 1: Etherification / 2: Acetylation / 3: Ring cleavage / 4: Substitution / 5: Esterification / 6: Etherification / 7: deacylation / 8: Acylation;

DOI:10.1002/(sici)1099-0690(199910)1999:10<2623::aid-ejoc2623>3.0.co;2-k

Reference yield:

[3S,4S,7S,11S]-(11-hydroxy-7-isobutyl-3-isopropyl-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(15),12(16),13-trien-4-yl)-carbamic acid tert-butyl ester (136983-38-5) → sanjoinine A (19526-09-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / Dess-Martin periodination reagent / CH₂Cl₂

2: 96 percent / BH₃*THF / -78 - 20 °C

3: 1) 2-nitrophenylselenocyanate, Bu₃P, 2) H₂O₂, pyridine / 1) THF, 2) CH₂Cl₂

4: TMSOTf, 2,6-lutidine / CH₂Cl₂

5: 1) O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF₆, 2) K₂CO₃ / 1) DMF, 2) DMF

With pyridine; 2,6-dimethylpyridine; ortho-nitrophenyl selenocyanate; borane-THF; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; potassium carbonate; Dess-Martin periodane; HATU; In dichloromethane;

DOI:10.1016/S0040-4039(98)02278-3

Reference yield:

[3S,4S,7S,11R]-(11-hydroxy-7-isobutyl-3-isopropyl-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(15),12(16),13-trien-4-yl)-carbamic acid tert-butyl ester (136898-42-5) → sanjoinine A (19526-09-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) 2-nitrophenylselenocyanate, Bu₃P, 2) H₂O₂, pyridine / 1) THF, 2) CH₂Cl₂

2: TMSOTf, 2,6-lutidine / CH₂Cl₂

3: 1) O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium PF₆, 2) K₂CO₃ / 1) DMF, 2) DMF

With pyridine; 2,6-dimethylpyridine; ortho-nitrophenyl selenocyanate; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; potassium carbonate; HATU; In dichloromethane;

DOI:10.1016/S0040-4039(98)02278-3

upstream raw materials:

(2S)-2-(dimethylamino)-3-phenylpropanoic acid

(Z)-(3S,4S,7S)-4-Amino-7-isobutyl-3-isopropyl-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,10,12⁽¹⁶⁾,13-tetraene-5,8-dione

((Z)-(3S,4S,7S)-7-Isobutyl-3-isopropyl-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,10,12⁽¹⁶⁾,13-tetraen-4-yl)-carbamic acid tert-butyl ester

[3S,4S,7S,11S]-(11-hydroxy-7-isobutyl-3-isopropyl-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-4-yl)-carbamic acid tert-butyl ester

Downstream raw materials:

4-hydroxy-benzaldehyde

Sanjoinine-G₂