Brefeldin C

Base Information

• Chemical Name: Brefeldin C
• CAS No.: 73899-78-2
• Molecular Formula: C₁₆H₂₄O₃
• Molecular Weight: 264.365
• Nikkaji Number: J91.910A
• Wikidata: Q104976313
• Mol file: 73899-78-2.mol

Synonyms:4H-Cyclopent[f]oxacyclotridecin-4-one,1,6,7,8,9,11a,12,13,14,14a-decahydro-1-hydroxy-6-methyl-,[1R-(1R*,2E,6S*,10E,11aS*,14aR*)]-; (+)-BFC; (+)-Brefeldin C; Brefeldin C

Chemical Property of Brefeldin C

Chemical Property:

• Vapor Pressure: 8.35E-10mmHg at 25°C
• Boiling Point: 445.4°C at 760 mmHg
• PKA: 13.06±0.40(Predicted)
• Flash Point: 185.9°C
• PSA: 46.53000
• Density: 1.032g/cm³
• LogP: 2.99160
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 264.17254462
• Heavy Atom Count: 19
• Complexity: 359

Purity/Quality:

99% ^*data from raw suppliers

BREFELDIN C 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCC=CC2CCCC2C(C=CC(=O)O1)O
• Isomeric SMILES: C[C@H]1CCC/C=C\[C@@H]2CCC[C@H]2[C@@H](/C=C\C(=O)O1)O

Technology Process of Brefeldin C

There total 81 articles about Brefeldin C 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: 100.0%

C25H44O3Si (1328893-44-2) → (+)-brefeldin C (73899-78-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;

DOI:10.1055/s-0030-1260762

Reference yield: 97.0%

(5E,13E)-(3aR,4R,9S,14aS)-4-(4-Methoxy-benzyloxy)-9-methyl-2,3,3a,9,10,11,12,14a-octahydro-1H,4H-8-oxa-cyclopentacyclotridecen-7-one (126761-02-2) → (+)-brefeldin C (73899-78-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water;

DOI:10.1016/S0040-4039(01)80524-4

Reference yield: 90.0%

4-dehydrobrefeldin C (115245-68-6) → (+)-brefeldin C (73899-78-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; at -78 ℃; for 0.75h;

DOI:10.1002/chem.201903392

upstream raw materials:

(5E,13E)-(3aR,4R,9S,14aS)-4-(4-Methoxy-benzyloxy)-9-methyl-2,3,3a,9,10,11,12,14a-octahydro-1H,4H-8-oxa-cyclopentacyclotridecen-7-one

4-dehydrobrefeldin C

(E)-3-Iodo-acrylic acid (E)-(S)-6-((1S,2R)-2-formyl-cyclopentyl)-1-methyl-hex-5-enyl ester

(1R,6S,11aS,14aR)-1-[(tert-butyldiphenylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

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