Methyl 6alpha-bromo-7-oxo-O-methylpodocarpate

Base Information

• Chemical Name: Methyl 6alpha-bromo-7-oxo-O-methylpodocarpate
• CAS No.: 1045-54-1
• Molecular Formula: C₁₉H₂₃BrO₄
• Molecular Weight: 395.293
• DSSTox Substance ID: DTXSID20909006
• Mol file: 1045-54-1.mol

Synonyms:Methyl 6alpha-bromo-7-oxo-O-methylpodocarpate;1045-54-1;Methyl 6alpha-bromo-12-methoxy-7-oxopodocarpa-8,11,13-trien-16-oate;Podocarpa-8,11,13-trien-16-oic acid, 6alpha-bromo-12-methoxy-7-oxo-, methyl ester;C19H23BrO4;SCHEMBL19786283;C19-H23-Br-O4;DTXSID20909006;Methyl 6-bromo-12-methoxy-7-oxopodocarpa-8,11,13-trien-15-oate;Podocarpa-8,11,13-trien-16-oic acid, 6.alpha.-bromo-12-methoxy-7-oxo-, methyl ester

Chemical Property of Methyl 6alpha-bromo-7-oxo-O-methylpodocarpate

Chemical Property:

• Vapor Pressure: 2.52E-09mmHg at 25°C
• Boiling Point: 478.7°C at 760 mmHg
• Flash Point: 243.3°C
• Density: 1.345g/cm³
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 394.07797
• Heavy Atom Count: 24
• Complexity: 536

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(C1C(C(=O)C3=C2C=C(C=C3)OC)Br)(C)C(=O)OC
• Isomeric SMILES: C[C@]12CCC[C@](C1[C@H](C(=O)C3=C2C=C(C=C3)OC)Br)(C)C(=O)OC

Technology Process of Methyl 6alpha-bromo-7-oxo-O-methylpodocarpate

There total 5 articles about Methyl 6alpha-bromo-7-oxo-O-methylpodocarpate 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: 81.0%

methyl 12-methoxy-7-oxopodocarpa-8,11,13-trien-19-oate (901-36-0,1245641-48-8) → 6α-Brom-7-oxo-O-methylpodocarpsaeure-methylester (1045-54-1)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; for 96h; Ambient temperature; Irradiation;

DOI:10.1002/jps.2600730528

Reference yield: 3.0%

→ 6α-Brom-7-oxo-O-methylpodocarpsaeure-methylester (1045-54-1) + methyl 6α,13-dibromo-12-methoxy-7-oxopodocarpa-8,11,13-trien-19-oate (143701-53-5) + methyl 6α,14-dibromo-12-methoxy-7-oxo-podocarpa-8,11,13-trien-19-oate (143701-52-4)

Guidance literature:

With bromine; In tetrachloromethane; for 0.75h; Ambient temperature;

DOI:10.1016/0022-328X(92)80117-G

Reference yield:

methyl O-methylpodocarpate (1231-74-9) → 6α-Brom-7-oxo-O-methylpodocarpsaeure-methylester (1045-54-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / chromium trioxide / acetic acid; H₂O / Ambient temperature

2: 81 percent / N-bromosuccinimide / CCl₄ / 96 h / Ambient temperature; Irradiation

With chromium(VI) oxide; N-Bromosuccinimide; In tetrachloromethane; water; acetic acid;

DOI:10.1002/jps.2600730528

upstream raw materials:

methyl 12-methoxy-7-oxopodocarpa-8,11,13-trien-19-oate

methyl O-methylpodocarpate

Downstream raw materials:

(1S,4aR)-6-Methoxy-1,4a-dimethyl-2,3,4,4a-tetrahydro-1H-phenanthren-9-one

methyl O-methyl-Δ^5,6-7-ketopodocarpate

methyl 12-methoxy-7-oxopodocarpa-8,11,13-trien-19-oate