16,17-Didehydro-11-oxoprogesterone

Base Information

• Chemical Name: 16,17-Didehydro-11-oxoprogesterone
• CAS No.: 1882-86-6
• Molecular Formula: C₂₁H₂₆O₃
• Molecular Weight: 326.436
• NSC Number: 29841
• UNII: 382CL6DTZL
• DSSTox Substance ID: DTXSID30172168
• Nikkaji Number: J863.028C
• Wikidata: Q27148787
• Mol file: 1882-86-6.mol

Synonyms:16,17-Didehydro-11-oxoprogesterone;1882-86-6;Pregna-4,16-diene-3,11,20-trione;UNII-382CL6DTZL;382CL6DTZL;NSC 29841;NSC-29841;SCHEMBL10728432;CHEBI:79664;DTXSID30172168;NSC29841;4,16-pregnadien-3,11,20-trione;Q27148787

Chemical Property of 16,17-Didehydro-11-oxoprogesterone

Chemical Property:

• Vapor Pressure: 2.66E-10mmHg at 25°C
• Boiling Point: 504.4°Cat760mmHg
• Flash Point: 217.4°C
• Density: 1.17g/cm³
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 326.18819469
• Heavy Atom Count: 24
• Complexity: 713

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CCC2C1(CC(=O)C3C2CCC4=CC(=O)CCC34C)C
• Isomeric SMILES: CC(=O)C1=CC[C@@H]2[C@@]1(CC(=O)[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C

Technology Process of 16,17-Didehydro-11-oxoprogesterone

There total 35 articles about 16,17-Didehydro-11-oxoprogesterone 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: 75.0%

(2R,3S,3aS,5aR,6R,9aS,9bS)-3-Acetyl-2-(tert-butyl-dimethyl-silanyloxy)-3a,6-dimethyl-6-(3-oxo-butyl)-decahydro-cyclopenta[a]naphthalene-5,7-dione (104621-28-5,122314-91-4) → 11-Keto-16-dehydroprogesterone (1882-86-6,110785-85-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 230 ℃; for 3h;

DOI:10.1021/ja00198a042

Reference yield: 75.0%

(2R,3S,3aS,5aR,6R,9aS,9bS)-3-Acetyl-2-(tert-butyl-dimethyl-silanyloxy)-3a,6-dimethyl-6-(3-oxo-butyl)-decahydro-cyclopenta[a]naphthalene-5,7-dione (104621-28-5,122314-91-4) → (8S,9R,10R,13S,14S)-17-Acetyl-10,13-dimethyl-1,6,7,8,9,10,12,13,14,15-decahydro-2H-cyclopenta[a]phenanthrene-3,11-dione (1882-86-6,110785-85-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 230 ℃; for 3h;

DOI:10.1021/jo00372a052

Reference yield: 50.0%

methanol (67-56-1) + (2R,3S,3aS,5aR,6R,9aS,9bS)-3-Acetyl-2-(tert-butyl-dimethyl-silanyloxy)-3a,6-dimethyl-6-(3-oxo-butyl)-decahydro-cyclopenta[a]naphthalene-5,7-dione (104621-28-5,122314-91-4) → 11-Keto-16-dehydroprogesterone (1882-86-6,110785-85-8) + (8R,9R,10S,13R,14R,16S,17R)-17-Acetyl-16-methoxy-10,13-dimethyl-1,6,7,8,9,10,12,13,14,15,16,17-dodecahydro-2H-cyclopenta[a]phenanthrene-3,11-dione (122314-93-6)

Guidance literature:

With potassium hydroxide;

DOI:10.1021/ja00198a042

upstream raw materials:

11α-hydroxy-4,16-dien-pregnan-3,20-dione

17-bromo-pregn-4-ene-3,11,20-trione

sodium acetate

acetic acid

Downstream raw materials:

(+/-)-cortisone

(+/-)-adrenosterone

(+/-)-Cortisone

(+/-)-adrenosterone