Pregna-4,9(11)-diene-3,20-dione

Base Information

• Chemical Name: Pregna-4,9(11)-diene-3,20-dione
• CAS No.: 17652-16-3
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.452
• UNII: 25T39R854K
• Nikkaji Number: J2.746.252I
• Wikidata: Q27102054
• Metabolomics Workbench ID: 34824
• Mol file: 17652-16-3.mol

Synonyms:Pregna-4,9(11)-diene-3,20-dione;9-Dehydro-Progesterone;25T39R854K;Progesterone impurity K [EP];UNII-25T39R854K;17652-16-3;9,11-Dehydroprogesterone;SCHEMBL4815027;CHEBI:16744;LMST01031018;Pregna-4,9(11)-diene-3,20-dione #;PROGESTERONE IMPURITY K [EP IMPURITY];Q27102054;(8S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one

Chemical Property of Pregna-4,9(11)-diene-3,20-dione

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 312.208930132
• Heavy Atom Count: 23
• Complexity: 640

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

9-DEHYDRO-PROGESTERONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CC=C3C2CCC4=CC(=O)CCC43C)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC=C3[C@H]2CCC4=CC(=O)CC[C@@]43C)C

Technology Process of Pregna-4,9(11)-diene-3,20-dione

There total 36 articles about Pregna-4,9(11)-diene-3,20-dione 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: 46.0%

methylmagnesium bromide (75-16-1) + C24H34O5 (101387-16-0,108355-25-5) → Δ9-progesterone (4085-88-5,17652-16-3,24742-95-8,108393-80-2)

Guidance literature:

In diethyl ether; at 0 ℃; for 0.0833333h;

Reference yield:

9α-hydroxypregn-4-ene-3,20-dione (15981-54-1) → pregna-4,9(11)-diene-3,20-dione (17652-16-3)

Guidance literature:

In sulfuric acid; water; ethyl acetate;

Reference yield:

(8S,9S,10R,11S,13S,14S,17S)-17-Acetyl-11-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (600-57-7,22847-91-2) → pregna-4,9(11)-diene-3,20-dione (17652-16-3)

Guidance literature:

With hydrogenchloride; acetic acid;

DOI:10.1021/ja01637a061 DOI:10.1002/hlca.19410240151

upstream raw materials:

(8S,9S,10R,11S,13S,14S,17S)-17-Acetyl-11-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

11α-hydroxyprogesterone toluene-p-sulphonate

11-alpha-hydroxyprogesterone

9α-hydroxypregn-4-ene-3,20-dione

Downstream raw materials:

dihydroprogesterone

Refernces

• 1、 -. "17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one". . . Retrieved 2008/06/13.
• 2、 Nemoto, Hideo,Nagai, Mitsuo,Fukumoto, Keiichiro,Kametani, Tetsuji. "A Stereoselective Total Synthesis of 11-Oxoprogesterone, a Precursor to the Corticosteroids, via an Intramolecular Cycloaddition Reaction". . p. 1621 - 1626. Retrieved 2007/10/02.