Pregna-4,6-diene-3,20-dione

Base Information

• Chemical Name: Pregna-4,6-diene-3,20-dione
• CAS No.: 1162-56-7
• Molecular Formula: C21H28 O2
• Molecular Weight: 312.452
• Hs Code.: 2937230000
• UNII: EF38VA583P
• Nikkaji Number: J28.121B
• Wikidata: Q27277145
• ChEMBL ID: CHEMBL4101936
• Mol file: 1162-56-7.mol

Synonyms:Pregna-4,6-diene-3,20-dione;1162-56-7;6-Dehydroprogesterone;Delta-6-progesterone;Dydrogesterone impurity B;delta6-Progesterone;4,6-Pregnadiene-3,20-dione;.delta.6-Progesterone;UNII-EF38VA583P;EF38VA583P;(8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one;6-Dehydropregesteron;Pregna-4,6-diene-3,20-dione (Delta6-Progesterone);SCHEMBL606817;CHEMBL4101936;BCP18804;MFCD00199858;AKOS015902046;AC-4529;AS-15619;CS-0155158;P2623;PROGESTERONE IMPURITY H [EP IMPURITY];DYDROGESTERONE IMPURITY B [EP IMPURITY];A803583;J-524052;Q27277145

Chemical Property of Pregna-4,6-diene-3,20-dione

Chemical Property:

• Vapor Pressure: 9.55E-09mmHg at 25°C
• Melting Point: 147-148 °C(Solv: hexane (110-54-3))
• Boiling Point: 462.8 °C at 760 mmHg
• Flash Point: 172.2 °C
• PSA: 34.14000
• Density: 1.1 g/cm³
• LogP: 4.49950
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 312.208930132
• Heavy Atom Count: 23
• Complexity: 628

Purity/Quality:

99.00% ^*data from raw suppliers

Pregna-4,6-diene-3,20-dione >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2C=CC4=CC(=O)CCC34C)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=CC4=CC(=O)CC[C@]34C)C
• Uses: 6-Dehydroprogesterone is an impurity found in progesterone. 6-Dehydroprogesterone is an impurity found in progesterone (P755900).

Technology Process of Pregna-4,6-diene-3,20-dione

There total 48 articles about Pregna-4,6-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: 86.3%

7-Dehydro-9β,10α-progesteron (16484-70-1) → dydrogesterone (601-33-2,1162-56-7,2640-38-2,3795-24-2,25093-47-4,152-62-5)

Guidance literature:

With hydrogen bromide; acetic acid; at 0 ℃; Reagent/catalyst;

Reference yield:

(9β,10α)-pregn-4-ene-3,20-dione (2755-10-4) → dydrogesterone (601-33-2,1162-56-7,2640-38-2,3795-24-2,25093-47-4,152-62-5)

Guidance literature:

With chloranil; In tert-butyl alcohol; at 20 - 85 ℃; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield:

Progesterone (57-83-0) → dydrogesterone (601-33-2,1162-56-7,2640-38-2,3795-24-2,25093-47-4,152-62-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 20 - 120 °C

2.1: rhodium(III) chloride hydrate; sodium periodate / tetrachloromethane; acetonitrile; water

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 20 - 80 °C

4.1: sodium tetrahydroborate; methanol / -55 °C

5.1: Rh/Al₂O₃; hydrogenchloride; hydrogen / water; ethanol / 20 °C

6.1: sodium hydroxide / tert-butyl alcohol / 0.5 h / 20 - 55 °C / Inert atmosphere

6.2: 1 h / 50 - 55 °C

7.1: chromium(VI) oxide; sulfuric acid / water; acetone / -10 - -5 °C

8.1: chloranil / tert-butyl alcohol / 20 - 85 °C / Inert atmosphere

With chromium(VI) oxide; hydrogenchloride; methanol; sodium tetrahydroborate; sodium periodate; rhodium(III) chloride hydrate; sulfuric acid; Rh/Al₂O₃; hydrogen; chloranil; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrachloromethane; ethanol; water; acetone; toluene; acetonitrile; tert-butyl alcohol;

upstream raw materials:

7-Dehydro-9β,10α-progesteron

Des-A-17α-Δ⁹-pregnen-5,20-dion

(9β,10α)-pregn-4-ene-3,20-dione

Progesterone

Downstream raw materials:

3-(pregn-4-ene-3,20-dione-7α-yl)thiopropanoic acid

9β,10α-Pregna-4,6,8(14)-trien-3,20-dion

6,7-dehydrocortisol 21-acetate

11α-hydroxy-5β-pregnane-3,20-dione

Refernces

• 1、 Turner. "". . p. 2568. Retrieved 1968.
• 2、 Shamsipur, Mojtaba,Pashabadi, Afshin,Taherpour, Avat (Arman),Bahrami, Kiumars,Sharghi, Hashem. "Manganese mediated oxidation of progesterone in alkaline medium: Mechanism study and quantitative determination". . p. 292 - 302. Retrieved 2017.
• 3、 Sondheimer et al.. "-". . p. 5932,5934. Retrieved 1953.
• 4、 -. "Method and compound for synthetizing reprogestin". Paragraph 0083-0088; 0089-0092; 0093-0096. . Retrieved 2021/09/15.
• 5、 -. "Production process capable of industrially synthesizing dydrogesterone". Paragraph 0090-0094. . Retrieved 2020/03/03.