Pregnane-3,20-dione

Base Information

• Chemical Name: Pregnane-3,20-dione
• CAS No.: 7350-00-7
• Molecular Formula: C21H32O2
• Molecular Weight: 316.484
• DSSTox Substance ID: DTXSID80862209
• Nikkaji Number: J69.124K
• ChEMBL ID: CHEMBL3085573
• Mol file: 7350-00-7.mol

Synonyms:Pregnane-3,20-dione;Pregnan-3,20-dione;7350-00-7;20-BETA-DIHYDROPREGNANEDIONE;5xi-Pregnane-3,20-dione;SCHEMBL601902;5-alpha-Pregnan-3,20-dione;CHEMBL3085573;DTXSID80862209;LS-118537

Chemical Property of Pregnane-3,20-dione

Chemical Property:

• Vapor Pressure: 1.43E-07mmHg at 25°C
• Boiling Point: 429.2°Cat760mmHg
• Flash Point: 160.3°C
• PSA: 34.14000
• Density: 1.048g/cm³
• LogP: 4.80340
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 316.240230259
• Heavy Atom Count: 23
• Complexity: 538

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(=O)C4)C)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4[C@@]3(CCC(=O)C4)C)C

Technology Process of Pregnane-3,20-dione

There total 2 articles about Pregnane-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: 72.0%

Pregnenolone (145-13-1) → Progesterone (57-83-0) + pregnane-3,20-dione (7350-00-7)

Guidance literature:

aluminum oxide; copper; In toluene; at 60 ℃;

DOI:10.1021/jo00057a045

Reference yield:

Progesterone (57-83-0) → 16-dehydroprogesterone (1096-38-4) + 17-methyltestosterone (58-18-4) + Pregnenolone (145-13-1) + 21-Hydroxyprogesterone (64-85-7) + pregna-4,7-diene-3,20-dione (17398-60-6) + pregnane-3,6,20-trione (30802-24-5) + pregnane-3,20-dione (7350-00-7)

Guidance literature:

With Hortaea werneckii B-763 at all growth phases; In YNB growth medium; N,N-dimethyl-formamide; at 28 ℃; for 24h; Enzymatic reaction;

DOI:10.1016/j.steroids.2008.08.004

Reference yield:

5α-pregnan-3,20-dione (128-23-4,566-65-4,3986-74-1,4030-89-1,4030-90-4,4034-68-8,4155-84-4,4220-78-4,6570-76-9,7350-00-7,7755-34-2,14615-02-2,14957-73-4,36027-67-5,51154-64-4,51154-65-5,51154-66-6,51154-67-7,51154-68-8,51898-55-6,98301-13-4,102849-00-3) → 21-bromo-3β-(benzyloxymethyl)-3α-hydroxy-5α-pregnan-20-one

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium tert-butylate / dimethyl sulfoxide / 2 h / 65 °C / Industry scale

1.2: 2 h / 20 - 35 °C

2.1: benzyl alcohol / 16 h / 80 °C

2.2: 20 °C

3.1: bromine / hydrogen bromide / methanol; water / 1.5 h / 20 °C

With potassium tert-butylate; bromine; hydrogen bromide; In methanol; water; dimethyl sulfoxide; benzyl alcohol;

upstream raw materials:

Pregnenolone

Progesterone

Refernces

• 1、 Ravasio, Nicolette,Gargano, Michele,Rossi, Michele. "Selective Hydrogenations Promoted by Copper Catalysts. 2. Hydrogen-Transfer Reactions Leading to Stereoselective Hydrogenation of Δ5-3β-Sterols to 5β-Derivatives". . p. 1259 - 1261. Retrieved 2007/10/02.