3alpha-Hydroxy-5alpha-pregna-9(11),16-diene-20-one

Base Information

• Chemical Name: 3alpha-Hydroxy-5alpha-pregna-9(11),16-diene-20-one
• CAS No.: 38393-04-3
• Molecular Formula: C21H30O2
• Molecular Weight: 314.468
• DSSTox Substance ID: DTXSID50959312
• Mol file: 38393-04-3.mol

Synonyms:3 alpha-hydroxy-5 alpha-pregna-9(11),16-diene-20-one;3-HPDO

Chemical Property of 3alpha-Hydroxy-5alpha-pregna-9(11),16-diene-20-one

Chemical Property:

• Vapor Pressure: 2.26E-10mmHg at 25°C
• Boiling Point: 459.5°Cat760mmHg
• Flash Point: 195.6°C
• PSA: 37.30000
• Density: 1.11g/cm³
• LogP: 4.43540
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 601

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CCC2C1(CC=C3C2CCC4C3(CCC(C4)O)C)C
• Isomeric SMILES: CC(=O)C1=CC[C@@H]2[C@@]1(CC=C3[C@H]2CC[C@@H]4[C@@]3(CC[C@H](C4)O)C)C

Technology Process of 3alpha-Hydroxy-5alpha-pregna-9(11),16-diene-20-one

There total 14 articles about 3alpha-Hydroxy-5alpha-pregna-9(11),16-diene-20-one 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: 80.0%

1-((3R,5S,8S,10S,13S,14S,16R,17S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,10,12,13,14,15,16-tetradecahydro-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-17-yl)-ethanone (96354-45-9) → 3α-Hydroxy-5α-pregna-9(11),16-dien-20-one (38393-04-3)

Guidance literature:

With lithium aluminium tetrahydride; titanium(III) chloride; In tetrahydrofuran; for 1.5h; Heating;

DOI:10.1016/S0039-128X(84)90120-X

Reference yield: 8.0%

1-[(5S,8S,10S,13S,14S)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,5,6,7,8,10,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-propan-1-one → 3β-hydroxy-5α-pregna-9(11),16-dien-20-one (5888-09-5,16300-80-4,38393-04-3,95044-19-2) + 3β-hydroxy-21-methyl-5α-pregna-9(11),16-diene-20-one (55652-83-0)

Guidance literature:

With water; acetic acid; Ambient temperature;

DOI:10.1039/P19810002306

Reference yield:

3-Iodo-benzoic acid (3R,5S,8R,9S,10S,13S,14S,16R,17S)-17-acetyl-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester (96354-43-7) → 3α-Hydroxy-5α-pregna-9(11),16-dien-20-one (38393-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / SO₂Cl₂, benzoyl peroxide / CCl₄ / 5 h / Heating

2: 80 percent / TiCl₃-LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

With lithium aluminium tetrahydride; sulfuryl dichloride; Perbenzoic acid; titanium(III) chloride; In tetrahydrofuran; tetrachloromethane;

DOI:10.1016/S0039-128X(84)90120-X

upstream raw materials:

3β-tetrahydropyranyloxy-5α-pregna-9(11),16-diene-20-one

1-((3R,5S,8S,10S,13S,14S,16R,17S)-3-Hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,10,12,13,14,15,16-tetradecahydro-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-17-yl)-ethanone

3-Iodo-benzoic acid (3R,5S,8R,9S,10S,13S,14S,16R,17S)-17-acetyl-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester

3-Iodo-benzoic acid (3R,5S,8S,9R,10S,13S,14S,16R,17S)-17-acetyl-9-chloro-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[16,17]cyclopenta[a]phenanthren-3-yl ester