17-Hydroxy-1a,2a-methylenepregna-4,6-diene-3,20-dione acetate

Base Information

• Chemical Name: 17-Hydroxy-1a,2a-methylenepregna-4,6-diene-3,20-dione acetate
• CAS No.: 2701-50-0
• Molecular Formula: C24H30O4
• Molecular Weight: 382.5
• European Community (EC) Number: 427-820-5
• UNII: 689QR3QTC2
• DSSTox Substance ID: DTXSID201129275
• Mol file: 2701-50-0.mol

Synonyms:2701-50-0;17-Hydroxy-1a,2a-methylenepregna-4,6-diene-3,20-dione acetate;6-Deschloro Cyproterone Acetate;(1beta,2beta)-17-(Acetyloxy)-1,2-dihydro-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione;ARUYPSAYKHCXNE-UQNNAPNASA-N;6-Deschloro-cyproterone acetate;689QR3QTC2;SCHEMBL9168274;DTXSID201129275;(2aR,3aS,3bS,3cS,5aS,6R,8aS,8bR)-6-acetyl-3b,5a-Dimethyl-2-oxo-2,2a,3,3a,3b,3c,4,5,5a,6,7,8,8a,8b-tetradecahydrocyclopenta[a]cyclopropa[g]phenanthren-6-yl acetate;BCP08488;AKOS025285998;CYPROTERONE ACETATE IMPURITY A [EP IMPURITY];17alpha-acetoxy-1alpha,2alpha-methylene-4,6-pregnadiene-3,20-dione;17-Hydroxy-1alpha,2alpha-methylenepregna-4,6-diene-3,20-dione acetate;Pregna-4,6-diene-3,20-dione, 17-hydroxy-1|A,2|A-methylene-, acetate;3,20-dioxo-1beta,2beta-dihydro-3'H-cyclopropa[1,2]pregna-1,4,6-trien-17-yl acetate;3'H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-1,2-dihydro-, (1beta,2beta)-

Chemical Property of 17-Hydroxy-1a,2a-methylenepregna-4,6-diene-3,20-dione acetate

Chemical Property:

• Melting Point: 280-281 °C
• Refractive Index: 1.576
• Boiling Point: 518.4 °C at 760 mmHg
• Flash Point: 224.7 °C
• PSA: 60.44000
• Density: 1.21 g/cm³
• LogP: 4.04110
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 382.21440943
• Heavy Atom Count: 28
• Complexity: 853

Purity/Quality:

99.00% ^*data from raw suppliers

6-DeschloroCyproteroneAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CCC2C1(CCC3C2C=CC4=CC(=O)C5CC5C34C)C)OC(=O)C
• Isomeric SMILES: CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=CC4=CC(=O)[C@@H]5C[C@@H]5[C@]34C)C)OC(=O)C
• Uses: An impurity of Cyproterone acetate 6-Deschloro Cyproterone Acetate (Cyproterone Acetate EP Impurity A) is an impurity of Cyproterone acetate (C989100).

Technology Process of 17-Hydroxy-1a,2a-methylenepregna-4,6-diene-3,20-dione acetate

There total 6 articles about 17-Hydroxy-1a,2a-methylenepregna-4,6-diene-3,20-dione acetate 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:

17α-hydroxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione (2098-65-9) + acetic anhydride (108-24-7) → 1,2α-methylene-Δ4,6-pregnadiene-17α-ol-3,20-dione-17-acetate (2701-50-0)

Guidance literature:

In chloroform; at 58 ℃; Temperature;

Reference yield:

1,4,6-triene-3,20-dione-17α-hydroxyprogesterone (66212-25-7) → 1,2α-methylene-Δ4,6-pregnadiene-17α-ol-3,20-dione-17-acetate (2701-50-0)

Guidance literature:

Multi-step reaction with 4 steps

1: orthoformic acid triethyl ester / dichloromethane / 5 h / 30 °C

2: N,N-dimethyl-formamide / 3 h / 42 °C

3: sulfuric acid / N,N-dimethyl-formamide / 2 h / pH 2

4: chloroform / 58 °C

With sulfuric acid; orthoformic acid triethyl ester; In dichloromethane; chloroform; N,N-dimethyl-formamide;

Reference yield:

C23H30O4 → 1,2α-methylene-Δ4,6-pregnadiene-17α-ol-3,20-dione-17-acetate (2701-50-0)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-dimethyl-formamide / 3 h / 42 °C

2: sulfuric acid / N,N-dimethyl-formamide / 2 h / pH 2

3: chloroform / 58 °C

With sulfuric acid; In chloroform; N,N-dimethyl-formamide;

upstream raw materials:

17α-hydroxy-1α,2α-methylene-4,6-pregnadiene-3,20-dione

acetic anhydride

1,4,6-triene-3,20-dione-17α-hydroxyprogesterone

Downstream raw materials:

1,2α-methylene-6,7α-oxido-Δ4-pregnen-17α-ol-3,20-dione-17-acetate

6-chloro-1α-chloromethyl-Δ4,6-pregnadien-17α-ol-3,20-dione-17-acetate

cyproterone acetate