[(10R,13S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate

Base Information

• Chemical Name: [(10R,13S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
• CAS No.: 302-22-7
• Molecular Formula: C23H29ClO4
• Molecular Weight: 404.934
• Hs Code.: 29372390
• NSC Number: 758967
• ChEMBL ID: CHEMBL3039366
• Mol file: 302-22-7.mol

Synonyms:[(10R,13S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate;Spectrum3_001992;BSPBio_003592;SPECTRUM1505327;SCHEMBL4948575;CHEMBL3039366;KBio3_003029;NPD5386;BDBM233043;HMS1922D14;HMS2093B19;HMS3374I03;Pharmakon1600-01505327;CCG-38997;NSC758967;NSC-758967;NCGC00177976-01;SBI-0206750.P001;AB01563060_01;SR-05000002004;SR-05000002004-1;BRD-A01593789-001-01-5;BRD-A01593789-001-02-3;6-Chloro-3,20-dioxopregna-4,6-diene-17alpha-yl acetate (9)

Chemical Property of [(10R,13S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 1.28E-10mmHg at 25°C
• Melting Point: 212 °C
• Refractive Index: 1.562
• Boiling Point: 512.5 °C at 760 mmHg
• Flash Point: 172.5 °C
• PSA: 60.44000
• Density: 1.23 g/cm³
• LogP: 4.75170
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 404.1754371
• Heavy Atom Count: 28
• Complexity: 827

Purity/Quality:

99% ^*data from raw suppliers

Chlormadinone acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 60-61-40-48
• Safety Statements: 53-22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(=O)CCC34C)Cl)C)OC(=O)C
• Isomeric SMILES: CC(=O)[C@]1(CCC2[C@@]1(CCC3C2C=C(C4=CC(=O)CC[C@]34C)Cl)C)OC(=O)C
• Description: Chlormadinone acetate is a synthetic progestin. It binds to progesterone, androgen, and glucocorticoid receptors in vitro (Kis = 2.5, 3.8, and 16 nM, respectively, for the human receptors). Chlormadinone acetate increases the number of endometrial glands and uterine weight in β-estradiol-primed rabbits when administered at a dose of 45 μg/kg per day for five days. Chlormadinone acetate reduces testosterone-induced increases in the seminal vesicle weight of castrated male rats when administered at doses of 4.6 and 21.5 mg/kg per day for eight days.
• Uses: Orally active progesteron with antiandrogenic activity; has been used in combinations as an oral contraceptive. Progestogen; antineoplastic (hormonal) tranquilizer, neuroleptic, alpha adrenergic blocker Orally active progesteron with antiandrogenic activity; has been used in combinations as an oral contraceptive. Progestogen; antineoplastic (hormonal).
• Therapeutic Function: Progestin

Technology Process of [(10R,13S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate

There total 19 articles about [(10R,13S,17R)-17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] 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: 97.8%

6-chloro-17-hydroxypregna-4,6-diene-3,20-dione (1961-77-9) + acetic anhydride (108-24-7) → chlormadinone acetate (302-22-7)

Guidance literature:

With toluene-4-sulfonic acid; acetic acid; In chloroform; at 40 - 45 ℃; Solvent;

Reference yield: 91.18%

17α-acetoxy-6α,7α-epoxy-4-pregnen-3,20-dione (2133-50-8) → chlormadinone acetate (302-22-7)

Guidance literature:

With hydrogenchloride; In acetic acid; for 24h;

Reference yield: 54.0%

7α-azido-6β-chloro-3,20-dioxopregn-4-en-17α-yl acetate → chlormadinone acetate (302-22-7)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 3h;

upstream raw materials:

17α-acetoxy-6α-chloropregn-4-ene-3,20-dione

6-chloro-3-methoxy-17α-hydroxypregna-3,5-dien-20-one 17-acetate

17-acetoxy-3-ethoxy-pregna-3,5-dien-20-one

17α-acetoxy-6β-chloropregn-4-ene-3,20-dione

Downstream raw materials:

6-chloropregna-4,6-diene-3β,17α-diol-20-one 17-acetate

6-chloro-17-hydroxypregna-4,6-diene-3,20-dione

6-chloro-17a-acetoxy-pregnane-1,4,6-,triene-3,20-dione

Refernces

• 1、 -. "Preparation method of chlormadinone acetate". Paragraph 0016; 0019; 0022. . Retrieved 2018/03/09.
• 2、 -. "Further syntheses of cyproterone acetate". Page/Page column 3; 18; 30; 32. . Retrieved 2010/02/07.