Chlormadinone

Base Information

• Chemical Name: Chlormadinone
• CAS No.: 1961-77-9
• Molecular Formula: C21H27 Cl O3
• Molecular Weight: 362.897
• European Community (EC) Number: 217-802-3
• UNII: SDS4N642GG
• DSSTox Substance ID: DTXSID3022796
• Nikkaji Number: J13.853C
• Wikipedia: Chlormadinone
• Wikidata: Q905012
• NCI Thesaurus Code: C83620
• Metabolomics Workbench ID: 154326
• ChEMBL ID: CHEMBL1697830
• Mol file: 1961-77-9.mol

Synonyms:Chlormadinon Acetate;Chlormadinone;Chlormadinone Acetate;Chlormadinone Acetate, (9 beta,10 alpha)-Isomer;Neo Eunomin;Neo-Eunomin;NeoEunomin;Pregna-4,6-diene-3,20-dione, 17-(acetyloxy)-6-chloro-

Chemical Property of Chlormadinone

Chemical Property:

• Vapor Pressure: 2.18E-12mmHg at 25°C
• Melting Point: 213°C
• Refractive Index: 1.582
• Boiling Point: 506.7 °C at 760 mmHg
• PKA: 12.87±0.70(Predicted)
• Flash Point: 260.2 °C
• PSA: 54.37000
• Density: 1.24 g/cm³
• LogP: 4.18090
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 362.1648724
• Heavy Atom Count: 25
• Complexity: 723

Purity/Quality:

98%,99%, ^*data from raw suppliers

Chlormadinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(=O)CCC34C)Cl)C)O
• Isomeric SMILES: CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=C(C4=CC(=O)CC[C@]34C)Cl)C)O
• Recent NIPH Clinical Trials: The placebo-controlled parallel-group comparative study for patients with low-risk prostate cancer
• Uses: CHLORMADINON has been used in combinations as an oral contraceptive. It has been used in combinations as an oral contraceptive.

Technology Process of Chlormadinone

There total 8 articles about Chlormadinone 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: 85.0%

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

Guidance literature:

With sodium hydroxide; sodium perchlorate; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0039-128X(02)00050-8

Reference yield:

(6R,7S,8R,9S,10R,13S,14S,17R)-17-Acetyl-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-20-oxa-cyclopropa[6,7]cyclopenta[a]phenanthren-3-one → 6-chloro-17-hydroxypregna-4,6-diene-3,20-dione (1961-77-9)

Guidance literature:

With hydrogenchloride; acetic acid; In 1,4-dioxane;

Reference yield:

17-hydroxyprogesterone (68-96-2) → 6-chloro-17-hydroxypregna-4,6-diene-3,20-dione (1961-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1: bromine; acetic acid; hydrogen bromide / 1,4-dioxane / 25 - 30 °C

2: lithium bromide; lithium carbonate / N,N-dimethyl-formamide / 50 - 90 °C

3: Perbenzoic acid / ethyl acetate / 20 - 25 °C

4: hydrogenchloride; acetic acid / water / 40 - 45 °C / Sealed tube

With hydrogenchloride; Perbenzoic acid; hydrogen bromide; bromine; lithium carbonate; acetic acid; lithium bromide; In 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

chlormadinone acetate

17-hydroxyprogesterone

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

Downstream raw materials:

chlormadinone acetate

Refernces

• 1、 Cabeza, Marisa,Zambrano, Armando,Heuze, Ivonne,Carrizales, Erick,Palacios, Anay,Segura, Tania,Valencia, Norma,Bratoeff, Eugene. "Novel C-6 substituted and unsubstituted pregnane derivatives as 5α-reductase inhibitors and their effect on hamster flank organs diameter size". experimental part. p. 793 - 802. Retrieved 2009/12/01.
• 2、 -. "Combined antiestrogens and antigonadotropically effective antiandrogens for the prophylaxis and therapy of hyperplasia of the prostate". . . Retrieved 2008/06/13.