19-Norprogesterone

Base Information

• Chemical Name: 19-Norprogesterone
• CAS No.: 472-54-8
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.441
• NSC Number: 22021
• UNII: 1A5185976G
• DSSTox Substance ID: DTXSID40197064
• Nikkaji Number: J11.976H
• Wikipedia: 19-Norprogesterone
• Wikidata: Q4557698
• NCI Thesaurus Code: C29782
• Pharos Ligand ID: FYM7T8LHSUHU
• ChEMBL ID: CHEMBL284109
• Mol file: 472-54-8.mol

Synonyms:19-norprogesterone;19-norprogesterone, (14beta,17alpha)-isomer;19-norprogesterone, (9beta,10alpha)-isomer

Chemical Property of 19-Norprogesterone

Chemical Property:

• Vapor Pressure: 3.38E-08mmHg at 25°C
• Melting Point: 144.5°C
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 447.4°Cat760mmHg
• Flash Point: 166.8°C
• PSA: 34.14000
• Density: 1.1g/cm³
• LogP: 4.33340
• Water Solubility.: 36.1mg/L(37 oC)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 300.208930132
• Heavy Atom Count: 22
• Complexity: 546

Purity/Quality:

99% ^*data from raw suppliers

19-Norprogesterone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C
• Uses: 19-Norprogesterone is a close analogue of the steroid progesterone.

Technology Process of 19-Norprogesterone

There total 33 articles about 19-Norprogesterone 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: 90.0%

C20H30O2 → 19-norprogesterone (472-54-8)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 20 - 25 ℃; for 3h; Inert atmosphere;

Reference yield:

(Z)-3,20-dimethoxy-21-hydroxy-19-norpregna-1,3,5(10),17(20)-tetraene (65078-08-2) → 19-norprogesterone (472-54-8) + 19-Nordeoxycorticosterone (4682-70-6)

Guidance literature:

With ammonia; oxalic acid; lithium; Yield given. Multistep reaction. Yields of byproduct given; 1.) EtOH, Et₂O-THF, -75 deg C, 0.5 h, 2.) aq. MeOH, 50 deg C, 2 h; room temp. overnight;

DOI:10.1016/S0040-4020(01)87452-4

Reference yield:

17-hydroxy-17-cyanoestr-4-en-3-one (17006-06-3) → 19-norprogesterone (472-54-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.1 g / phosphorus oxychloride / pyridine / Heating

2: 170 mg / hydrogen / palladium-on-charcoal / ethyl acetate / 0.17 h / 760 Torr

With hydrogen; trichlorophosphate; palladium on activated charcoal; In pyridine; ethyl acetate;

DOI:10.1021/jo01310a028

upstream raw materials:

3-ethoxy-17β-acetoxy-19-nor-3,5-pregnadien-20-one

methyl magnesium iodide

17β-cyanoestr-4-en-3-one

(Z)-3,20-dimethoxy-21-hydroxy-19-norpregna-1,3,5⁽¹⁰⁾,17⁽²⁰⁾-tetraene

Downstream raw materials:

Δ^3,5-19-Norpregnadien-20-on

20β-hydroxy-19-nor-4-pregnen-3-one

19-Nordeoxycorticosterone

20α_F-hydroxy-19-nor-pregn-4-en-3-one

Refernces

• 1、 Djerassi et al.. "". . p. 4440. Retrieved 1953.
• 2、 Terasawa,Okada. "Convenient preparative routes to 19-hydroxy, 19-oxo-, 19-oic-, and 19-nor-deoxycorticosterone". . p. 537 - 545. Retrieved 2007/10/02.
• 3、 -. "Process for the preparation of steroid oxiranes". . . Retrieved 2008/06/13.