19-Norpregn-4-ene-3,20-dione, 21-hydroxy-

Base Information

• Chemical Name: 19-Norpregn-4-ene-3,20-dione, 21-hydroxy-
• CAS No.: 4682-70-6
• Molecular Formula: C20H28O3
• Molecular Weight: 316.4345
• DSSTox Substance ID: DTXSID90963675
• Nikkaji Number: J417.519K
• Wikidata: Q82945555
• Mol file: 4682-70-6.mol

Synonyms:19-nordeoxycorticosterone

Chemical Property of 19-Norpregn-4-ene-3,20-dione, 21-hydroxy-

Chemical Property:

• Vapor Pressure: 1.13E-11mmHg at 25°C
• Boiling Point: 490.4°Cat760mmHg
• Flash Point: 264.5°C
• PSA: 54.37000
• Density: 1.17g/cm³
• LogP: 3.30580
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 316.20384475
• Heavy Atom Count: 23
• Complexity: 563

Purity/Quality:

19-Nordeoxycorticosterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2C(=O)CO)CCC4=CC(=O)CCC34
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)CO)CCC4=CC(=O)CC[C@H]34
• Uses: Corticosterone derivative/degradation product. 19-Nordeoxycorticosterone can be used in biological study of correlation between pregnanesteroid conformation, renal mineralocorticoid receptor affinity, and anti-natriuretic effect.

Technology Process of 19-Norpregn-4-ene-3,20-dione, 21-hydroxy-

There total 64 articles about 19-Norpregn-4-ene-3,20-dione, 21-hydroxy- 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%

(+)-11-deoxy-19-corticosterone benzoate (135399-04-1) → 19-Nordeoxycorticosterone (4682-70-6)

Guidance literature:

With methanol; water; potassium carbonate; In dichloromethane; for 1.33333h;

Reference yield: 10.0%

19-nordeoxycorticosterone 3,20-bis(1,3-propanedithiyl acetal) (74824-66-1) → 19-Nordeoxycorticosterone (4682-70-6)

Guidance literature:

With calcium carbonate; mercury dichloride; In methanol; water; for 5h; Heating;

DOI:10.1021/jo01310a028

Reference yield:

Pregnenolone acetate (1778-02-5) → 19-Nordeoxycorticosterone (4682-70-6)

Guidance literature:

Multi-step reaction with 9 steps

1: hypobromous acid

2: Pb(OAc)4, I₂ / Irradiation

3: hydrolysis

4: 1.) BF₃*Et₂O / 1.) C₆H₆, MeOH, room temperature, 20 min, 2.) 5 h

5: Jones reagent / acetone / 5 °C

6: NaOAc / methanol / 1 h / Heating

7: 111 mg / Zn, AcOH / propan-2-ol / 3 h / Heating

8: 55 mg / pyridinuim chlorochromate / CH₂Cl₂ / 0.5 h / Ambient temperature

9: 20 mg / KOH / methanol / 1 h / Heating

With lead(IV) acetate; potassium hydroxide; jones reagent; boron trifluoride diethyl etherate; iodine; sodium acetate; hypobromous acid; acetic acid; pyridinium chlorochromate; zinc; In methanol; dichloromethane; isopropyl alcohol; acetone;

upstream raw materials:

19-norprogesterone

21-acetoxy-19-nor-pregn-4-ene-3,20-dione

19-oxo-11-deoxycorticosterone acetate

(+)-11-deoxy-19-corticosterone benzoate

Refernces

• 1、 Sandoval et al.. "-". . p. 148,151. Retrieved 1955.
• 2、 Nemoto, Hideo,Satoh, Atsushi,Ando, Masahiro,Fukumoto, Keiichiro. "A Practical Route for Enantioselective Total Synthesis of (+)-11-Deoxy-19-norcorticosterone via Intramolecular Diels-Alder Addition to an ortho-Quinodimethane". . p. 1309 - 1314. Retrieved 2007/10/02.
• 3、 Terasawa,Okada. "Convenient preparative routes to 19-hydroxy, 19-oxo-, 19-oic-, and 19-nor-deoxycorticosterone". . p. 537 - 545. Retrieved 2007/10/02.