Norbolethone

Base Information

• Chemical Name: Norbolethone
• CAS No.: 797-58-0
• Molecular Formula: C21H32 O2
• Molecular Weight: 316.53
• NSC Number: 89791
• UNII: U3BZU2241A,O60979L83F
• DSSTox Substance ID: DTXSID50154027,DTXSID801015371
• Nikkaji Number: J69.163A
• Wikipedia: Norboletone
• Wikidata: Q410981
• NCI Thesaurus Code: C90642
• Metabolomics Workbench ID: 38799
• ChEMBL ID: CHEMBL2105134
• Mol file: 797-58-0.mol

Synonyms:13-EHDPO;13-ethyl-17-hydroxy-18,19-dinor-17-pregn-4-en-20-yn-3-one;norbolethone

Chemical Property of Norbolethone

Chemical Property:

• Vapor Pressure: 2.24E-10mmHg at 25°C
• Refractive Index: 1.5344 (estimate)
• Boiling Point: 459.5°C at 760 mmHg
• Flash Point: 195.6°C
• PSA: 37.30000
• Density: 1.09g/cm³
• LogP: 4.65940
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 316.240230259
• Heavy Atom Count: 23
• Complexity: 536

Purity/Quality:

99% ^*data from raw suppliers

Norbolethone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCC3C(C1CCC2(CC)O)CCC4=CC(=O)CCC34
• Isomeric SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(CC)O)CCC4=CC(=O)CC[C@H]34

Technology Process of Norbolethone

There total 37 articles about Norbolethone 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:

2-ethylcyclopentane-1,3-dione (823-36-9) → DL-17β-Hydroxy-13β.17α-diethyl-gon-4-en-3-on (797-58-0,797-59-1,1235-15-0,17092-12-5,19707-55-2,24211-89-0,28439-19-2,101053-14-9)

Guidance literature:

Multi-step reaction with 10 steps

1: triethylenediamine / xylene

2: aq. HCl / methanol

3: NaBH₄ / methanol

4: H₂ / Raney-Ni / dioxane

5: Li, liq. NH₃ / diethyl ether; dioxane

6: CrO₃, aq. H₂SO₄ / acetone

7: Li, H₂NCH₂CH₂NH₂ / tetrahydrofuran

8: H₂ / Pd-C / tetrahydrofuran

9: Li, liq. NH₃ / tetrahydrofuran

10: aq. HCl / methanol; tetrahydrofuran

With 1,4-diaza-bicyclo[2.2.2]octane; chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; sulfuric acid; ammonia; hydrogen; lithium; ethylenediamine; palladium on activated charcoal; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; acetone; xylene;

DOI:10.1248/cpb.13.1289

Reference yield:

(+/-)-13-ethyl-3-methoxygona-1,3,5(10),8,14-pentaen-17-one (848-07-7) → DL-17β-Hydroxy-13β.17α-diethyl-gon-4-en-3-on (797-58-0,797-59-1,1235-15-0,17092-12-5,19707-55-2,24211-89-0,28439-19-2,101053-14-9)

Guidance literature:

Multi-step reaction with 8 steps

1: NaBH₄ / methanol

2: H₂ / Raney-Ni / dioxane

3: Li, liq. NH₃ / diethyl ether; dioxane

4: CrO₃, aq. H₂SO₄ / acetone

5: Li, H₂NCH₂CH₂NH₂ / tetrahydrofuran

6: H₂ / Pd-C / tetrahydrofuran

7: Li, liq. NH₃ / tetrahydrofuran

8: aq. HCl / methanol; tetrahydrofuran

With chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; sulfuric acid; ammonia; hydrogen; lithium; ethylenediamine; palladium on activated charcoal; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; acetone;

DOI:10.1248/cpb.13.1289

Reference yield:

2-[2-(3,4-dihydro-6-methoxy-1(2H)-naphthalenylidene)ethyl]-2-ethyl-1,3-cyclopentanedione (850-92-0) → DL-17β-Hydroxy-13β.17α-diethyl-gon-4-en-3-on (797-58-0,797-59-1,1235-15-0,17092-12-5,19707-55-2,24211-89-0,28439-19-2,101053-14-9)

Guidance literature:

Multi-step reaction with 9 steps

1: aq. HCl / methanol

2: NaBH₄ / methanol

3: H₂ / Raney-Ni / dioxane

4: Li, liq. NH₃ / diethyl ether; dioxane

5: CrO₃, aq. H₂SO₄ / acetone

6: Li, H₂NCH₂CH₂NH₂ / tetrahydrofuran

7: H₂ / Pd-C / tetrahydrofuran

8: Li, liq. NH₃ / tetrahydrofuran

9: aq. HCl / methanol; tetrahydrofuran

With chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; sulfuric acid; ammonia; hydrogen; lithium; ethylenediamine; palladium on activated charcoal; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; acetone;

DOI:10.1248/cpb.13.1289

upstream raw materials:

ethylmagnesium bromide

dl-3-methoxy-13β-ethylgona-2,5(10)-dien-17-one

norgestrel

dl-3-methoxy-13β-ethylgona-2,5(10)-dien-17β-ol

Refernces

• 1、 -. "Synthesis of 13-alkyl-gon-4-ones". . . Retrieved 2008/06/13.
• 2、 SMITH,HUGHES,DOUGLAS,HARTLEY,MCLOUGHLIN,SIDDALL,WENDT,BUZBY Jr.,HERBST,LEDIG,MCMENAMIN,PATTISON,SUIDA,TOKOLICS,EDGREN,JANSEN,GADSBY,WATSON,PHILLIPS. "TOTALLY SYNTHETIC -13-ALKYL-3-HYDROXY AND". . p. 394 - 396. Retrieved 2007/10/12.