3-Deoxyestrone

Base Information

• Chemical Name: 3-Deoxyestrone
• CAS No.: 53-45-2
• Molecular Formula: C18H22 O
• Molecular Weight: 254.372
• NSC Number: 22195
• UNII: M8WJ87C2AC
• DSSTox Substance ID: DTXSID4022498
• Nikkaji Number: J79.401E
• Wikidata: Q27148579
• ChEMBL ID: CHEMBL1627698
• Mol file: 53-45-2.mol

Synonyms:3-deoxyestrone

Chemical Property of 3-Deoxyestrone

Chemical Property:

• Vapor Pressure: 3.4E-06mmHg at 25°C
• Boiling Point: 387°Cat760mmHg
• Flash Point: 167.8°C
• PSA: 17.07000
• Density: 1.088g/cm³
• LogP: 4.11180
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 254.167065321
• Heavy Atom Count: 19
• Complexity: 387

Purity/Quality:

99% ^*data from raw suppliers

1,3,5(10)-ESTRATRIEN-17-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CCC4=CC=CC=C34
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=CC=CC=C34

Technology Process of 3-Deoxyestrone

There total 20 articles about 3-Deoxyestrone 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: 97.0%

C20H27NO3S → 3-deoxyestrone (53-45-2)

Guidance literature:

With potassium phosphate; 4,5-dimethyl-1,3-bis-(2,4,6-trimethylphenyl)-3H-imidazol-1-ium chloride; C₄₆H₃₉ClNiP₂; isopropyl alcohol; In toluene; at 80 ℃; for 15.15h;

DOI:10.1055/a-1548-8362

Reference yield: 97.0%

estrone triflate (92817-04-4) → 3-deoxyestrone (53-45-2)

Guidance literature:

With triethylsilane; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; In N,N-dimethyl-formamide; at 90 ℃; for 2h; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.5b09308

Reference yield: 96.0%

(8R,9S,13S,14S)-3-(1,1-Dioxo-1H-1λ6-benzo[d]isothiazol-3-yloxy)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one (132636-60-3) → 3-deoxyestrone (53-45-2) + saccharin (81-07-2)

Guidance literature:

With sodium hypophosphite; palladium on activated charcoal; In water; benzene; for 0.25h; Heating;

DOI:10.1016/S0040-4039(00)97960-7

upstream raw materials:

Estrone

estrone triflate

(8R,9S,13S,14S)-3-(1,1-Dioxo-1H-1λ⁶-benzo[d]isothiazol-3-yloxy)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

<(1-phenyl-1H-tetrazol-5-yl)oxy>estra-1,3,5(10)-trien-17-one

Downstream raw materials:

C₂₄H₂₇NO

C₂₄H₂₈BrNO

N-Benzylestra-1,3,5(10)-trien-17β-amine

17α-Aethinyl-oestra-1,3,5(10)-trien-17β-ol

Refernces

• 1、 Bydal, Patrick,Luu-The, Van,Labrie, Fernand,Poirier, Donald. "Steroidal lactones as inhibitors of 17β-hydroxysteroid dehydrogenase type 5: Chemical synthesis, enzyme inhibitory activity, and assessment of estrogenic and androgenic activities". . p. 632 - 644. Retrieved 2009.
• 2、 Nambara,Numazawa. "Metabolites of 3-desoxyestrone in rabbit urine.". . p. 383 - 384. Retrieved 1968.
• 3、 Korvinson, Kirill A.,Akula, Hari K.,Malinchak, Casina T.,Sebastian, Dellamol,Wei, Wei,Khandaker, Tashrique A.,Andrzejewska, Magdalena R.,Zajc, Barbara,Lakshman, Mahesh K.. "Catalytic Reductions Without External Hydrogen Gas: Broad Scope Hydrogenations with Tetrahydroxydiboron and a Tertiary Amine". . p. 166 - 176. Retrieved 2020/01/02.
• 4、 Xi, Xiaoxiang,Chen, Tieqiao,Zhang, Ji-Shu,Han, Li-Biao. "Efficient and selective hydrogenation of C-O bonds with a simple sodium formate catalyzed by nickel". . p. 1521 - 1524. Retrieved 2018/02/19.