9,17-Dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid

Base Information

• Chemical Name: 9,17-Dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid
• CAS No.: 1944-63-4
• Molecular Formula: C13H18 O4
• Molecular Weight: 238.284
• Hs Code.: 2918300090
• European Community (EC) Number: 435-830-6
• DSSTox Substance ID: DTXSID20472225
• Metabolomics Workbench ID: 62931
• Nikkaji Number: J974.618H
• Wikidata: Q27132766
• Mol file: 1944-63-4.mol

Synonyms:9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid;DOHN acid

Chemical Property of 9,17-Dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid

Chemical Property:

• PSA: 71.44000
• LogP: 1.81570
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 238.12050905
• Heavy Atom Count: 17
• Complexity: 374

Purity/Quality:

99.9% ^*data from raw suppliers

1,5-Dioxo-7aβ-methyl-3aα-hexahydroindane-4α-propionicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(=O)C(C1CCC2=O)CCC(=O)O
• Isomeric SMILES: C[C@]12CCC(=O)[C@H]([C@@H]1CCC2=O)CCC(=O)O
• Uses: 1,5-Dioxo-7aβ-methyl-3aα-hexahydroindane-4α-propionic Acid, can be used for the novel and concise synthesis of 19-Nor-10-azasteroids, a new class of steroid 5α-reductase inhibitors.

Technology Process of 9,17-Dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid

There total 13 articles about 9,17-Dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid 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: 40.0%

C13H18O3 → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 18h;

DOI:10.1002/ejoc.201500698

Reference yield:

(S)-Halos-Parish ketone (17553-86-5) → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere

2.1: 1-methyl-1H-imidazole; iodine / tetrahydrofuran / 42 h / 20 °C / Inert atmosphere

3.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere

3.2: 18 h / 20 °C / Inert atmosphere

4.1: palladium on activated charcoal; hydrogen

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C

7.1: periodic acid / ethyl acetate / 20 °C

8.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C

With 1-methyl-1H-imidazole; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; palladium on activated charcoal; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; dimethyl sulfoxide; periodic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethanol; water; dimethyl sulfoxide; ethyl acetate; mineral oil; tert-butyl alcohol;

DOI:10.1002/ejoc.201500698

Reference yield:

(1S,7aS)-1-hydroxy-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one (16271-49-1) → 3aα-H-4α-(3’-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (1944-63-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2.1: dimethyl sulfoxide; sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere

2.2: 18 h / 20 °C / Inert atmosphere

3.1: palladium on activated charcoal; hydrogen

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C

6.1: periodic acid / ethyl acetate / 20 °C

7.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 18 h / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; palladium on activated charcoal; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; dimethyl sulfoxide; periodic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; mineral oil; tert-butyl alcohol;

DOI:10.1002/ejoc.201500698

upstream raw materials:

[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-magnesium chloride

C₁₈H₂₆O₅

(1R,3aS,4S,7aS)-4-(2-Carboxy-ethyl)-1-hydroxy-7a-methyl-5-oxo-octahydro-indene-1-carboxylic acid

(S)-Halos-Parish ketone

Downstream raw materials:

(3aS,7aS)-4α-ethenyl-1-oxo-5-(4'-methylbenzenesulfonyl)-3a,4,5,6,7,7a-hexahydro-7a-methylindan

estradiol

Refernces

• 1、 Cooper, Gary F.,Van Horn, Albert R.. "A SHORT EFFICIENT SYNTHESIS OF 19-NORANDROST-4-ENE-3,17-DIONE". . p. 1479 - 1482. Retrieved 2007/10/02.
• 2、 Lee,Sih. "Mechanisms of steroid oxidation by microorganisms. XII. Metabolism of hexahydroindanpropionic acid derivatives.". . p. 1395 - 1403. Retrieved 2007/10/11.