13-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-ol

Base Information

• Chemical Name: 13-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-ol
• CAS No.: 7443-72-3
• Molecular Formula: C20H26O2
• Molecular Weight: 298.425
• European Community (EC) Number: 231-188-4
• DSSTox Substance ID: DTXSID901210372
• Nikkaji Number: J278.847K
• Wikidata: Q72475717
• Mol file: 7443-72-3.mol

Synonyms:7443-72-3;13-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-ol;EINECS 231-188-4;(17beta)-13-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17-ol;(13S,14S,17S)-13-ethyl-3-methoxy-6,7,11,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-17-ol;SCHEMBL8053086;DTXSID901210372;Gona-1,3,5(10),8-tetraen-17-ol, 13-ethyl-3-methoxy-, (17b)-;17beta-hydroxy-3-methoxy-estra-1,3,5(10),8(9)-tetraen-18-methyl-17-ol;AKOS016008795;A865895;13-Ethyl-3-methoxygona-1,3,5(10),8-tetren-17beta-ol;3-methoxy-18-methyl-1,3,5(10),8-estratetraen-17beta-ol;13beta-ethyl-3-methoxy-gona-1,3,5(10),8-tetraen-17beta-ol;13beta-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-ol;13beta-ethyl-3-methoxy-gona-1,3,5(10), 8-tetraen-17beta-ol

Chemical Property of 13-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-ol

Chemical Property:

• Vapor Pressure: 6.77E-09mmHg at 25°C
• Melting Point: 102-105 °C(Solv: acetonitrile (75-05-8))
• Refractive Index: 1.592
• Boiling Point: 450.3 °C at 760 mmHg
• PKA: 15.01±0.40(Predicted)
• Flash Point: 199.7 °C
• PSA: 29.46000
• Density: 1.14 g/cm³
• LogP: 4.35610
• Storage Temp.: 2-8°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 298.193280068
• Heavy Atom Count: 22
• Complexity: 468

Purity/Quality:

99% ^*data from raw suppliers

(17β)-13-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCC3=C(C1CCC2O)CCC4=C3C=CC(=C4)OC
• Isomeric SMILES: CC[C@]12CCC3=C([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)OC
• Uses: (17β)-13-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17-ol is a reactant in the synthesis of new immunogens for levonorgestrel and its 3-syn and anti-oximes.

Technology Process of 13-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-ol

There total 13 articles about 13-Ethyl-3-methoxygona-1,3,5(10),8-tetraen-17beta-ol 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: 98.0%

(13S,14S)-13-ethyl-3-methoxy-6,7,11,12,13,14,15,16-octahydro-cyclopenta[a]phenanthren-17-one (38393-52-1) → 18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol (7443-72-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 0.0833333h; Ambient temperature; ultrasound;

DOI:10.1002/hlca.19950780524

Reference yield:

2-ethylcyclopentane-1,3-dione (823-36-9) → 18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol (7443-72-3)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylenediamine / xylene

2: aq. HCl / methanol

3: NaBH₄ / methanol

4: H₂ / Raney-Ni / dioxane

5: Py

6: KOH / methanol

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; hydrogen; nickel; In 1,4-dioxane; methanol; 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) → 18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol (7443-72-3)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / methanol

2: H₂ / Raney-Ni / dioxane

3: Py

4: KOH / methanol

With pyridine; potassium hydroxide; sodium tetrahydroborate; hydrogen; nickel; In 1,4-dioxane; methanol;

DOI:10.1248/cpb.13.1289

upstream raw materials:

13β-ethyl-3-methoxygona-1,3,5(10)8-tetraen-17β-yl acetate

(13S,14S)-13-ethyl-3-methoxy-6,7,11,12,13,14,15,16-octahydro-cyclopenta[a]phenanthren-17-one

l-3-Methoxy-13β-ethyl-gona-1,3,5(10),8-tetraen-17β-ol-hydrogensuccinat

13β-Aethyl-3-methoxy-gonapentaen-(1.3.5(10).8.14)-ol-(17β)-acetat

Downstream raw materials:

17β-benzyloxy-D-13β-ethyl-11α-hydroxy-3-methoxy-estra-1,3,5(10)-triene

17β-benzyloxy-D-13β-ethyl-3-methoxy-estra-1,3,5(10)-triene-11-one

13β-ethyl-gon-4-en-3,17-dione

13β-Ethyl-17β-(3-phenylpropionoxy)-gon-4-en-3-one

Refernces

• 1、 Rufer,Kosmol,Schr?der,Kleslich,Gibian. "Total synthesis of optically active 13-ethyl-gonane derivatives". . p. 141 - 148. Retrieved 2007/10/13.
• 2、 Hiraga. "Syntheses of racemic and optically active 13-beta-ethylgonanes.". . p. 1289 - 1294. Retrieved 2007/10/13.