Methoxydienone

Base Information

• Chemical Name: Methoxydienone
• CAS No.: 2322-77-2
• Molecular Formula: C20H28O2
• Molecular Weight: 300.441
• European Community (EC) Number: 219-034-4,228-351-7
• UNII: 12AU99WIMP
• DSSTox Substance ID: DTXSID201036347,DTXSID001045120
• Nikkaji Number: J213.193E
• Wikipedia: Methoxydienone
• Wikidata: Q27251400
• Mol file: 2322-77-2.mol

Synonyms:METHOXYDIENONE;13-beta-Ethyl-3-methoxygona-2,5(10)-dien-17-one;(8r,9s,13s,14s)-13-ethyl-3-methoxy-4,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-one;13-Ethyl-3-methoxy-gona-2,5(10;D(-)-18-METHYL-3-METHOXY-ESTRA-2,5(10)-DIEN-17-ONE;METHOXYDIENONE(13-BETA-ETHYL-3-METHOXYGONA-2,5(10)-DIEN-17-ONE);18-Methylestra-2,5(10)-dien-3-ol-17-one-3-methy ether;3-Methoxy-18-methylestra-2,5(10)-dien-17-one

Chemical Property of Methoxydienone

Chemical Property:

• Appearance/Colour: White to Off-White Crystalline Powder
• Vapor Pressure: 3.21E-08mmHg at 25°C
• Melting Point: ≥170oC
• Refractive Index: 1.551
• Boiling Point: 448 °C at 760 mmHg
• Flash Point: 188.8 °C
• PSA: 26.30000
• Density: 1.09 g/cm³
• LogP: 4.80260
• Water Solubility.: 270μg/L at 20℃
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 300.208930132
• Heavy Atom Count: 22
• Complexity: 556

Purity/Quality:

99% ^*data from raw suppliers

MaxLMG ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCC3C(C1CCC2=O)CCC4=C3CC=C(C4)OC
• Isomeric SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3CC=C(C4)OC
• Uses: Max LMG is a progestin derived steroid and not a 17-alpha alkylated steroid. Max LMG is structurally related to RU-486 and acts as an antiprogesterone, decreasing estrogen-like effects.

Technology Process of Methoxydienone

There total 21 articles about Methoxydienone 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: 85.0%

D-13β-ethyl-17β-hydroxy-3-methoxy-gona-2,5(10)-diene (14507-49-4) → 13β-ethyl-3-methoxygona-2,5(10)-diene-17-one (2322-77-2)

Guidance literature:

With sulfur trioxide pyridine complex; In dimethyl sulfoxide; triethylamine; Ambient temperature;

Reference yield: 76.0%

dl-3-methoxy-13β-ethylgona-2,5(10)-dien-17β-ol (1038-28-4,5772-35-0,14507-49-4,77209-48-4,85798-56-7) → dl-3-methoxy-13β-ethylgona-2,5(10)-dien-17-one (2322-77-2,6236-40-4,17092-08-9,19640-64-3)

Guidance literature:

With molecular sieve; aluminum isopropoxide; butanone; In benzene;

DOI:10.1002/hlca.19850680430

Reference yield:

2-Ethyl-3-vinyl-cyclopentanone → dl-3-methoxy-13β-ethylgona-2,5(10)-dien-17-one (2322-77-2,6236-40-4,17092-08-9,19640-64-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent NaH, Et₃N / 1,2-dimethoxy-ethane; paraffin / 1.) 3.5 h, reflux; 2.) 40 min

2: 1.) 2,4,6-trimethylphenol, pyridine; 2.) oxalic acid / 1.) methylcyclohexane, 13.5 h, 98 deg C, irradiation

3: 99 percent / LiAlH₄ / diethyl ether

4: 62 percent / K, aniline, NH₃ / tetrahydrofuran / 1 h

5: 76 percent / 2-butanone, aluminium isopropylate, mol. sieve / benzene

With pyridine; lithium aluminium tetrahydride; molecular sieve; Mesitol; ammonia; oxalic acid; aluminum isopropoxide; sodium hydride; triethylamine; aniline; butanone; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; paraffin; benzene;

DOI:10.1002/hlca.19850680430

upstream raw materials:

D-13β-ethyl-17β-hydroxy-3-methoxy-gona-2,5(10)-diene

18-methyl-3-methoxy-1,3,5(10),8-estratetraen-17β-ol

2-Trimethylsilyl-1-(4-methoxy-2-methylphenyl)prop-2-en-1-on

13-Ethyl-3-methoxy-6,7:8,9-disecogona-1,3,5⁽¹⁰⁾,7-tetraen-9,17-dion

Downstream raw materials:

DL-17β-Hydroxy-13β.17α-diethyl-gon-4-en-3-on

D-17β-acetoxy-13β-ethyl-17α-ethynyl-gon-4-en-3-one

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

17beta-hydroxy-18-methyl-4-estren-3-one

Refernces

• 1、 Quinkert,Del Grosso,Doring,Doring,Schenkel,Bauch,Dambacher,Bats,Zimmermann,Durner. "Total synthesis with a chirogenic opening move demonstrated on steroids with estrane or 18a-homoestrane skeleton". . p. 1345 - 1391. Retrieved 2007/10/02.
• 2、 Baier,Durner,Quinkert. "Total-synthesis of (-)-norgestrel". . p. 1054 - 1068. Retrieved 2007/10/02.