5-(5,7-dichloro-2-oxo-1H-indol-3-ylidene)-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one

Base Information

• Chemical Name: 5-(5,7-dichloro-2-oxo-1H-indol-3-ylidene)-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS No.: 6544-68-9
• Molecular Formula: C19H24O2
• Molecular Weight: 284.398
• DSSTox Substance ID: DTXSID10425745
• Wikidata: Q72490529
• Mol file: 6544-68-9.mol

Synonyms:6544-68-9;5-(5,7-dichloro-2-oxo-1H-indol-3-ylidene)-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one;5,7-dichloro-3-(3-ethyl-4-hydroxy-2-sulfanylidene-1,3-thiazol-5-yl)indol-2-one;AGN-PC-0LRELL;Oprea1_064574;SCHEMBL17830763;DTXSID10425745;AKOS034454259;Z56783891

Chemical Property of 5-(5,7-dichloro-2-oxo-1H-indol-3-ylidene)-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one

Chemical Property:

• Melting Point: 255 °C(Solv: acetone (67-64-1))
• Refractive Index: 1.77
• Boiling Point: 456.2 °C at 760 mmHg
• PKA: 10.25±0.40(Predicted)
• Flash Point: 194.3 °C
• PSA: 37.30000
• Density: 1.138 g/cm³
• LogP: 4.20750
• Solubility.: Acetonitrile, DCM
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 357.9404252
• Heavy Atom Count: 21
• Complexity: 747

Purity/Quality:

99% ^*data from raw suppliers

18a-Methylestrone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C(=C(SC1=S)C2=C3C=C(C=C(C3=NC2=O)Cl)Cl)O
• Uses: 18a-Methylestrone is an reactant in the synthesis of 2-methoxyestradiol (M262625), a natural metabolite of 17β-Estradiol which is devoid of estrogenic activity.

Technology Process of 5-(5,7-dichloro-2-oxo-1H-indol-3-ylidene)-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one

There total 15 articles about 5-(5,7-dichloro-2-oxo-1H-indol-3-ylidene)-3-ethyl-2-sulfanylidene-1,3-thiazolidin-4-one 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: 82.1%

13β-ethyl-gon-4-en-3,17-dione (21800-83-9) → 13β-ethyl-3-hydroxygona-1,3,5(10)-trien-17-one (6544-68-9)

Guidance literature:

With copper(ll) bromide; In acetonitrile; for 16h; Ambient temperature;

DOI:10.1016/0039-128X(94)90017-5

Reference yield: 75.0%

D-(+)-13β-ethylgon-4-ene-3,17-dione → 13β-ethyl-3-hydroxygona-1,3,5(10)-trien-17-one (6544-68-9)

Guidance literature:

With lithium bromide; copper(ll) bromide; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/S0039-128X(99)00084-7

Reference yield:

13-Ethyl-3-hydroxy-6,7,11,12,13,16-hexahydro-cyclopenta[a]phenanthren-17-one (845-89-6) → (+/-)-13β-Ethyl-3-hydroxy-8α-gona-1,3,5(10)-trien-17-on (845-85-2,845-86-3,845-87-4,2445-29-6,6544-68-9,20302-04-9,26788-32-9,34990-81-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jm00321a016

upstream raw materials:

13β-ethyl-gon-4-en-3,17-dione

dl-13-ethyl-3-methoxygona-1,3,5⁽¹⁰⁾-trien-17-one

levonorgestrel

levonorgestrel

Downstream raw materials:

dl-3-Benzyloxy-13β-aethylgona-1,3,5(10)-trien-17-on

13β-ethyl-18,19-dinor-17α-pregna-1,3,5(10)-trien-20-yne-3,17β-diol

dl-13-ethyl-3-methoxygona-1,3,5⁽¹⁰⁾-trien-17-one

l-3-Benzyloxy-13β-ethylgona-1,3,5(10)-trien-17β-ol

Refernces

• 1、 Ali,Rousseau,Lafreniere,van Lier. "(17alpha,20E/Z)-iodovinyl- and 16alpha-iodP618-homoestradiol derivatives: synthesis and evaluation for estrogen receptor imaging.". . p. 74 - 84. Retrieved 2007/10/03.
• 2、 Rufer,Schr?der,Gibian. "Total synthesis of optically active steroids. 7. Synthesis and properties of modified estratriene derivatives". . p. 1 - 13. Retrieved 2007/10/11.