130-79-0

Usage

Uses

Used in Agricultural Applications:
Diethylstilbestrol Dimethyl Ether is used as an attractant for zoospores in the agricultural industry. The attracted zoospores encyst and then germinate in the presence of DES-Dimethyl Ether, which can be utilized for various purposes such as pest control or studying the life cycle of these organisms.
Used in Research and Development:
In the field of research and development, Diethylstilbestrol Dimethyl Ether serves as a valuable tool for studying the behavior and biology of zoospores. By understanding how these spores respond to the compound, scientists can gain insights into their ecological roles and potential applications in various fields, such as agriculture, biotechnology, and environmental management.

Originator

Dimestrol,Yick-Vic Chemicals

Manufacturing Process

20 g of 1-(1-chlorobutyl)-4-methoxybenzene is dissolved in 50 ml of ether which had been dried over sodium. Separately, 2.8 g of magnesium turnings are covered with 20 ml of ether. 0.2 g of iodine, as a catalyst, is added and the solution of 1-(1-chlorobutyl)-4-methoxybenzene is added at such a rate as to keep the ether refluxing gently. If there action dopes not start immediately after the addition of a few drops of the halide, the solution may be heated cautiously in order to start the reaction. The mixture is then refluxed for another 0.5 hour and then allowed to cool down. During the whole reaction a current of hydrogen or nitrogen is passed through the apparatus. The resulting grignard reagent is filtered, cooled to -10°C and added slowly to a solution of 18 g of 1-(methoxyphenyl)-propan-1-one in 20 ml benzene to which 0.2 g of MnCl2. The grignard reagent is added so slowly that the temperature is kept below 0°C. After 2 hours, the temperature is raised to room temperature and the solvent distilled off in vacuo. The residue is heated to 170°C at a pressure of 0.4 mm Hg. MgCl(OH) is split off and the product distils over. DIETHYLSTILBESTROL DIMETHYL ETHER is dealkylated by heating it for 20 hours with a solution of KOH in glycerin at 190°C in an atmosphere of nitrogen to obtain α,α-diethyl-4,4'-dimethoxystilbene.

Therapeutic Function

Estrogen

Upstream product

• 186581-53-3 diazomethane 
• 71-23-8 propan-1-ol 
• 60-29-7 diethyl ether 
• 56-53-1 diethylstilbestrol 
• 4390-94-7 1,2-bis(4-methoxyphenyl)butanone 
• 925-90-6 ethylmagnesium bromide 
• 32770-68-6 1-(4-methoxy-phenyl)-propan-1-one-hydrazone 
• 5331-23-7 3,4-bis-(4-methoxy-phenyl)-hexan-3-ol 
• 856348-33-9 3-(4-methoxy-phenyl)-hexane-3,4-diol 
• 53530-36-2 (Z)-3,4-bis(4-methoxyphenyl)hex-2-ene 
• 53530-36-2 (E)-3,4-bis(4-methoxyphenyl)hex-2-ene 
• 109-63-7 trifluoroborane diethyl ether 
• 760-02-1 2-ethyl-1-nitro-2-butene 
• 100-66-3 methoxybenzene 

Downstream Products

• 56-53-1 diethylstilbestrol 
• 18839-90-2 (E)-4-[1-ethyl-2-(4-methoxyphenyl)-1-butenyl]-phenol 
• 130-78-9 racem.-3,4-bis-(4-methoxy-phenyl)-hexane 
• 873415-24-8 3,4-dibromo-3,4-bis-(4-methoxy-phenyl)-hexane 
• 57660-12-5 trans-1,1-dichloro-2,3-diehyl-2,3-bis(4-methoxyphenyl)-cyclopropane 
• 5789-37-7 trans-2,3-diethyl-2,3-bis(4-methoxyphenyl)oxirane 
• 130-78-9 meso-3,4-Bis(4-methoxyphenyl)hexan 
• 28231-25-6 meso-hexestrol dimethyl ether 
• 121-97-1 4-Methoxypropiophenone 
• 57660-16-9 trans-1,2-diethyl-1,2-bis-(4-methoxyphenyl)cyclopropane 
• 84608-97-9 trans-<4,4'-(1,2-diethyl-1,2-cyclopropanediyl) bis (phenyl)>-diacetate 
• 57660-13-6 trans-<4,4'-(3,3-dichloro-1,2-diehyl-1,2-cyclopropanediyl) bis (phenyl)>-diacetate 
• 115-42-4 4,4-bis-(4-methoxy-phenyl)-hexan-3-one 
• 59971-19-6 (E)-2,2'-((hex-3-ene-3,4-diylbis(4,1-phenylene))bis(oxy))diethanol 

Relevant academic research and scientific papers

Stereoselective formation of 1,2-diiodoalkenes and their application in the stereoselective synthesis of highly functionalised alkenes via Suzuki and Stille coupling reactions

Treatment of an alkyne with iodine monochloride and sodium iodide at room temperature results in the formation of the thermodynamic (E)-diiodoalkene. The corresponding (Z)-diiodoalkene can also be produced, by treatment of the alkyne with iodine monochloride at -78 °C in the presence of tetraethylammonium iodide. Such 1,2-diiodoalkenes are useful for the synthesis of more functionalised alkenes by using either Stille or Suzuki cross-coupling protocols. The Royal Society of Chemistry 2000.

InCl3-Zn. A novel reduction system for the deoxygenative coupling of carbonyl compounds to olefins

A simple and inexpensive procedure for the deoxygenative homo-coupling and cross-coupling of carbonyl compounds with InCl3-Zn system in dry acetonitrile at ambient pressure is achieved. The procedure gives excellent yields of E-olefinic products.

Optically Active trans-Diethylstilbesterol Oxide Monomethyl Ether

Diethylstilbestrol oxide is a metabolic intermediate of diethylstilbestrol.In order to elucidate the effects of optically active diethylstilbestrol oxides on microtubule assembly and cell culture, we synthesized (+/-)-diethylstilbestrol oxide (2a).Since 2a was not stable under moderately acidic and basic conditions, the monomethyl ether (2c) of diethylstilbestrol oxide, which was more stable than 2a, was separated by high-pressure liquid chromatography using a chiral column.The mono (4-bromobenzoate) of (-)-2c was analyzed by X-ray crystallography and its absolute structure was determined as C (1R,1'R).Keywords: optical resolution; diethylstilbestrol oxide monomethyl ether; absolute structure; X-ray crystallography; pig liver esterase; diethylstilbestrol oxide

Stereochemistry and Side Products in Reductive Coupling of Alkyl Aryl Ketones to 1,2-Dialkyl-1,2-diarylethylenes

The reductive coupling of alkyl aryl ketones 1 - 3 and 7 - 9 by low valent titanium salts yields predominantly the (Z)-isomers of 11 - 13 and 17 - 19.Evidence is given by 1H NMR spectroscopy.This behavior can be explained by ?-complex formation of phenyl rings with Ti0.Severe steric hindrance, however, favors the (E)-isomers ( -> 14 and 15).Donor groups in p-position, particularly, give increasing amounts of pinacols, 23 - 27, which undergo rearrangement to the ketones 28 and 29.