17592-40-4

Usage

InChI:InChI=1/C7H13BrO2/c1-4-9-7(6(3)8)10-5-2/h7H,3-5H2,1-2H3

Upstream product

• 10160-86-8 2,3-dibromo-1,1-diethoxypropane 
• 78-10-4 tetraethoxy orthosilicate 
• 14925-39-4 2-bromoacrolein 
• 64-17-5 ethanol 
• 55249-20-2 1,1-dibromo-2-ethoxy-cyclopropane 
• 122-51-0 orthoformic acid triethyl ester 
• 3054-95-3 acrylaldehyde diethyl acetal 

Downstream Products

• 57428-08-7 1-(2-Diethoxymethyl-allyl)-cyclohexene 
• 160012-73-7 methyl 2-(4-ethoxycarbonyl-5-diethoxymethyl-6H-1,3-thiazin-2-yl)-2-methoxy-2-o-methoxycarbonylbenzamidoethanoate 
• 160012-71-5 methyl 2-(4-ethoxycarbonyl-5-diethoxymethyl-4-hydroxy-4H-1,3-thiazin-2-yl)-2-methoxy-2-o-methoxycarbonylbenzamidoethanoate 
• 120476-98-4 (4S,5S)-4-(cyclohexylmethyl)-5-(3',3'-diethoxy-2'-propenyl)oxazolidin-2-one 
• 345627-78-3 [(E)-1-(1-Diethoxymethyl-vinyl)-hepta-4,6-dienyloxymethyl]-benzene 
• 57428-16-7 3-(1-Diethoxymethyl-vinyl)-cyclohexanol 

Relevant academic research and scientific papers

Modular Synthesis of α-Substituted Alkenyl Acetals by a Palladium-Catalyzed Suzuki Reaction of α-Haloalkenyl Acetals with Organoboranes

A modular and straightforward synthetic strategy for the preparation of α-substituted alkenyl acetals has been developed. α-Haloalkenyl acetals react smoothly with (het)aryl boronic acids, aryl boronates, or B-Alkyl-9-borabicyclo[3.3.1]nonanes through Pd-catalyzed Suzuki cross-coupling under mild conditions with good to high yields. This protocol features a broad substrate scope and good functional-group compatibility, and is easily scaled up.

Enantioselective Diels-Alder reaction of α-(acylthio)acroleins: A new entry to sulfur-containing chiral quaternary carbons

A catalytic and enantioselective Diels-Alder reaction of α-(carbamoylthio)acroleins induced by an organoammonium salt of chiral triamine is described. α-(Carbamoylthio)acroleins are designed and synthesized as new sulfur-containing dienophiles for the fir

Formal synthesis of Aspidosperma alkaloids via the intramolecular [3 + 2] cycloaddition of 2-azapentdienyllithiums

A formal synthesis of the Aspidosperma alkaloids aspidospermidine, aspidospermine, and quebrachamine is reported through an efficient preparation of Stork's penultimate intermediate. The key step of the sequence involved an intramolecular [3 + 2] cycloaddition of the 2-azapentadienyllithium 21 formed in situ from the corresponding imine 1, which after N-alkylation of the resulting cycloadduct provided 2 in excellent yield. The synthesis represents a new disconnection of the classical tricyclic ketone used for appendage of the requisite indole.

Synthesis of the 3-methylene-2-vinyltetrahydropyran unit; the hallmark of the sesquiterpene, hodgsonox

(Chemical Equation Presented) The synthesis of some simple compounds containing the previously unreported 3-methylene-2-vinyltetrahydropyran system, a unique feature of the liverwort metabolite, hodgsonoxis reported. Key features are the creation of an ac

1-Bromo-2-ethoxycyclolithium: A Synthetic Equivalent of 2-Lithio or 3-Lithiopropenal. Application to the Synthesis of Juvenile Hormone (JH-II), β-Sinensal, and Jasmonoids.

The ethyl vinyl ether-dibromocarbene adduct was lithiated with butyllithium at -95 deg C in tetrahydrofuran.The resulting lithium carbenoid 3 was allowed to react with various electrophiles to give 1-substituted trans-1-bromo-2-ethoxycyclopropanes (1) in good yields.The trans relationship of Br and OEt groups was found particularly pertinent to the ethanolysis of 1 producing 2-substituted propenal diethyl acetal derivatives.The reaction has been applied to 1-methoxycyclohexene-dibromocarbene adducts, giving rise hereby 2-substituted 2-cyclohepten-1-one dimethyl acetals under ring enlargement.T he transformation has been utilized in the synthesis of a homoterpenoid (JH-II) or a terpenoid (β-sinensal) structure by SN2' substitution of allylic acetates with lithium dimethylcuprate(I) or iron pentacarbonyl respectively.The reaction products of 3 with aldehydes are oxidized with dimethyl sulfoxide to give cyclopropyl ketones whose ethanolysis in the presence of boron trifluoride ether complex gives β-bromo γ-keto aldehyde acetals.Debromination followed by acidic hydrolysis produces γ-keto aldehydes serving as precursors of dihydrojasmone and cis-jasmone.

Synthesis and Reactions of Simple 3(2H)-Furanones

Interest in the total synthesis of natural product antitumor agents which have as a central structural element the 3(2H)-furanone ring system has led to the development of an efficient general synthesis of a variety of simple 3(2H)-furanones.The strategy