4894-61-5

Usage

Uses

Different sources of media describe the Uses of 4894-61-5 differently. You can refer to the following data:
1. Crotyl Chloride is a useful intermediate used in the preparation of crotyltrichlorosilanes and in other crotylsilylation related reactions
2. Crotyl chloride was used in kinetics measurements of reactions of atomic chlorine with series of unsaturated aldehydes and ketones at 298K. (E)Crotyl chloride was also used in the preparation of (E)-crotyltrichlorosilane.

General Description

Crotyl chloride reacts with trichlorosilane in the presence of tertiary amine and copper salt to give the corresponding allyltrichlorosilane.

InChI:InChI=1/C4H7Cl/c1-2-3-4-5/h2-3H,4H2,1H3/b3-2+

Upstream product

• 123-91-1 1,4-dioxane 
• 21890-98-2 (+/-)-chlorocarbonic acid-(1-methyl-allyl ester) 
• 504-61-0 (E)-but-2-enol 
• 598-32-3 2-hydroxy-3-butene 
• 563-52-0 2-chloro-3-butene 
• 124-18-5 decane 
• 4088-60-2 cis-2-buten-1-ol 
• 75-09-2 dichloromethane 
• 142-96-1 dibutyl ether 
• 98-95-3 nitrobenzene 
• 106-99-0 buta-1,3-diene 
• 106-98-9 1-butylene 
• 624-64-6 trans-2-Butene 
• 6117-91-5 (E/Z)-2-buten-1-ol 

Downstream Products

• 111-67-1 2-octene 
• 4894-62-6 3-methylhepta-1,5-diene 
• 4810-09-7 3-methyl-1-heptene 
• 598-32-3 2-hydroxy-3-butene 
• 6117-91-5 (E/Z)-2-buten-1-ol 
• 7688-21-3 cis-2-hexene 
• 4050-45-7 trans-2-hexene 
• 7385-82-2 (E)-5-methyl-2-hexene 
• 4088-54-4 trans-1-methylthio-2-butene 
• 36195-56-9 (E)-but-2-en-1-yl phenyl sulfide 
• 934-10-1 3-phenylbut-1-ene 
• 767-99-7 2-phenylbut-2-ene 
• 504-61-0 (E)-but-2-enol 
• 563-52-0 2-chloro-3-butene 

Relevant academic research and scientific papers

A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols

A study of the deoxyhalogenation of allylic and propargylic alcohols with tetramethyl-α-halo-enamines is reported. Primary allylic and primary and secondary propargylic alcohols gave the corresponding halides in high yields. Secondary allylic and propargylic alcohols yielded the corresponding secondary halides but the reaction also produced some rearranged primary halides (I > Br > Cl). The reactions with tertiary allylic and tertiary propargylic alcohols gave several products and was therefore of little synthetic value. However, the addition of triethylamine to the reaction mixture or the use of lithium alkoxide instead of alcohol brought about a major change of the course of the reaction which led to amides carrying an allyl or an allenyl group at C2. This was shown to result from a Claisen-Eschenmoser rearrangement of an intermediate α-allyloxy- or propargyloxy-enamine.

N - (4 - alkyl - 5 - benzyl thiazole - 2 - yl) amide and its preparation method and application

The invention relates to N-(4-alkyl-5-benzyl thiazole-2-base) enoyl-amine or salt thereof, shown as a chemical structure formula I, wherein in the formula I, R is selected from C1-C2 alkyl, C3-C4 straight chains or C3-C4 branched alkyl; Y1 and Y3 are selected from hydrogen, methyl, ethyl, hydroxyl, methoxyl, ethoxyl, fluorine, chlorine, bromine or iodine; Y2 and Y4 are selected from hydrogen, methyl and ethyl; n is selected from 1,2,3,4,5,6 or 7; z is selected from hydrogen, methyl or phenyl; salt is selected from hydrochloride, hydrobromide, sulphate, phosphate, mesylate, benzene sulfonate and itramine tosylate. The invention provides the application of the N-(4-alkyl-5-benzyl thiazole-2-base) enoyl-amine or the salt thereof in preparation of anticancer drugs.

A mild method for the replacement of a hydroxyl group by halogen. 1. Scope and chemoselectivity

α-Chloro-, bromo- and iodoenamines, which are readily prepared from the corresponding isobutyramides have been found to be excellent reagents for the transformation of a wide variety of alcohols or carboxylic acids into the corresponding halides. Yields are high and conditions are very mild thus allowing for the presence of sensitive functional groups. The reagents can be easily tuned allowing therefore the selective monohalogenation of polyhydroxylated molecules. The scope and chemoselectivity of the reactions have been studied and reaction mechanisms have been proposed.

α-Selective Allylation of Isatin Imines Using Metallic Barium

The Barbier-type allylation of isatin imines with allylic chlorides was achieved by using metallic barium as the promoter. Various α-allylated 3-amino-2-oxindoles were synthesized from the corresponding allylic chlorides and isatin imines. The double-bond geometry of allylic chlorides was retained throughout the reaction. An arylic bromide or iodide functionality of the products was robust to metalation under the optimum reaction conditions.

Catalytic Asymmetric Crotylation of Aldehydes: Application in Total Synthesis of (-)-Elisabethadione

A new, highly efficient Lewis base catalyst for a practical enantio- and diastereoselective crotylation of unsaturated aldehydes with E- and Z-crotyltrichlorosilanes has been developed. The method was employed as a key step in a novel asymmetric synthesis of bioactive serrulatane diterpene (-)-elisabethadione. Other strategic reactions for setting up the stereogenic centers included anionic oxy-Cope rearrangement and cationic cyclization. The synthetic route relies on simple, high yielding reactions and avoids use of protecting groups or chiral auxiliaries.

ISOPRENE OLIGOMER, POLYISOPRENE, PROCESSES FOR PRODUCING THESE MATERIALS, RUBBER COMPOSITION, AND PNEUMATIC TIRE

The invention relates to an isoprene oligomer that contains a trans structural moiety and a cis structural moiety, which can be represented by the following formula (1), wherein at least 1 atom or group in the trans structural moiety is replaced by another atom or group. The invention also relates to a polyisoprene, which is biosynthesized using the isoprene oligomer and isopentenyl diphosphate. Further, this invention provides a rubber composition comprising the isoprene oligomer and/or the polyisoprene, and a pneumatic tire, including tire components (e.g., treads and sidewalls) formed from the rubber composition. wherein n represents an integer from 1 to 10; m represents an integer from 1 to 30; and Y represents a hydroxy group, a formyl group, a carboxy group, an ester group, a carbonyl group, or a group represented by the following formula (2):

Identification of a valuable kinetic process in copper-catalyzed asymmetric allylic alkylation

Copper bottomed: The application of a previously described process of dynamic kinetic asymmetric transformation to acyclic substrates allowed the identification of a relevant kinetic process in the title reaction (see scheme; CuTC= copper(I) thiophencarboxylate, Naphth= naphthyl). The optimization of the reaction conditions and generality of the method, as well as mechanistic considerations are disclosed.

Cross-coupling of aromatic bromides with allylic silanolate salts

The sodium salts of allyldimethylsilanol and 2-butenyldimethylsilanol undergo palladium-catalyzed cross-coupling with a wide variety of aryl bromides to afford allylated and crotylated arenes. The coupling of both silanolates required extensive optimization to deliver the expected products in high yields. The reaction of the allyldimethylsilanolate takes place at 85°C in 1,2-dimethoxyethane with allylpalladium chloride dimer (2.5 mol %) to afford 73-95% yields of the allylation products. Both electron-rich and sterically hindered bromides reacted smoothly, whereas electron-poor bromides cross-coupled in poor yield because of a secondary isomerization to the 1-propenyl isomer (and subsequent polymerization). The 2-butenyldimethylsilanolate (E/Z, 80:20) required additional optimization to maximize the formation of the branched (γ-substitution) product. A remarkable influence of added alkenes (dibenzylideneacetone and norbornadiene) led to good selectivities for electron-rich and electron-poor bromides in 40-83% yields. However, bromides containing coordinating groups (particularly in the ortho position) gave lower, and in one case even reversed, selectivity. Configurationally homogeneous (E)-silanolates gave slightly higher γ-selectivity than the pure (Z)-silanolates. A unified mechanistic picture involving initial γ-transmetalation followed by direct reductive elimination or σ-π isomerization can rationalize all of the observed trends.

One-pot synthesis of heterocyclic compounds initiated by chemoselective addition to β-acyl substituted unsaturated aldehydes with nucleophilic tin complexes

β-Acyl substituted unsaturated aldehydes 1 were revealed to be good precursors for the synthesis of various heterocyclic compounds by the combination with tin nucleophiles. Various 2-monosubstituted pyrroles were prepared in an one-pot procedure via the reductive amination of formyl groups of 1 by using Bu2SnIH-HMPA complex. One-pot synthesis of heterocycles was carried out initiated by chemoselective reduction of 1 with Bu3SnH-HMPA complex and the subsequent reaction with heterocumulenes. Furthermore, the one-pot synthesis of nitrogen heterocyclic compounds accompanying chemo-, regio- and diastereoselective carbon-carbon bond formation in side chain moieties was effectively accomplished initiated by the regio- and diastereoselective allylation of the formyl group of 1 with allylic tin species.

Asymmetric, anti-selective scandium-catalyzed Sakurai additions to glyoxyamide. Applications to the syntheses of N-Boc D-alloisoleucine and D-isoleucine

An enantio- and diastereoselective Sakurai-Hosomi reaction, catalyzed by chiral scandium pyridyl-bis(oxazoline) (pybox) complexes, has been developed. Both alkyl- and aryl-substituted allylsilanes are effective coupling partners with N-phenylglyoxamide. Applications of this reaction to the asymmetric syntheses of N-Boc D-alloisoleucine and D-isoleucine are described.