38447-06-2

Upstream product

• 42516-28-9 ethyl (2E)-4-(diethoxyphosphoryl)crotonate 
• 100-52-7 benzaldehyde 
• 623-73-4 diazoacetic acid ethyl ester 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 105-36-2 ethyl bromoacetate 
• 535-15-9 ethyl 1,1-dichloroacetate 
• 603-35-0 triphenylphosphine 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 104-54-1 3-Phenylpropenol 
• 17577-28-5 (ethoxycarbonylmethyl)triphenylphosphonium chloride 
• 105-58-8 Diethyl carbonate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 1379820-27-5 C₆H₅CHCHCH(BO₂C₂(CH₃)4)CH₂COOC₂H₅ 
• 38446-98-9 (2E,4Z)-5-phenylpenta-2,4-dienoic acid 
• 1552-94-9 (2Z,4E)-5-phenylpenta-2,4-dienoic acid 
• 102106-95-6 (2Z,4E)-5-phenylpenta-2,4-diene-1-ol 

Relevant academic research and scientific papers

Essential structural features of (2Z,4E)-5-phenylpenta-2,4-dienoic acid for inhibition of root gravitropism

Previously, we found (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) to be a selective inhibitor of root gravitropic bending of lettuce radicles at 5 μM, with no concomitant growth inhibition. Here, we describe a structure-activity relationship study of ku

Carbocation Lewis Acid TrBF4-Catalyzed 1,2-Hydride Migration: Approaches to (Z)-α,β-Unsaturated Esters and α-Branched β-Ketocarbonyls

Carbocation Lewis acid TrBF4-catalyzed 1,2-hydride migration of α-alkyldiazoacetates themselves or in situ-generated cross-coupling adducts of aldehydes and α-alkyldiazoacetates has been developed, affording (Z)-α,β-unsaturated esters and α-branched β-ketocarbonyls, respectively, in good yields and with high regioselectivities.

Cis-cinnamic acid analogue, gravitropism modifier (by machine translation)

[Problem] cinnamic acid or cinnamic acid analogue comprising adjusting agent gravitropism cis. [Solution] cinnamic acid and/or cinnamic acid as an active ingredient to adjust gravitropism cis edge agents, cinnamic acid edge is, for example obtained by reacting compounds of the following formula. (In the formula, R is a phenyl group. )Figure 6 [drawing] (by machine translation)

Facile synthesis of α, β-unsaturated esters through a one-pot copper-catalyzed aerobic oxidation-Wittig reaction

An efficient one-pot synthesis of α, β-unsaturated esters through the aerobic oxidation – Wittig tandem reaction of alcohols and phosphorous ylide is developed. This new method operates under mild reaction conditions, and uses CuI/TEMPO (TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) as co-catalyst and air (O2) as the oxidant. It tolerates a wide range of functionalized benzylic alcohol and aliphatic alcohols.

One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts

A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O 2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO 2 Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.

Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement

A tandem relay catalytic protocol using both Pd and isothiourea catalysis has been developed for the enantioselective synthesis of α-amino acid derivatives containing two stereogenic centers from readily accessible N,N-disubstituted glycine aryl esters and allylic phosphates. The optimized process uses a bench-stable succinimide-based Pd precatalyst (FurCat) to promote Pd-catalyzed allylic ammonium salt generation from the allylic phosphate and the glycine aryl ester. Subsequent in situ enantioselective [2,3]-sigmatropic rearrangement catalyzed by the isothiourea benzotetramisole forms syn-α-amino acid derivatives with high diastereo- and enantioselectivity. This methodology is most effective using 4-nitrophenylglycine esters and tolerates a variety of substituted cinnamic and styrenyl allylic ethyl phosphates. The use of challenging unsymmetrical N-allyl-N-methylglycine esters is also tolerated under the catalytic relay conditions without compromising stereoselectivity.

Highly syn-selective elimination of peterson anti-adducts to give Z-α,β-unsaturated esters

Peterson adducts have been known to stereospecifically give syn-elimination products upon treatment with base except when the product olefin is in conjugation with an electron-withdrawing group. The missing piece has been put in place by using a catalytic amount of DBU, by which syn-elimination could be effected to provide the thermally less stable Z-olefin from the anti-adduct with high selectivity.

Bu 4 N + -Controlled Addition and Olefination with Ethyl 2-(Trimethylsilyl)acetate via Silicon Activation

Catalytic Bu 4 NOAc as silicon activator of ethyl 2-(trimethylsilyl)acetate, in THF, was utilized for the synthesis of β-hydroxy esters, whereas employing catalytic Bu 4 NOTMS gave α,β-unsaturated esters. The established reaction conditions were applicable to a diverse range of aromatic, heteroaromatic, aliphatic aldehydes and ketones. Reactions were achieved at room temperature without taking any of the specialized precautions that are in place for other organometallics. A stepwise olefination pathway via silylated β-hydroxy esters with subsequent elimination to form the α,β-unsaturated ester has been demonstrated. The key to selective product formation lies in use of the weaker acetate activator which suppresses subsequent elimination whereas stronger TMSO - activator (and base) facilitates both addition and elimination steps. The use of tetrabutyl ammonium salts for both acetate and trimethylsilyloxide activators provide enhanced silicon activation when compared to their inorganic cation counterparts.

N-heterocyclic carbene-catalysed Peterson olefination reaction

N-heterocyclic carbenes (NHCs) have been utilised as highly efficient organocatalysts to catalyse Peterson olefination reaction of aldehydes with trimethylsilylketene ethyl trimethylsilyl acetal or fluoro(trimethylsilyl)ketene ethyl trimethylsilyl acetal to produce the corresponding functionalized olefines in 34-93% yields with excellent stereoselectivities.

Stereoselective Synthesis of 2 Z,4 e -Configured Dienoates through Tethered Ring Closing Metathesis

A two-step sequence leading from racemic allylic alcohols and vinylacetic acid to ethyl (2Z,4E)-dienoates is described. The sequence involves Steglich esterification of the reactants, followed by a one-pot ring closing metathesis-base induced elimination-