64245-70-1

Upstream product

• 64245-64-3 (Z)-5-Methoxy-3-methyl-5-phenyl-pent-2-enal 
• 1222538-53-5 3-methylene-5,5-diethoxy-1-phenylpentan-1-ol 
• 1222538-62-6 4-methylidene-6-phenyl-2-ethoxytetrahydro-2H-pyran 
• 78108-48-2 2-lithio-1-trimethylsiloxyethylene 
• 1896-62-4 (E)-benzalacetone 
• 586354-79-2 ethyl 3-methyl-5-phenylpenta-2,4-dienoate 
• 123-73-9 trans-Crotonaldehyde 
• 42599-24-6 E-styryl iodide 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 57132-28-2 (E)-2-methyl-4-phenylbut-3-en-2-ol 
• 68-12-2 N,N-dimethyl-formamide 
• 100-52-7 benzaldehyde 
• 52062-24-5 (E)-1-acetoxy-3-methyl-1,3-butadiene 
• 122342-11-4 bromo-4 methyl-3 trimethylsiloxy-1 butadiene 

Downstream Products

• 53701-48-7 (2E,4E)-3-methyl-5-phenylpenta-2,4-dienal 
• 20430-09-5 (2Z,4E)-3-methyl-5-phenylpenta-2,4-dienoic acid 
• 1377848-03-7 (R,E)-6-phenyl-4-styryl-6-(trifluoromethyl)-5,6-dihydro-2H-pyran-2-one 
• 942416-34-4 (S)-(-)-3-methyl-5-phenylpentanaldehyde 
• 41927-33-7 (S)-(-)-3-methyl-5-phenylpentan-1-ol 
• 1537904-32-7 (3R,5S)-3,5-diphenyl-7-((E)-styryl)-2,3,5,6-tetrahydropyrazolo[1,2-a][1,2]diazepine-1,9-dione 
• 1003580-04-8 3-methyl-5-phenyl-2,4-pentadienoic acid 

Relevant academic research and scientific papers

Synthesis of phenyl analog of retinoic acid methyl ester proceeding from 3-(bromomethyl)but-3-enal diethylacetal

Aromatic analog of retinoic acid methyl ester was prepared using a convenient prenylating agent, 3-(bromomethyl)but-3-enal diethylacetal, and Barbier reaction in the key stage of building up the carbon chain of target molecules. A version is offered of the synthesis of methylidene analog of aromatic retinoic acid.

STERO CONTROLLED SYNTHESIS OF (E,Z)-DIENALS VIA TANDEM RH(I) CATALYZED PROPARGYL CLAISEN REARRANGEMENT

A novel Rh(I)-catalyzed approach to synthesizing functionalized (E,Z) dienal compounds has been developed via tandem transformation where a stereoselective hydrogen transfer follows a propargyl Claisen rearrangement. Z-Stereochemistry of the first double

Rh(I)-catalyzed transformation of propargyl vinyl ethers into (E, Z)-dienals: Stereoelectronic role of trans effect in a metal-mediated pericyclic process and a shift from homogeneous to heterogeneous catalysis during a one-pot reaction

The combination of experiments and computations reveals unusual features of stereoselective Rh(I)-catalyzed transformation of propargyl vinyl ethers into (E,Z)-dienals. The first step, the conversion of propargyl vinyl ethers into allene aldehydes, proceeds under homogeneous conditions via a cyclization-mediated mechanism initiated by Rh(I) coordination at the alkyne. This path agrees well with the small experimental effects of substituents on the carbinol carbon. The key feature revealed by the computational study is the stereoelectronic effect of the ligand arrangement at the catalytic center. The rearrangement barriers significantly decrease due to the greater transfer of electron density from the catalytic metal center to the CO ligand oriented trans to the alkyne. This effect increases electrophilicity of the metal and lowers the calculated barriers by 9.0 kcal/mol. Subsequent evolution of the catalyst leads to the in situ formation of Rh(I) nanoclusters that catalyze stereoselective tautomerization. The intermediacy of heterogeneous catalysis by nanoclusters was confirmed by mercury poisoning, temperature-dependent sigmoidal kinetic curves, and dynamic light scattering. The combination of experiments and computations suggests that the initially formed allene-aldehyde product assists in the transformation of a homogeneous catalyst (or a cocktail of catalysts) into nanoclusters, which in turn catalyze and control the stereochemistry of subsequent transformations.

Peptide-catalyzed regio- and enantioselective reduction of α,β,γ,δ-unsaturated aldehydes

A resin-supported peptide catalyst (see box in the scheme) was used in the title reaction. The inherent regioselectivity was overcome by the peptide catalyst to promote the 1,6-selective reaction prior to 1,4-reduction. High stereoconvergence was also achieved when using a mixture of geometric isomers of the starting aldehydes. Ach=1-amino-1-cyclohexanecarboxylic acid. Copyright

Stereocontrolled synthesis of (E,Z)-dienals via tandem Rh(I)-catalyzed rearrangement of propargyl vinyl ethers

A novel Rh(I)-catalyzed approach to functionalized (E,Z) dienals has been developed via tandem transformation where a stereoselective hydrogen transfer follows a propargyl Claisen rearrangement. Z-Stereochemistry of the first double bond suggests the involvement of a six-membered cyclic intermediate whereas the E-stereochemistry of the second double bond stems from the subsequent protodemetalation step giving an (E,Z)-dienal.

Oxidative γ-addition of enals to trifluoromethyl ketones: Enantioselectivity control via lewis acid/n-heterocyclic carbene cooperative catalysis

An oxidative γ-functionalization of enals under N-heterocyclic carbene (NHC) catalysis to give unsaturated δ-lactones is disclosed. Enantioselectivity control involving the relatively remote enal γ-carbon was achieved via Lewis acid [Sc(OTf)3 or combined Sc(OTf) 3/Mg(OTf)2] and NHC cooperative catalysis.

Preparation of 3-bromomethyl-3-butenal diethylacetal and its conversion into isoprenoid aldehydes derivatives

The cyclopropanation of ethyl 3,3-diethoxypropionate with alkoxytitanacyclopropane reagents followed by the cleavage of the three-membered carbocycle in the formed cyclopropyl mesylate provided in a good yield 3-bromomethyl-3-butenal diethylacetal. The la

Heck reactions of crotonaldehyde

A direct method for the synthesis of β,β-disubstituted-α, β-unsaturated aldehydes via Heck reaction of aryl halides with crotonaldehyde and related substrates has been developed. The reaction provides rapid access to products usually prepared via multistep sequences. The power of the method in combination with an organocatalytic transfer hydrogenation is illustrated with a short asymmetric synthesis of (S)-Florhydral. Georg Thieme Verlag Stuttgart.

HISTONE DEACETYLASE INHIBITORS

Hormone refractory metastatic disease can be treated with an oxyamide-containing compound through the inhibition of HDAC1 or HDAC2.

Obtention of 2,2-(diethoxy) vinyl lithium and 2-methyl-4-ethoxy butadienyl lithium by Arene-catalysed lithiation of the corresponding chloro derivatives. Synthetic applications

Vinylic lithium reagents 1 and 2 could be obtained by the title procedure from their chloro precursors 5 and 6 instead of the less stable corresponding bromo derivatives 3 and 4. Condensation with carbonyl compounds leads to interesting synthetic applications such as a two steps synthesis of retinal 13 from β-cyclocitral 10.