1507-88-6

Upstream product

• 1504-55-8 2-methyl-3-phenylprop-2-en-1-ol 
• 103729-80-2 2-methyl-1-phenylprop-2-en-1-ol 
• 101-39-3 2-methyl-3-phenyl-2-propenal 
• 7042-33-3 ethyl (E)-2-methyl-3-phenyl-2-propenoate 
• 1504-55-8 (E)-3-phenyl-2-methyl-2-propenol 
• 1895-97-2 2-methyl-3-phenylacrylic acid 
• 100-52-7 benzaldehyde 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 

Downstream Products

• 1504-55-8 2-methyl-3-phenylprop-2-en-1-ol 
• 97294-41-2 <(E)-2-methyl-3-phenyl-2-propenyl>hydrazine 
• 103729-80-2 2-methyl-1-phenylprop-2-en-1-ol 
• 30649-19-5 (E)-2-methyl-1-phenyl-1-pentene 
• 60428-21-9 (E)-(2-methylhex-1-enyl)benzene 
• 88333-74-8 2-<<(E)-2-methyl-3-phenyl-2-propenyl>hydrazono>propionic acid 
• 123762-55-0 C₁₂H₁₆ 

Relevant academic research and scientific papers

Photoenzymatic Synthesis of α-Tertiary Amines by Engineered Flavin-Dependent "ene"-Reductases

α-Tertiary amines are a common motif in pharmaceutically important molecules but are challenging to prepare using asymmetric catalysis. Here, we demonstrate engineered flavin-dependent ‘ene'-reductases (EREDs) can catalyze radical additions into oximes to prepare this motif. Two different EREDs were evolved into competent catalysts for this transformation with high levels of stereoselectivity. Mechanistic studies indicate that the oxime contributes to the enzyme templated charge-transfer complex formed between the substrate and cofactor. These products can be further derivatized to prepare a variety of motifs, highlighting the versatility of ERED photoenzymatic catalysis for organic synthesis.

Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal

Herein, we report a Cu-catalyzed enantioselective allylic alkylation using a γ-butyrolactone-derived silyl ketene acetal. Critical to the development of this work was the identification of a novel mono-picolinamide ligand with the appropriate steric and electronic properties to afford the desired products in high yield (up to 96 %) and high ee (up to 95 %). Aryl, aliphatic, and unsubstituted allylic chlorides bearing a broad range of functionality are well-tolerated. Spectroscopic studies reveal that a CuI species is likely the active catalyst, and DFT calculations suggest ligand sterics play an important role in determining Cu coordination and thus catalyst geometry.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

Substrate structural effects in yttrium(III)-catalyzed hydroamination/ cyclizations of 1,2-disubstituted and 1,1,2-trisubstituted aminoalkenes terminated by 2-(phenyl) and 2-(2-heteroarenyl) groups

A series of 2-phenyl- and 2-(2-heteroarenyl)-bearing amines possessing 1,2-disubstituted and 1,1,2-trisubststuted alkenes have been evaluated in intramolecular hydroaminations catalyzed by Y[N(TMS)(1. Aminoalkenes possessing a terminal 2-(5-trimethylsilyl)thienyl group exhibited substantially enhanced reactivity compared to their 2-(phenyl)-containing counterparts. Cyclization efficiencies imparted by the 2-[(5-trimethylsilyl)furanyl] substituent were comparable or only slightly better than those obtained with the simple the 2-(phenyl) group. Georg Thieme Verlag Stuttgart · New York.

Controlling 6-endo-selectivity in oxidation/bromocyclization cascades for synthesis of aplysiapyranoids and other 2,2,6,6-substituted tetrahydropyrans

A cascade, composed of (i) oxovanadium(V)-catalyzed oxidation of bromide by tert-butyl hydroperoxide and (ii) stereoselective 6-endo-bromocyclization, affords 3-bromo-2-aryl-2,6,6-trimethyltetrahydropyrans from styrene-type tertiary alkenols in synthetically useful yields. (E)-Alkenols add the bromo- and the alkoxy substituent anti-selectively across the double bond, indicating a bromonium ion-mechanism for the ring closure. 6-endo-control of the alkenol cyclization thereby arises from the polar effect of the aryl substituent. Two methyl substituents bound to the alkene terminus are not similarly able to favor 6-endo-cyclization, because strain arising from methyl group repulsion, as the bromonium-activated π-bond and the hydroxyl oxygen approach, directs bromocyclization of tertiary prenyl-type substrates toward tetrahydrofuran formation. A hexasubstituted bromotetrahydropyran prepared from the oxidation/bromocyclization cascade served as starting material for synthesis of racemic aplysiapyranoid A, in a sequence of free radical and polar functional group interconversion.

INHIBITION AND DISPERSION OF BACTERIAL BIOFILMS WITH IMIDAZOLE-TRIAZOLE DERIVATIVES

Disclosure is provided for imidazole-triazole derivative compounds that prevent, remove and/or inhibit the formation of biofilms, compositions comprising these compounds, devices comprising these compounds, and methods of using the same.

Carboazidation of chiral allylsilanes: Experimental and theoretical investigations

The carboazidation of chiral allylsilanes has been investigated by varying the nature of the substituents at the silicon center and on the carbon framework. The influence of temperature and the nature of the sulfonyl azide, as well as the stereochemistry of the remote stereogenic center, on the 1,2-diastereocontrol of the process were considered. Good to excellent levels of diastereocontrol were generally observed, with the syn-β-azidosilane always being formed as the major isomer. An illustration of the value of this methodology has been provided with a short and efficient synthesis of an analogue of castanospermine. EPR spectroscopy was carried out on various β-silyl radicals providing useful information about their conformations in the ground state. Based on this experimental evidence and DFT calculations, reactant-like transition state models were finally proposed that rationalize the observed 1,2-stereoinduction.

β-disubstituted allylic chlorides: Substrates for the Cu-catalyzed asymmetric SN2′ reaction

Scope broadened: A previously developed asymmetric Cu-catalyzed allylic substitution can be applied to more substituted allylic patterns. Two classes of β-disubstituted substrates, cinnamyl derivatives and aliphatic endocyclic allylic chlorides, afford excellent regio- and enantioselectivities (see schemes; L* = phosphoramidite ligand). (Chemical Equation Presented).

Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven

(Chemical Equation Presented) Antitumor agents (-)-acylfulvene and (-)-irofulven are prepared in an approach that employs the powerful enyne ring-closing metathesis reaction to secure the spiro-bicyclic AB rings. Other key features of this synthesis include an efficient aldol-based introduction of the stereocenter at C2, a diazene-mediated reductive allylic transposition, and a ring-closing metathesis/oxidation sequence.

Access to cyclopropyl cations via carbene fragmentation

Photolysis of cyclopropyloxychlorodiazirines affords cyclopropyloxychlorocarbenes whose fragmentations provide access to ion pairs, which feature cyclopropyl cations.