3461-39-0

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 101, p. 371, 1979 DOI: 10.1021/ja00496a016Tetrahedron Letters, 27, p. 3107, 1986 DOI: 10.1016/S0040-4039(00)84727-9

InChI:InChI=1/C11H14O2/c1-9(8-11(12)13-2)10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3

Upstream product

• 15681-48-8 lithium dimethylcuprate 
• 103-26-4 Methyl cinnamate 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 67-56-1 methanol 
• 769-59-5 3-phenyl-butan-2-one 
• 96013-61-5 4,N-Dimethyl-N-(3-phenyl-butyryl)-benzenesulfonamide 
• 623-43-8 crotonic acid methyl ester 
• 3461-38-9 3-methylenebenzenepropanoic acid methyl ester 
• 917-54-4 methyllithium 
• 75-16-1 methylmagnesium bromide 
• 103-26-4 methyl cinnamate 
• 1184-53-8 methylcopper 
• 56955-37-4 1-Methoxy-2-methyl-2-phenylcyclopropanol 
• 98-83-9 isopropenylbenzene 

Downstream Products

• 2031-46-1 (R)-3-phenylbutanol 
• 2031-46-1 (3S)-3-phenylbutan-1-ol 
• 71686-93-6 3-oxo-2-(1-phenyl-ethyl)-butyric acid methyl ester 
• 1328497-73-9 3-phenyl-N-(quinolin-8-yl)butanamide 
• 51552-98-8 3-phenylbutanoyl chloride 
• 6072-57-7 3-methylindanone 
• 1441-20-9 (R)-(-)-3-phenylbutyric acid methyl ester 
• 221878-55-3 (R)-(-)-vinyl 3-phenylbutanoate 
• 772-14-5 (R)-3-phenylbutyric acid 
• 280743-71-7 (+)-benzyl 3-phenylbutanoate 
• 1472-07-7 methyl (R)-3-phenylbutanoate 
• 54541-41-2 methyl 2-methyl-3-phenylbutanoate 

Relevant academic research and scientific papers

From 2-thienylcopper couplings to trimethylsilyl-promoted organocopper additions

In this paper we continue a 2-thienylcopper line started about twenty years ago with the cross-coupling with iodobenzenes in quinoline.We now report a preparative and NMR study of the favourable influence of trimethylchlorosilane on the conjugate addition

An umpolung-enabled copper-catalysed regioselective hydroamination approach to α-amino acids

A copper-catalysed regio- and stereoselective hydroamination of acrylates with hydrosilanes and hydroxylamines has been developed to afford the corresponding α-amino acids in good yields. The key to regioselectivity control is the use of hydroxylamine as

Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins

The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.

Asymmetric Umpolung Hydrogenation and Deuteration of Alkenes Catalyzed by Nickel

Nickel-catalyzed asymmetric hydrogenation of several types of alkenes proceeds in high enantioselectivity, using acetic acid or water as the hydrogen source and indium powder as electron donor. The scope of alkenes herein include α,β-unsaturated esters, n

Development of alkyl glycerone phosphate synthase inhibitors: Structure-activity relationship and effects on ether lipids and epithelial-mesenchymal transition in cancer cells

In aggressive tumors, alkylglyceronephosphate synthase (AGPS) controls cellular ether phospholipid utilization and metabolism to promote cancer cell proliferation and motility. SAR studies on the first-in-class AGPS inhibitor 1, discovered by our group, led to the 2,6-difluoro analog 2i which showed higher binding affinity than 1 in vitro. In 231MFP cancer cells, 2i reduced ether lipids levels and cell migration rate. When tested in PC-3 and MDA-MB-231 cancer cells, 2i specifically impaired epithelial to mesenchymal transition (EMT) by modulating E-cadherin, Snail and MMP2 expression levels. Moreover, the combination of siRNAs against AGPS and 2i provided no additive effect, confirming that the modulation of 2i on EMT specifically relies on AGPS inhibition. Finally, this compound also affected cancer cell proliferation especially in MDA-MB-231 cells expressing higher AGPS level, whereas it provided negligible effects on MeT5A, a non-tumorigenic cell line, thus showing cancer specificity.

Iridium-Catalyzed Alkene-Selective Transfer Hydrogenation with 1,4-Dioxane as Hydrogen Donor

The iridium-catalyzed transfer hydrogenation of alkenes using 1,4-dioxane as a hydrogen donor is described. The use of 1,2-bis(dicyclohexylphosphino)ethane (DCyPE), featuring bulky and highly electron-donating properties, led to high catalytic activity. A polystyrene-cross-linking bisphosphine PS-DPPBz produced a reusable heterogeneous catalyst. These homogeneous and heterogeneous protocols achieved chemoselective transfer hydrogenation of alkenes over other potentially reducible functional groups such as carbonyl, nitro, cyano, and imino groups in the same molecule.

Alkoxycarbonylation of olefins with carbon dioxide by a reusable heterobimetallic ruthenium-cobalt catalytic system

The heterobimetallic ruthenium-cobalt catalytic system exhibited good catalytic performance and reusability in the reductive alkoxycarbonylation of olefins with carbon dioxide. Compared to the previous system only consisting of ruthenium catalyst, the binary catalyst system effectively reduced the usage of noble metal and ionic liquid additives. The respective contribution of ruthenium and cobalt catalysts in this multiple-step catalytic process was investigated by a series of condition-controlled experiments. The evolution of the ruthenium catalyst and the occurrence of alkene hydrogenation during the reaction was explained by theortical calculations.

Development of efficient palladium catalysts for alkoxycarbonylation of alkenes

Herein, we report a general and efficient Pd-catalysed alkoxycarbonylation of sterically hindered and demanding olefins including a variety of tri-, tetra-substituted and 1,1-disubstituted alkenes. In the presence of 1,3-bis(tert-butyl(pyridin-2-yl)phosphanyl)propane L3 or 1,4-bis(tert-butyl(pyridin-2-yl)phosphanyl)butane L4 the desired esters are obtained in good yields and selectivities. Similar transformation is obtained using tertiary ether as showcased in the carbonylation of MTBE to the corresponding linear ester in high yield and selectivity.

Palladium-Catalyzed Carbonylation of sec- and tert-Alcohols

A general palladium-catalyzed synthesis of linear esters directly from sec- and tert-alcohols is described. Compared to the classic Koch–Haaf reaction, which leads to branched products, this new transformation gives the corresponding linear esters in high yields and selectivity. Key for this protocol is the use of an advanced palladium catalyst system with L2 (pytbpx) as the ligand. A variety of aliphatic and benzylic alcohols can be directly used and the catalyst efficiency for the benchmark reaction is outstanding (turnover number up to 89 000).

Benzene-based diphosphine ligands for alkoxycarbonylation

The invention relates to benzene-based diphosphine ligands for alkoxycarbonylation. Specifically, the invention relates to compounds of formula (I), where m and n are each independently 0 or 1; R1, R2, R3, R4 are each independently selected from -(C1-C12)-alkyl, -(C3-C12)-cycloalkyl, -(C3-C12)-heterocycloalkyl, -(C6-C20)-aryl, -(C3-C20)-heteroaryl; at least one of the R1, R2, R3, R4 radicals is a -(C3-C20)-heteroaryl radical; and to the use thereof as ligands in alkoxycarbonylation.