55320-58-6

Usage

InChI:InChI=1/C8H16O/c1-8(2,3)6-4-5-7-9/h7H,4-6H2,1-3H3

Upstream product

• 762-62-9 4,4-dimethylpent-1-ene 
• 201230-82-2 carbon monoxide 
• 630-17-1 2,2-dimethylpropyl bromide 
• 33974-41-3 neopentylmagnesium bromide 
• 107442-40-0 (E)-5,5-dimethylhex-2-en-1-ol 
• 762-63-0 cis-4,4-dimethyl-2-pentene 

Relevant academic research and scientific papers

Multicatalytic approach to one-pot stereoselective synthesis of secondary benzylic alcohols

One-pot procedures bear the potential to rapidly build up molecular complexity without isolation and purification of consecutive intermediates. Here, we report multicatalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities (typically >95:5 er) under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Prochiral allylic alcohols can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er, >20:1 dr).

Binuclear Pd(I)-Pd(I) Catalysis Assisted by Iodide Ligands for Selective Hydroformylation of Alkenes and Alkynes

Since its discovery in 1938, hydroformylation has been thoroughly investigated and broadly applied in industry (>107 metric ton yearly). However, the ability to precisely control its regioselectivity with well-established Rh- or Co-catalysts has thus far proven elusive, thereby limiting access to many synthetically valuable aldehydes. Pd-catalysts represent an appealing alternative, yet their use remains sparse due to undesired side-processes. Here, we report a highly selective and exceptionally active catalyst system that is driven by a novel activation strategy and features a unique Pd(I)-Pd(I) mechanism, involving an iodide-assisted binuclear step to release the product. This method enables β-selective hydroformylation of a large range of alkenes and alkynes, including sensitive starting materials. Its utility is demonstrated in the synthesis of antiobesity drug Rimonabant and anti-HIV agent PNU-32945. In a broader context, the new mechanistic understanding enables the development of other carbonylation reactions of high importance to chemical industry.

Discovery and evaluation of nNav1.5 sodium channel blockers with potent cell invasion inhibitory activity in breast cancer cells

Voltage-gated sodium channels (VGSC) are a well-established drug target for anti-epileptic, anti-arrhythmic and pain medications due to their presence and the important roles that they play in excitable cells. Recently, their presence has been recognized in non-excitable cells such as cancer cells and their overexpression has been shown to be associated with metastatic behavior in a variety of human cancers. The neonatal isoform of the VGSC subtype, Nav1.5 (nNav1.5) is overexpressed in the highly aggressive human breast cancer cell line, MDA-MB-231. The activity of nNav1.5 is known to promote the breast cancer cell invasion in vitro and metastasis in vivo, and its expression in primary mammary tumors has been associated with metastasis and patient death. Metastasis development is responsible for the high mortality of breast cancer and currently there is no treatment available to specifically prevent or inhibit breast cancer metastasis. In the present study, a 3D-QSAR model is used to assist the development of low micromolar small molecule VGSC blockers. Using this model, we have designed, synthesized and evaluated five small molecule compounds as blockers of nNav1.5-dependent inward currents in whole-cell patch-clamp experiments in MDA-MB-231 cells. The most active compound identified from these studies blocked sodium currents by 34.9 ± 6.6% at 1 μM. This compound also inhibited the invasion of MDA-MB-231 cells by 30.3 ± 4.5% at 1 μM concentration without affecting the cell viability. The potent small molecule compounds presented here have the potential to be developed as drugs for breast cancer metastasis treatment.

Complete study of the pyrolysis and gasification of scrap tires in a pilot plant reactor

The pyrolysis and gasification of tires was investigated in a pilot plant reactor provided with a system for condensation of semivolatile matter. The study comprised experiments at 450°, 750°, and 1000°C both in nitrogen and 10% oxygen atmospheres. In the gas phase, only methane and benzene yields increased with temperature until 1000°C. In the liquids, the main components were styrene, limonene, and isoprene. The solid fraction (including soot) increased with temperature. Zinc content of the char decreased with increasing temperature. Analysis of the surface area of the solids showed that the area was similar in all cases to that of a commercial carbon black. The higher surface of the soot with respect to the chars was observed. The results coincided with published findings, i.e., kinetic severity function values would produce 0.2% of methane at 450°C and 4.5% at 750°-1000°C.

Asymmetric hydroformylation catalyzed by an Rh( I) -( R,S) -BINAPHOS complex: Substituent effects in olefins on the regioselectivity

Olefins bearing the larger substituants at the allylic position were hydroformylated in the higher iso/normal selectivity when Rh(I)-(R,S)-BINAPHOS was used as a catalyst. Deuterioformylation of 4,4,4-triphenyl-1 -butene suggests that the higher iso/normal ratio may be attributed to the accelerated CO insertion to the iso-alkylrhodium 7i.

Rhodium-catalysed hydroformylation of branched 1-alkenes; bulky phosphite vs. triphenylphosphine as modifying ligand

The influence of alkyl substituents in 1-alkene substrates in the rhodium-catalysed hydroformylation in the presence of tris(2-tertbutyl-4-methylphenyl) phosphite has been studied and compared with that observed for the reaction involving the conventional PPh3-modified catalyst. Hindered alkenes underwent hydroformylation at good rates (i.e. 1300 mol (mol Rh)-1 h-1 for 3,3-dimethyl-1-butene as T = 70°C and P = 20 bar (H2-CO)); under mild conditions the rates were only slightly affected by the alkyl substituents. The selectivity towards the linear aldehyde increases progressively with substitution, from 66% for 1-octene up to 100% for 3,3-dimethyl-1-butene, and the proportion of isomerized alkenes remained substantial (up to 17.4% for allylcyclohexane). The differences between the two systems are explained in terms of the different kinetics observed for them.