626-89-1

Usage

InChI:InChI=1/C6H14O/c1-6(2)4-3-5-7/h6-7H,3-5H2,1-2H3

Upstream product

• 75-21-8 oxirane 
• 926-62-5 isobutylmagnesium bromide 
• 2892-94-6 di-iso-butylmagnesium 
• 27720-98-5 isobutylmagnesium iodide 
• 503-30-0 trimethylene oxide 
• 920-39-8 isopropylmagnesium bromide 
• 50-00-0 formaldehyd 
• 4548-78-1 (3-methylbutyl)magnesium bromide 
• 4237-74-5 isoamylmagnesium chloride 
• 59322-58-6 (+/-)-isopropylsuccinic acid diethyl ester 
• 2412-80-8 methyl 4-methylpentanoate 
• 25415-67-2 ethyl isocaproate 
• 1522-34-5 ethyl 2-acetyl-4-methylpentanoate 
• 23850-78-4 4-methyl-1,2-epoxypentane 

Downstream Products

• 848131-14-6 Mono-isohexyl phthalate 
• 6196-80-1 1-iodo-4-methylpentane 
• 691-37-2 4-Methyl-1-pentene 
• 646-07-1 4-Methylpentanoic acid 
• 626-88-0 1-bromo-5-methylpentane 
• 1119-16-0 isocaproic aldehyde 
• 7498-70-6 3.5-Dinitro-benzoesaeure-4-methyl-pentylester 
• 106599-71-7 4-Diethylamino-acetamido-3,5-dimethylphenyl-carbaminsaeure-isohexylester 
• 55527-65-6 (4-Methyl-pentyloxysulfonyl)-phenyl-acetic acid 
• 25552-17-4 5-methyl-1-phenylhexanone 
• 89393-16-8 1-(1-Butoxy-ethoxy)-4-methyl-pentane 
• 87252-96-8 3-Amino-3-phenyl-propionic acid 4-methyl-pentyl ester; hydrochloride 
• 152753-76-9 2-{(E)-2-[Dimethyl-(4-methyl-pentyloxy)-silanyl]-vinyl}-phenol 
• 1003-17-4 2,2-dimethyltetrahydrofuran 

Relevant academic research and scientific papers

Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides

The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.

PNO ligand containing planar chiral ferrocene and application thereof

The invention discloses a PNO ligand containing planar chiral ferrocene and application thereof. The PNO ligand containing planar chiral ferrocene is a planar chiral ferrocene-containing and phenol-containing PNO ligand as shown in a general formula (I) or (II) which is described in the specification, or a planar chiral ferrocene-containing and aryl-phosphoric-acid-containingPNO ligand containing as shown in a general formula (III) or (IV) which is described in the specification, or a planar chiral ferrocene-containing and carbon-chiral-phenol-containingPNO ligand as shown in a general formula (V) or (VI) which is described in the specification. The invention provides tridentate PNO ligands and processes for their complexation with transition metal salts or transition metal complexes; the introduction of salicylaldehyde and derivatives thereof, which are simple and easy to obtain, enables the ligands to have a bifunctionalization effect, and -OH in a formed catalyst has stronger acidity and is beneficial to combination with N/O in polar double bonds. Therefore, due to the bifunctionalization effect of the catalyst, the interaction between the catalyst and a substrate can be greatly improved, so a reaction can obtain higher catalytic activity and stereoselectivity.

Stabilization of NaBH4 in Methanol Using a Catalytic Amount of NaOMe. Reduction of Esters and Lactones at Room Temperature without Solvent-Induced Loss of Hydride

Rapid reaction of NaBH4 with MeOH precludes its use as a solvent for large-scale ester reductions. We have now learned that a catalytic amount of NaOMe (5 mol %) stabilizes NaBH4 solutions in methanol at 25 °C and permits the use of these solutions for the reduction of esters to alcohols. The generality of this reduction method was demonstrated using 22 esters including esters of naturally occurring chiral γ-butyrolactone containing dicarboxylic acids. This method permits the chemoselective reductions of esters in the presence of cyano and nitro groups and the reductive cyclization of a pyrrolidinedione ester to a fused five-membered furo[2,3-b]pyrrole and a (-)-crispine A analogue in high optical and chemical yields. Lactones, aliphatic esters, aromatic esters containing electron-withdrawing groups, and heteroaryl esters are reduced more rapidly than aryl esters containing electron-donating groups. The 11B NMR spectrum of the NaOMe-stabilized NaBH4 solutions showed a minor quartet due to monomethoxyborohydride (NaBH3OMe) that persisted up to 18 h at 25 °C. We postulate that NaBH3OMe is probably the active reducing agent. In support of this hypothesis, the activation barrier for hydride transfer from BH3(OMe)- onto benzoic acid methyl ester was calculated as 18.3 kcal/mol.

Cobalt- and Iron-Catalyzed Isomerization-Hydroboration of Branched Alkenes: Terminal Hydroboration with Pinacolborane and 1,3,2-Diazaborolanes

The synthesis and characterization of a series of structurally varied N-phosphinoamidinate-ligated cobalt complexes is described, along with the successful application of these and a related iron complex as precatalysts in the isomerization-hydroboration of terminal, geminal, and internal alkenes. These reactions proceed under mild conditions (23-65 °C), at relatively low base-metal loadings (1-5 mol %), typically without cosolvent, and with high terminal hydroboration selectivity across a broad spectrum of branched alkenes. With some of the alkene substrates examined, the N-phosphinoamidinate-ligated precatalysts employed herein are shown to provide alternative terminal selectivity versus other previously reported precatalyst classes for such transformations. Reports of terminal-selective metal-catalyzed alkene isomerization-hydroboration disclosed thus far in the literature employ pinacolborane (HBPin); while effective in the system herein, we also report the first examples of such transformations employing either 1,3-dimethyl-1,3-diaza-2-boracyclopentane or benzo-1,3,2-diazaborolane. The application of these 1,3,2-diazaborolanes in place of HBPin in some instances enables novel terminal selectivity in the isomerization-hydroboration of branched alkenes.

Isotope-Labeling Studies Support the Electrophilic Compound i Iron Active Species, FeO3+, for the Carbon-Carbon Bond Cleavage Reaction of the Cholesterol Side-Chain Cleavage Enzyme, Cytochrome P450 11A1

The enzyme cytochrome P450 11A1 cleaves the C20-C22 carbon-carbon bond of cholesterol to form pregnenolone, the first 21-carbon precursor of all steroid hormones. Various reaction mechanisms are possible for the carbon-carbon bond cleavage step of P450 11A1, and most current proposals involve the oxoferryl active species, Compound I (FeO3+). Compound I can either (i) abstract an O-H hydrogen atom or (ii) be attacked by a nucleophilic hydroxy group of its substrate, 20R,22R-dihydroxycholesterol. The mechanism of this carbon-carbon bond cleavage step was tested using 18O-labeled molecular oxygen and purified P450 11A1. P450 11A1 was incubated with 20R,22R-dihydroxycholesterol in the presence of molecular oxygen (18O2), and coupled assays were used to trap the labile 18O atoms in the enzymatic products (i.e., isocaproaldehyde and pregnenolone). The resulting products were derivatized and the 18O content was analyzed by high-resolution mass spectrometry. P450 11A1 showed no incorporation of an 18O atom into either of its carbon-carbon bond cleavage products, pregnenolone and isocaproaldehyde. The positive control experiments established retention of the carbonyl oxygens in the enzymatic products during the trapping and derivatization processes. These results reveal a mechanism involving an electrophilic Compound I species that reacts with nucleophilic hydroxy groups in the 20R,22R-dihydroxycholesterol intermediate of the P450 11A1 reaction to produce the key steroid pregnenolone.

Synthesis of (R)-(-)-muscone from (R)-5-bromo-4-methylpentanoate: A chiron approach

A synthesis of (R)-muscone (1), a valuable musk odorant, is presented. The stereogenic center of muscone was introduced from methyl (R)-5-bromo-4-methylpentanoate (5), a chiral pool molecule developed in our group, and the macrocyclic ring was prepared by ring-closing metathesis (RCM) reaction. Using methyl (R)-5-bromo-4-methylpentanoate, we have accomplished a synthesis of (R)-muscone, a natural macrocyclic musk, based on chiral pool strategy.

Amino acid motifs in natural products: Synthesis of O-acylated derivatives of (2S,3S)-3-hydroxyleucine

(2S,3S)-3-Hydroxyleucine can be found in an increasing number of bioactive natural products. Within the context of our work regarding the total synthesis of muraymycin nucleoside antibiotics, we have developed a synthetic approach towards (2S,3S)-3- hydroxyleucine building blocks. Application of different protecting group patterns led to building blocks suitable for C- or N-terminal derivatization as well as for solid-phase peptide synthesis. With respect to according motifs occurring in natural products, we have converted these building blocks into 3-O-acylated structures. Utilizing an esterification and cross-metathesis protocol, (2S,3S)-3-hydroxyleucine derivatives were synthesized, thus opening up an excellent approach for the synthesis of bioactive natural products and derivatives thereof for structure activity relationship (SAR) studies.

Facile microwave-assisted synthesis of monodispersed ball-like Ag@AgBr photocatalyst with high activity and durability

We reported a rapid one-step microwave-assisted approach to synthesize a plasmonic photocatalyst of ball-like AgBr nanoparticles (ca. 290 nm in average diameter) with a small amount of metal Ag anchored on the surface. The obtained Ag@AgBr nanocomposites were characterized by means of X-ray diffraction, scanning electron microscopy, Transmission electron microscopy, energy dispersive X-ray spectroscopy, X-ray photoelectron spectroscopy and UV-visible diffuse reflectance spectroscopy. The shape, size, and compositions of the Ag@AgBr photocatalysts could be controlled by tuning the microwave irradiation time and the concentrations of polyvinylpyrrolidone (PVP) in the reaction solution. The as-prepared Ag@AgBr plasmonic photocatalysts show excellent visible-light photocatalytic performance and good reusability for decomposing organic pollutant of Rhodamine B (RhB) due to the surface plasmon resonance (SPR) effect of Ag nanoparticles. Meanwhile, the possible degradation pathways of RhB and a mechanism of the plasmonic photocatalytic process were also proposed.

From olefins to alcohols: Efficient and regioselective ruthenium-catalyzed domino hydroformylation/reduction sequence

Exploring the alternatives: Ruthenium imidazoyl phosphine complexes catalyze the domino hydroformylation/reduction of alkenes to alcohols in good yields and with good selectivities (see scheme). Linear aliphatic alcohols are synthesized under reaction conditions typically used in industrial hydroformylations. Copyright

Improved syntheses of high hole mobility phthalocyanines: A case of steric assistance in the cyclo-oligomerisation of phthalonitriles

It has been shown that the base-initiated cyclo-oligomerisation of phthalonitriles is favoured by bulky α-substituents making it possible to obtain the metal-free phthalocyanine directly and in high yield. The phthalocyanine with eight α-isoheptyl substituents gives a high time-of-flight hole mobility of 0.14 cm2·V -1·s-1 within the temperature range of the columnar hexagonal phase, that is 169-189 °C.