40654-82-8

Usage

InChI:InChI=1/C11H14O/c1-10(9-12)7-8-11-5-3-2-4-6-11/h2-6,9-10H,7-8H2,1H3

Upstream product

• 7065-28-3 2-methyl-2-phenethyloxirane 
• 64-18-6 formic acid 
• 92864-70-5 2,3-epoxy-3-methyl-5-phenyl-valeric acid ethyl ester 
• 78-85-3 2-methylpropenal 
• 1694-84-4 tribenzylborane 
• 201230-82-2 carbon monoxide 
• 768-56-9 4-Phenylbut-1-ene 
• 41927-30-4 2-methyl-4-phenylbutan-1-ol 
• 100-39-0 benzyl bromide 
• 10415-88-0 4-phenylbut-2-yl acetate 
• 50-00-0 formaldehyd 
• 100-42-5 styrene 
• 1425046-82-7 2-methyl-N-(2-methyl-4-phenylbutylidene)propan-2-amine 
• 928-55-2 ethyl 1-propenyl ether 

Downstream Products

• 6683-51-8 2-methyl-4-phenyl-1-butene 
• 1234490-12-0 (3S)-3-methyl-5-phenyl-1-pentyne 
• 3023-61-8 (-)-(S)-2-methyl-4-phenylbutan-1-ol 
• 356784-34-4 (2R)-2-methyl-4-phenyl-1-butanol 
• 768-56-9 4-Phenylbut-1-ene 
• 1560-06-1 1-phenyl-2-butene 
• 143097-80-7 2-bromo-4-phenylbutane 
• 73475-33-9 2-methyl-4-phenylbutanenitrile 

Relevant academic research and scientific papers

Method for synthesizing fluorescent dye intermediate aldehyde by hydroformylation of 1,3-diene compound

The invention discloses a method for synthesizing a fluorescent dye intermediate aldehyde by hydroformylation of 1,3-diene compound. The method comprises the following steps: S1, sequentially adding 0.01 mmol (1 mol%) of [Rh(cod)Cl]2, 0.1 mmol of a phosphine ligand(P/Rh=10/1) and 1 mmol of diene into a reaction flask, adding 1 ml of a solvent DMF, putting the reaction flask into a high-pressure reaction kettle, after the reaction is finished, transferring a mixed solution into a 25 mL glass bottle with 200 microliters of n-tridecane as an internal standard by using a rubber head dropper, and detecting; and S2, determining the product yield and the structure through a gas chromatograph and a nuclear magnetic resonance spectrum, wherein the obtained olefin conversion rate is larger than 99%, the aldehyde yield ranges from 61% to 99%, and the regioselectivity of the product aldehyde ranges from 70/30 to 100/0. According to the method disclosed by the invention, the separation and purification steps of aldehyde products are simplified, and the substrate of the dialkene hydroformylation reaction is excellent in universality.

Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines

The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one-pot reductive amination using pyrrolidine as imine-formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups. A DFT study of its mechanism is presented showing that the isomerization takes place via an iridium hydride mechanism with a low energy barrier, in agreement with the mild reaction conditions. (Figure presented.).

Carbonylative Transformation of Allylarenes with CO Surrogates: Tunable Synthesis of 4-Arylbutanoic Acids, 2-Arylbutanoic Acids, and 4-Arylbutanals

In this Communication, procedures for the selective synthesis of 4-arylbutanoic acids, 2-arylbutanoic acids, and 4-arylbutanals from the same allylbenzenes have been developed. With formic acid or TFBen as the CO surrogate, reactions proceed selectively and effectively under carbon monoxide gas-free conditions.

Direct Synthesis of Polysubstituted Aldehydes via Visible-Light Catalysis

Aldehydes are among the most versatile functional groups for synthetic chemistry. However, access to polysubstituted alkyl aldehydes is very limited and requires lengthy synthetic routes that involve multiple-step functional-group conversion. This paper reports a one-step synthesis of polysubstituted aldehydes from readily available olefin substrates using visible-light photoredox catalysis. Despite a number of competing reaction pathways, commercial styrenes react with vinyl ethers selectively in the presence of an acridinium salt photooxidant and a disulfide hydrogen-atom-transfer catalyst under blue LED irradiation. Alkyl aldehydes with different substitution patterns are prepared in good yields. This strategy can be applied to structurally sophisticated substrates.

Cobalt-Catalyzed Silylcarbonylation of Unactivated Secondary Alkyl Tosylates at Low Pressure

A catalytic preparation of silyl enol ethers from unactivated secondary alkyl tosylates is reported. An inexpensive cobalt catalyst is used under mild conditions with low pressures of carbon monoxide. Nucleophilic, anionic cobalt carbonyls facilitate the catalytic activation of a range of alkyl tosylates. The silylcarbonylation offers a practical approach to synthetically valuable silyl enol ethers from simple starting materials.

An air-stable cationic iridium hydride as a highly active and general catalyst for the isomerization of terminal epoxides

We describe the use of an air-stable iridium hydride catalyst for the isomerization of terminal epoxides into aldehydes with perfect regioselectivity. The system operates at low loadings of catalyst (0.5 mol%), is highly practical, scalable, and tolerates functional groups that would not be compatible with Lewis acids typically used in stoichiometric amounts. Evidence for a rare hydride mechanism are provided. This journal is the Partner Organisations 2014.

Tin(IV) chloride promoted reaction of oxiranes with hydrogen peroxide

A group of substituted oxiranes were readily transformed to the corresponding β-hydroxyhydroperoxides (HHP) in good yields in ethereal SnCl4-H2O2 system in which SnCl4 acts as catalyst. Alternatively, treating oxiranes with SnCl4 first, followed by addition of ethereal H2O2 solution achieved primary gem-dihydroperoxides (DHP) in moderate yields. In the case of preparing DHP, SnCl4 first promoted the rearrangement of oxiranes to aldehydes, followed by condensation with hydrogen peroxide to provide DHP as final products. Georg Thieme Verlag Stuttgart · New York.

Isomerization of terminal epoxides by a [Pd-H] catalyst: A combined experimental and theoretical mechanistic study

An unusual palladium hydride complex has been shown to be a competent catalyst in the isomerization of a variety of terminal and internal epoxides. The reaction displayed broad scope and synthetic utility. Experimental and theoretical evidence are provided for an unprecedented hydride mechanism characterized by two distinct enantio-determining steps. These results hold promise for the development of an enantioselective variant of the reaction.

Complementary catalytic strategies to access α-chiral aldehydes

The present article summarizes the development of two novel and complementary catalytic methods to access α-chiral aldehydes. A C1-symmetric chiral (P,N) ligand with a structure derived from the ubiquitous binepine scaffold has been specifically designed for the Pd-catalyzed α arylation of aldehydes to access indane derivatives with a well-defined quaternary stereocenter in high yields and excellent enantioselectivities. In addition, a dinuclear palladium hydride catalyst has been synthesized for the isomerization of terminal and trisubstituted epoxides into aldehydes and ketones respectively. Combined experimental and theoretical investigations pointed to an unprecedented 'epoxide-opening/hydride-transfer' sequence. The mechanism also features two distinct enantio-determining steps in the kinetic resolution of racemic epoxides. Schweizerische Chemische Gesellschaft.

Carbolithiation of styrenes with N-tert-butyl aldimines

The addition of aldimine anions to styrene occurs upon the treatment of N-tert-butyl aldimine with LDA followed by the addition of styrene to give the corresponding aldehyde after hydrolysis. Cyclohexenyl amines are generated when the reactions are performed with unsaturated aldimines. This approach affords 4-phenyl substituted butanals and cyclohexenyl amines in a simple and inexpensive way.