31636-92-7

Upstream product

• 29264-40-2 5-pentenylbenzoate 
• 2049-96-9 amyl benzoate 
• 71-41-0 pentan-1-ol 
• 98-88-4 benzoyl chloride 
• 480-91-1 oxisoindole 
• 764-37-4 (E)-3-penten-1-ol 
• 36978-18-4 3-Pentenylbenzoat 
• 128733-39-1 1-benzoyloxy-4-hydroxypentane 
• 126680-65-7 5-((tert-butyldimethylsilyl)oxy)pentan-2-ol 
• 818-56-4 4-methoxypentan-1-ol 
• 86864-59-7 5-((tert-butyldimethylsilyl)oxy)pentan-2-one 
• 96-47-9 2-methyltetrahydrofuran 
• 1071-73-4 5-Hydroxy-2-pentanone 
• 821-09-0 n-Pent-4-enyl alcohol 

Downstream Products

• 128733-39-1 1-benzoyloxy-4-hydroxypentane 
• 1352086-04-4 ethyl 3-(2-ethyl-4-{2-[2-(4-fluorophenyl)-5-methyloxazol-4-yl]ethoxy} phenyl)propionate 
• 196810-30-7 2-[2-(4-fluorophenyl)-5-methyl-1,3-oxazol-4-yl]ethanol 
• 157169-71-6 2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethanol 
• 477541-31-4 2-[2-(4-fluorophenyl)-5-methyloxazol-4-yl]ethyl methanesulfonate 
• 1352085-92-7 3-[2-ethyl-4-(2-{5-methyl-2-[4-(1H-tetrazol-5-yl)phenyl]oxazol-4-yl}ethoxy)phenyl]propanoic acid 
• 1352085-90-5 3-[4-(2-{2-[4-(tert-butyl)phenyl]-5-methyloxazol-4-yl}ethoxy)-2-ethylphenyl]propanoic acid 
• 1352085-93-8 3-(2-ethyl-4-{2-[5-methyl-2-(4-nitrophenyl)oxazol-4-yl]ethoxy}phenyl)propanoic acid 
• 1383439-66-4 C₁₃H₁₃N₅O₂ 
• 1267705-94-1 C₁₂H₁₂N₂O₄ 
• 1383439-60-8 C₂₀H₁₇N₅O₃ 
• 1383439-58-4 C₂₃H₂₅NO₃ 
• 1383439-56-2 C₁₉H₁₆N₂O₅ 
• 1383439-54-0 C₂₀H₁₉NO₃ 

Relevant academic research and scientific papers

N-Ammonium Ylide Mediators for Electrochemical C-H Oxidation

The site-specific oxidation of strong C(sp3)-H bonds is of uncontested utility in organic synthesis. From simplifying access to metabolites and late-stage diversification of lead compounds to truncating retrosynthetic plans, there is a growing need for new reagents and methods for achieving such a transformation in both academic and industrial circles. One main drawback of current chemical reagents is the lack of diversity with regard to structure and reactivity that prevents a combinatorial approach for rapid screening to be employed. In that regard, directed evolution still holds the greatest promise for achieving complex C-H oxidations in a variety of complex settings. Herein we present a rationally designed platform that provides a step toward this challenge using N-ammonium ylides as electrochemically driven oxidants for site-specific, chemoselective C(sp3)-H oxidation. By taking a first-principles approach guided by computation, these new mediators were identified and rapidly expanded into a library using ubiquitous building blocks and trivial synthesis techniques. The ylide-based approach to C-H oxidation exhibits tunable selectivity that is often exclusive to this class of oxidants and can be applied to real-world problems in the agricultural and pharmaceutical sectors.

Erratum: Ruthenium-catalyzed C-H hydroxylation in aqueous acid enables selective functionalization of amine derivatives (Journal of the American Chemical Society (2017) 139:28 (9503-9506) DOI: 10.1021/jacs.7b05469)

Page 9504. The structure of product 3cc in Table 2 was found to be mis-assigned. We thank Prof. Phil Baran and Dr. Rafael Navratil for bringing this error to our attention. The correct structure contains an additional benzylic alcohol at the C-9 position of the steroid (3cc′, shown below). With the accompanying change in molecular weight, the isolated yield is 29%. Supporting Information. The incorrect structure and yield also appeared on pages S20 and S84 in the SI. Given this, the HRMS entry on page S20 should read as follows: “HRMS (ESI-TOF) m/z calcd for C19H18F3O5S+ (M-O+Na)+ 415.0822, found 415.0857”. The complete corrected SI is provided here.

Catalytic Acceptorless Dehydrogenation of Aliphatic Alcohols

We developed the first acceptorless dehydrogenation of aliphatic secondary alcohols to ketones under visible light irradiation at room temperature by devising a ternary hybrid catalyst system comprising a photoredox catalyst, a thiophosphate organocatalyst, and a nickel catalyst. The reaction proceeded through three main steps: hydrogen atom transfer from the α-C-H bond of an alcohol substrate to the thiyl radical of the photo-oxidized organocatalyst, interception of the generated carbon-centered radical with a nickel catalyst, and β-hydride elimination. The reaction proceeded in high yield under mild conditions without producing side products (except H2 gas) from various alcohols, including sterically hindered alcohols, a steroid, and a pharmaceutical derivative. This catalyst system also promoted acceptorless cross-dehydrogenative esterification from aldehydes and alcohols through hemiacetal intermediates.

Regioselective Wacker-Type Oxidation of Internal Olefins in tBuOH Using Oxygen as the Sole Oxidant and tBuONO as the Organic Redox Cocatalyst

A regioselective Wacker-Tsuji oxidation of internal olefins in tBuOH has been developed using oxygen as the terminal oxidant and tert-butyl nitrite as the simple organic redox cocatalyst without the involvement of hazardous cocatalysts or harsh reaction conditions. A series of internal olefins bearing various functional groups can be oxidized to the corresponding substituted ketones in generally good yields with high regioselectivities.

Tuning Regioselectivity of Wacker Oxidation in One Catalytic System: Small Change Makes Big Step

A regioselectivity switchable aerobic Wacker-Tsuji oxidation has been developed using catalytic tert-butyl nitrite as a simple organic redox cocatalyst. By solely switching the solvent, either substituted aldehydes or ketones could be prepared under mild

Branched-selective intermolecular ketone α-alkylation with unactivated alkenes via an enamide directing strategy

We describe a strategy for intermolecular branched-selective α-alkylation of ketones using simple alkenes as the alkylating agents. Enamides derived from isoindolin-1-one provide an excellent directing template for catalytic activation of ketone α-positions. High branched selectivity is obtained for both aliphatic and aromatic alkenes using a cationic iridium catalyst. Preliminary mechanistic study favors an Ir-C migratory insertion pathway.

Ruthenium-Catalyzed C-H Hydroxylation in Aqueous Acid Enables Selective Functionalization of Amine Derivatives

The identification, optimization, and evaluation of a new catalytic protocol for sp3 C-H hydroxylation is described. Reactions are performed in aqueous acid using a bis(bipyridine)Ru catalyst to enable oxidation of substrates possessing basic amine functional groups. Tertiary and benzylic C-H hydroxylation is strongly favored over N-oxidation for numerous amine derivatives. With terpene-derived substrates, similar trends in reactivity toward tertiary and benzylic C-H bonds are observed. Hydroxylation of chiral tertiary centers is enantiospecific in spite of the ionizing strength of the reaction medium. Preliminary kinetics experiments show a marked difference in reactivity between isomeric cis- and trans-Ru catalysts suggesting that the catalyst is configurationally stable under the reaction conditions.

Oxidation of Secondary Methyl Ethers to Ketones

We present a mild way of converting secondary methyl ethers into ketones using calcium hypochlorite in aqueous acetonitrile with acetic acid as activator. The reaction is compatible with various oxygen- and nitrogen-containing functional groups and afforded the corresponding ketones in up to 98% yield. The use of this methodology could expand the application of the methyl group as a useful protecting group.

Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non-UV-Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method

Property tuning by fluorination is very effective for a number of purposes, and currently increasingly investigated for aliphatic compounds. An important application is lipophilicity (log P) modulation. However, the determination of log P is cumbersome fo

COMPOUNDS HAVING ACTIVATING EFFECT ON SUBTYPES OF PEROXISOME PROLIFERATOR-ACTIVATED RECEPTORS AND ITS PREPARATION METHOD AND USES

Phenyl propanoic acid compounds having activating effect on peroxisome proliferator-activated receptors (PPARα,δ,γ) and a preparation method and uses thereof are provided in the present invention. The compounds can be used for treating or preventing diseases associated with peroxisome proliferator-activated receptors (PPARα,δ,γ).