24318-44-3

Upstream product

• 18483-97-1 2-(3-methoxybenzyloxy)tetrahydro-2H-pyran 
• 93-97-0 benzoic acid anhydride 
• 132816-03-6 (3-Methoxy-benzyloxy)-trimethyl-silane 
• 6971-51-3 3-methoxybenzyl alcohol 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 120-46-7 1,3-diphenylpropanedione 
• 100-53-8 phenylmethanethiol 
• 98-86-2 acetophenone 
• 614-16-4 Benzoylacetonitrile 
• 108087-83-8 [(3-methoxyphenyl)methylidene]hydrazine 
• 65864-99-5 1-(diazomethyl)-3-methoxybenzene 

Relevant academic research and scientific papers

Cu(ii)-catalyzed esterification reaction via aerobic oxidative cleavage of C(CO)-C(alkyl) bonds

A novel Cu(ii)-catalyzed aerobic oxidative esterification of simple ketones for the synthesis of esters has been developed with wide functional group tolerance. This process is assumed to go through a tandem sequence consisting of α-oxygenation/esterification/nucleophilic addition/C-C bond cleavage and carbon dioxide is released as the only byproduct.

Catalytic conversion of ketones to esters: Via C(O)-C bond cleavage under transition-metal free conditions

The catalytic conversion of ketones to esters via C(O)-C bond cleavage under transition-metal free conditions is reported. This catalytic process proceeds under solvent-free conditions and offers an easy operational procedure, broad substrate scope with excellent selectivity, and reaction scalability. This journal is

Flow chemistry as a discovery tool to access sp2-sp3 cross-coupling reactions via diazo compounds

The work takes advantage of an important feature of flow chemistry, whereby the generation of a transient species (or reactive intermediate) can be followed by a transfer step into another chemical environment, before the intermediate is reacted with a coupling partner. This concept is successfully applied to achieve a room temperature sp2-sp3 cross coupling of boronic acids with diazo compounds, these latter species being generated from hydrazones under flow conditions using MnO2 as the oxidant.

Copper-catalyzed cross-coupling of thiols, alcohols, and oxygen for the synthesis of esters

Copper-catalyzed, one-pot, three-component coupling reactions using thiols, alcohols, and oxygen to form a variety of esters in good yields were studied. In the presence of easily oxidized benzylic and allylic alcohols, thiols were selectively oxidized to form thionoesters, which underwent facile S/O exchange to afford esters. Thiols may be used as an alternative benzoyl source under mild aerobic conditions.

Cu-catalyzed esterification reaction via aerobic oxygenation and C-C bond cleavage: An approach to α-ketoesters

The Cu-catalyzed novel aerobic oxidative esterification reaction of 1,3-diones for the synthesis of α-ketoesters has been developed. This method combines C-C σ-bond cleavage, dioxygen activation and oxidative C-H bond functionalization, as well as provides a practical, neutral, and mild synthetic approach to α-ketoesters which are important units in many biologically active compounds and useful precursors in a variety of functional group transformations. A plausible radical process is proposed on the basis of mechanistic studies.

Titration of nonstabilized diazoalkane solutions by fluorine NMR

A new protocol for titrating nonstabilized diazoalkane solutions by quantitative 19F NMR is reported. An excess of 2-fluorobenzoic acid dissolved in CDCl3 is treated with the diazoalkane solution at a low temperature, immediately forming the corresponding 2-fluorobenzoate ester upon warming. A significant difference in the 19F chemical shift between the ester and acid is seen, allowing facile and accurate integration to determine titer. The procedure is safe, rapid, and indicates the active diazoalkane concentration with high precision.

5,5′-Dimethyl-3,3′-azoisoxazole as a new heterogeneous azo reagent for esterification of phenols and selective esterification of benzylic alcohols under Mitsunobu conditions

5,5′-Dimethyl-3,3′-azoisoxazole is used as a new efficient heterogeneous azo reagent for the highly selective esterification of primary and secondary benzylic alcohols and phenols with aliphatic and aromatic carboxylic acids via Mitsunobu protocols. The reaction is highly selective for primary benzylic alcohols versus secondary ones, aliphatic alcohols and also phenols. The isoxazole hydrazine byproduct can be simply isolated by filtration and recycled to its azoisoxazole by oxidation.

Inhibitory effects of benzyl benzoate and its derivatives on angiotensin II-induced hypertension

Hypertension is a lifestyle-related disease which often leads to serious conditions such as heart disease and cerebral hemorrhage. Angiotensin II (Ang II) plays an important role in regulating cardiovascular homeostasis. Consequently, antagonists that block the interaction of Ang II with its receptors are thought to be effective in the suppression of hypertension. In this study, we searched for plant compounds that had antagonist-like activity toward Ang II receptors. From among 435 plant samples, we found that EtOH extract from the resin of sweet gum Liquidambar styraciflua strongly inhibited Ang II signaling. We isolated benzyl benzoate and benzyl cinnamate from this extract and found that those compounds inhibited the function of Ang II in a dose-dependent manner without cytotoxicity. An in vivo study showed that benzyl benzoate significantly suppressed Ang II-induced hypertension in mice. In addition, we synthesized more than 40 derivatives of benzyl benzoate and found that the meta-methyl and 3-methylbenzyl 2′-nitrobenzoate derivatives showed about 10-fold higher activity than benzyl benzoate itself. Thus, benzyl benzoate, its derivatives, and benzyl cinnamate may be useful for reducing hypertension.

Efficient and selective conversion of trimethylsilyl and tetrahydropyranyl ethers to their corresponding acetates and benzoates catalyzed by bismuth(III) salts

A variety of TMS and THP ethers are efficiently converted to their corresponding acetates and benzoates with acetic and benzoic anhydrides in the presence of catalytic amounts of Bi(III) salts such as BiCl3, Bi(TFA)3, and Bi(OTf)sub