61808-03-5

Upstream product

• 95-87-4 2,5-Dimethylphenol 
• 75-03-6 ethyl iodide 
• 7647-01-0 hydrogenchloride 
• 109-95-5 ethyl nitrite 
• 64-17-5 ethanol 
• 95-78-3 2,5-Dimethylaniline 
• 132907-18-7 3,6-dimethoxy-3,6-dimethylcyclohexa-1,4-diene 
• 64-67-5 diethyl sulfate 
• 88578-19-2 2,5-dimethyl-benzenediazonium; chloride 

Downstream Products

• 118104-48-6 (4aR,9aS)-7-Ethoxy-5,8-dimethyl-1,2,3,4,4a,9a-hexahydro-fluoren-9-one 
• 290354-22-2 2-ethoxy-α,α'-dibromo-p-xylene 
• 290354-06-2 C₃₀H₅₀N₄O₃ 

Relevant academic research and scientific papers

Heterocyclic amide derivatives

The present invention relates to novel heterocyclic amide derivatives of the formula in which R1, R2, R3 and R4 are as defined in the disclosure, to a process for preparing them, and to their use as pesticides.

New carbamoylpiperidines as human platelet aggregation inhibitors

A series of 3-carbamoylpiperidines (nipecotamides) are designed, synthesized and tested for their inhibitory action against adenosine diphosphate (ADP)-induced aggregation of human platelets. A structure- activity analysis of the bis(nipecotamido)aralkane type showed that a substituent on the piperidine ring should preferably be an amide and that the electronegativity of the carbonyl oxygen and the orientation of the amide group affected activities. Based on the knowledge of factors influencing platelet activation and aggregation, a nitric ester moiety which could release nitric oxide (NO) in situ, is incorporated into the nipecotamide structure. These compounds exhibit increased activity compared to those having no -ONO2 function. They also show stereoselectivity, with the meso isomer being approximately twice as potent as the synthetic diastereomeric mixture. Replacement of the -ONO2 function with hydroxyl, ester or alkyl groups considerably diminishes aggregation-inhibitory potential. Nipecotamides are shown here to inhibit the basal and collagen-induced rise in platelet inositol trisphosphate (IP3) levels, as well as phosphoinositide turnover. A comprehensive mechanism of action is proposed taking earlier results into consideration. (C) 2000 Elsevier Science Ltd.

REACTIVITY OF 3,6-DIMETHOXY-3,6-DIMETHYLCYCLOHEXA-1,4-DIENE: NUCLEAR VERSUS BENZYLIC NUCLEOPHILIC SUBSTITUTION

The treatment of cis/trans-3,6-dimethoxy-3,6-dimethylcyclohexa-1,4-diene (ca. 1/1 mixture; easily prepared electrochemically in multigram scale from p-xylene) under acidic conditions (acetic, trifluoroacetic, sulfuric, or a Lewis acid) yields almost exclusively 2-methoxy-1,4-dimethylbenzene 4, through a trasposition reaction.The use of aqueous hydrochloric or hydrofluoric acid gives 2,5-dimethylphenol 12, and with hydrogen chloride a mixture of 2- and α-chloro-p-xylene (13, 14) is isolated.Different oxygen-, nitrogen-, and sulfur-containing nucleophiles (alcohols,thiols, or hydrazoic acid) react with 3 under acid catalysis giving the corresponding products resulting from a nuclear or/ and benzylic substitution on p-xylene (15 - 20).The reaction of compound 3 with organolithium reagents affords exclusively benzylic products 21 in a regiospecific manner.In all cases the mixtures of isomers are separated by column chromatography.The lithiation of compound 3 with lithium powder or lithium naphthalenide fails, giving p-xylene.A probable mechanism is proposed for the studied reactions.

Phenyl Cations as Reactive Intermediates in the Solvolysis of Dien-in-yl Triflates

The synthesis, separation, and solvolysis of the stereoisomeric 1,4-dimethyl-1,3-hexadien-5-yn-1-yl triflates 15a - c in various solvents are described.In contrast to the (Z)-isomers 15a - c, the (E)-isomers 15a - c react preferably via an intermediate phenyl cation 16 to give the phenyl ethers 17.Further mechanistic investigations which support the formation of the intermediate phenyl cations 16 are described.The formation of the benzylic derivatives 18 is discussed.