20443-62-3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 513-42-8 3-hydroxy-2-methyl-1-propene 

Downstream Products

• 30432-55-4 (2,4-Dimethyl-phenyl)-bis-(2-methyl-allyl)-amine 
• 30432-58-7 Bis-(2-methyl-allyl)-(3-nitro-phenyl)-amine 
• 312329-76-3 N-Formyl-4-methyl-N-(2-methyl-allyl)benzenesulfonamide 
• 1048699-47-3 CH₂C(CH₃)CH₂C₆H₄BO₂C₂(CH₃)4 
• 144783-05-1 2-methyl-N-[(1R)-1-phenylethyl]prop-2-en-1-ylamine 
• 59346-86-0 methyl 3-nitro-4-methallyloxyphenylacetate 
• 113485-00-0 4-(1-Benzenesulfonyl-3-methyl-but-3-enyl)-1-(toluene-4-sulfonyl)-1H-indole 
• 141362-44-9 Benzyl 2(S)-<(tert-butoxycarbonyl)amino>-5-methylhex-5-enoate 
• 30432-57-6 (4-Bromo-phenyl)-bis-(2-methyl-allyl)-amine 
• 30439-02-2 N,N-bis-(2-methylprop-2-enyl)-p-toluidine 
• 22774-82-9 N-methallyl-p-toluidine 

Relevant academic research and scientific papers

Practical and Safe Sulfonylation of 2-Alkynyl and 2-Alkenyl Alcohols Using the Combined Bases of a Catalytic Amount of Tertiary Amine and Potassium Carbonate

Several 2-alkynyl and 2-alkenyl alcohols were effectively sulfonylated with methanesulfonyl chloride or p-toluenesulfonyl chloride using the combined bases of a catalytic amount of tertiary amine and potassium carbonate.The reaction was conducted with reliable safety and while avoiding the disposal of wasted amines.The mesylation of 2-propyn-1-ol proceeded on a large scale (more than 20 kg) without a substantial production of explosive 3-chloro-1-propyne.The choice of the catalysts was important, and sterically unhindered tertiary amines, such as trimethylamine, N,N-d imethylbenzylamine, and triethylamine, were effective.Without these catalysts the reactions were significantly retarded.The reaction was so mild that it could be applied to complex and optically active 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one, which is an important alcohol moiety of synthetic pyrethroids.

Structure guided design of a series of sphingosine kinase (SphK) inhibitors

Sphingosine-1-phosphate (S1P) signaling plays a vital role in mitogenesis, cell migration and angiogenesis. Sphingosine kinases (SphKs) catalyze a key step in sphingomyelin metabolism that leads to the production of S1P. There are two isoforms of SphK and observations made with SphK deficient mice show the two isoforms can compensate for each other's loss. Thus, inhibition of both isoforms is likely required to block SphK dependent angiogenesis. A structure based approach was used to design and synthesize a series of SphK inhibitors resulting in the identification of the first potent inhibitors of both isoforms of human SphK. Additionally, to our knowledge, this series of inhibitors contains the only sufficiently potent inhibitors of murine SphK1 with suitable physico-chemical properties to pharmacologically interrogate the role of SphK1 in rodent models and to reproduce the phenotype of SphK1 (-/-) mice.

Palladium-catalyzed cyclopentenone formation by carbonylative cycloaddition of allylic tosylates and alkynes

Carbonylative cycloaddition of allyl tosylates and alkynes proceeded in the presence of palladium catalysts to afford a range of cyclopentenones. In the presence of methanol, five-component coupling reactions gave methyl cyclopentenyl acetates, whereas in the absence of methanol, (cyclopentenoylmethylidene)furanones were formed from six components. Allyl tosylate was found to be essential for these reactions, as allyl acetate and allyl bromide proved to be ineffective. Georg Thieme Verlag Stuttgart.

Stereoselective synthesis of alcohols. Part LV. Domino hydroformylation-allylboration-hydroformylation reactions to give trans-perhydropyrano[3,2-b] pyridine derivatives

N-Allyl-(E)-γ-aminoallyl boronates 8 and 18, when subjected to hydroformylation conditions, enter into a domino hydroformylation-allylboration-hydroformylation reaction cascade to generate the bicyclic N,O-heterocycles 12 and 20. On reaction of the methal

Practical and efficient methods for sulfonylation of alcohols using Ts(Ms)Cl/Et3N and catalytic Me3N · HCl as combined base: Promising alternative to traditional pyridine

Several alcohols were smoothly and practically tosylated by two methods A and B. Method A uses the TsCl/Et3N (1.5 - 2.5 equiv)/cat. Me3N · HCl (0.1 - 1.0 equiv) reagent. Compared with the traditional Py-solvent method, the method A has merits of its much higher reaction rate, operational simplicity, economy in the use of the amine, and circumvention of the undesirable side reaction from R-OTs to R-CL. Method B uses TsCl/KOH [or Ca(OH)2]/cat. Et3N (0.1 equiv)/cat. Me3N · HCl (0.1 equiv) as the reagent, which will be suited for practical and large scale production for primary alcohols. On both methods A and B, a clear joint action of Et3N and Me3N · HCl catalysts was observed. 1H NMR measurements support the proposed mechanism of the catalytic cycle. Related methanesulfonylation using Et3N and cat. Me3N · HCl in toluene solvent also successfully proceeded, wherein the clear joint action was also observed.

Synthesis of Enantiomerically Pure Unsaturated α-Amino Acids Using Serine-Derived Zinc/Copper Reagents

Treatment of the serine-derived organozinc reagent 2, in benzene/dimethylacetamide, with a THF solution of CuCN*2LiCl gives rise to a zinc/copper reagent 6 which reacts directly with allylic halides and tosylates to give the corresponding enantiomerically pure substitution products 9 in 32-65percent yield (11 examples).The reaction proceeds by formal SN2' displacement of the leaving group.Reaction with propargyl halides gives the corresponding terminal allene 12a.The zinc reagent 2 may also be prepared directly from protected iodoalanine 1 in THF by the Knochel method.Reaction with propargylic tosylates as electrophiles gives rise to the corresponding protected terminal allenic amino acids in 51-81percent yield (four examples); use of enantiomerically enriched propargylic tosylates results in the formation of diastereoisomerically enriched allenic products.Reactions of the zinc/copper reagent 6 with a range of representative electrophiles is explored; use of relatively reactive electrophiles is necessary to obtain satisfactory yields.Finally, the possibility of using the serine-derived iodide 20, in which the carboxylic acid is protected as a methyl ester, is established.This reagent offers advantages over the corresponding benzyl ester protected reagent 6 for the synthesis of unsaturated amino acids.

Lewis-acid Promoted Aromatic Cyclization of &α-Chlorosulfides: Synthesis of Ethyl Isothiochroman-1-carboxylate and Related Compounds

A variety of ethyl isothiochroman-1-carboxylates and related compounds were synthesized by treatment of 2-chloro-2-acetates with stannic chloride in methylene chloride.The same procedure was applied to the synthesis of ethyl 4-chloro-4-methyltetrahydrothiopyran-2-carboxylate.Some isothiochroman-1-carboxylic acids were prepared and evaluated for antiinflammatory activity.Among the compounds tested, 7-phenoxyisothiochroman-1-carboxylic acid showed weak activity.