107791-76-4

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 5674-01-1 2-methylallylmagnesium chloride 
• 51107-35-8 6-chloro-4,5-epoxy-2-methyl-1-heptene 
• 1458-98-6 2-methyl-3-bromo-1-propene 

Downstream Products

• 21570-35-4 2-methyl-4-heptanol 
• 38142-58-4 (+/-)-ar-turmerone 
• 110774-48-6 5-Methyl-3-methylencyclohexanol 
• 16409-43-1 rose oxide 

Relevant academic research and scientific papers

Asymmetric synthesis of 2°- and 3°-carbinols via B-methallyl-10-(TMS and Ph)-9-borabicyclo[3.3.2]decanes

(Chemical Equation Presented) Simple Grignard procedures provide methallylboranes 1a and 1b in enantiomerically pure form from air-stable precursors in 98% and 95% yields, respectively. These reagents add smoothly to aldehydes and methyl ketones, respecti

Oxidation of substituted 1,5-hexadien-3-ols with various oxidants

Substituted 1,5-hexadien-3-ols were synthesized by the [2,3]-Wittig rearrangement of unsymmetrical bis-allyl ethers, as well as by reactions of 1-(2-alkenyl)-2-chloromethyloxiranes with Mg/THF. The products were oxidized with pyridinium chlorochromate (PCC), zinc chlorochromate (ZCC), tert-butyl hydroperoxide in the presence of OsO4, and tert-butyl hydroperoxide alone. The oxidation of substituted 1,5-hexadien-3-ols with PCC and ZCC gave the corresponding carbonyl compounds. In the reaction with tert-butyl hydroperoxide catalyzed by OsO4 the internal double bond in the substrate was regioselectively converted into epoxy group, whereas allylic oxidation was prevented.

Synthesis of allyl-cyclopropyl alcohols and allyl-1,5-hexadien-3-ols and investigation of their antibacterial and antifungal activities

Two different methods have been used to obtain allyl-cyclopropyl alcohols and allyl-1,5-hexadien-3-ols, starting with various allyl substituted chloromethyloxiranes. While allyl substitued 1,5 - hexadien - 3 - ols are formed in reactions occurring with Mg in THF, the unsaturated cyclic alcohols are also formed. However, the reaction carried out with Na in Ch3OH gives only 1,5-dien-3-ols. Antimicrobial activity of the synthesised compounds has been tested against 16 microorganisms. The compounds have also been screened for their antibacterial and antifungal activities against bacteria, yeasts and moulds.

Use of Hine's D Values To Predict the Position of the Equilibrium in the Cope Rearrangement of Multiply Substituted 1,5-Dienes

A series of 1,5-dienes (1a-f) were employed to test whether Hine's D values can predict the position of equilibrium in Cope rearrangements.In the cases of the substituent pairs , ,, , and , equilibrium constants calculated with Hine's D values gave reasonable agreement with those obtained experimentally.Dienes 1g-i were prepared to test whether reduction of the ?-donating character of a nitrogen substituent (carbamoyl vs dimethylamino) would change the directing ability of the nitrogen group.The aggregate order of directing ability was N(CH3)2 > OCH3 > EtO2CN(CH3) > CH3 > H>.Diene 15a, with a more complicated substitution pattern (OCH3 and CH3 versus CH3 and H) not directly amenable to analysis with D values, can be considered to reduce to the case of .The experimental Keq obtained agreed with that expected for the pair.Dienes 15c and 16b, designed to test the pairs and , respectively, decomposed under the gas phase conditions of the rearrangement.Attempts to effect rearrangement with Pd(II) catalysis failed.

Oxyanion Orientation in Anionic Oxy-Cope Rearrangements

Efficiency of chirality transfer in anionic oxy-Cope rearrangement depends solely on the orientational preference of the oxyanionic bond in the substrates with a single carbinol carbon chiral center.In chairlike transition-state conformations for the rearrangement of simplest substrates like anions generated from (E)-1-phenyl-1,5-hexadien-3-ol and (E)-1,5-heptadien-4-ol, the oxyanionic bond is more prone to adopt the pseudoaxial orientation.On the other hand, anions generated from (E)-2-methyl-1,5-heptadien-4-ol, (E)-5-tert-butyl-1-phenyl-1,5-hexadien-3-ol, and 4-(2'-methyl-1'-cyclohexenyl)-1-buten-3-ol undergo rearrangement via chairlike transition states in which the pseudoequatorial oxyanionic bond is favored.It can thus be surmized that there is a slight stereoelectronic preference for the pseudoaxial oxyanionic bond in the chairlike transition states for the rearrangement of substrates without steric constraints.Substitution at C5 of the basic 1,5-hexadien-3-ol framework of substrates, however, leads to 1,3-diaxial steric interaction in the chairlike transition states with pseudoaxial oxyanionic bond, and pseudoequatorial disposition of oxyanionic bond becomes more favorable.

A ROSE OXIDE SYNTHESIS

A four-step synthesis of rose oxide from crotonaldehyde by Grignard reaction, Claisen rearrangement, reduction, and cyclization, is reported.