62266-63-1

Usage

InChI:InChI=1/C9H14O2/c1-7-5-3-4-6-8(7)9(10)11-2/h3-4,7-8H,5-6H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 5406-30-4 6-methyl-cyclohex-3-enecarboxylic acid 
• 623-43-8 methyl crotonate 
• 106-99-0 buta-1,3-diene 
• 186581-53-3 diazomethane 
• 15111-54-3 methyl trans-6-methyl-3-cyclohexene carboxylate 
• 134785-23-2 (+/-)-cis-1-carbomethoxy-2-bromomethyl-4-cyclohexene 
• 5406-30-4 (1RS,6RS)-6-methyl-3-cyclohexene-1-carboxylic acid 
• 2744-05-0 8-oxabicyclo[4.3.0]non-3-en-9-one 
• 80400-46-0 (E,E)-trimethyl(1,3-pentadien-1-yl)silane 
• 292638-85-8 acrylic acid methyl ester 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 

Downstream Products

• 102629-35-6 (1R,6S)-6-Methyl-3-cyclohexene-1-carboxylic Acid 
• 134877-09-1 (+)-cis-1-carbomethoxy-2-methyl-4-cyclohexene 
• 5748-20-9 trimedlure-Y 
• 15111-54-3 (+/-)-cis-1-carbomethoxy-2-methyl-4-cyclohexene 
• 134877-08-0 (-)-cis-1-carbomethoxy-2-methylcyclohexane 
• 5465-09-8 trans-1,2-dimethyl-cyclohexan-4-one 
• 3685-01-6 trans-4,5-dimethylcyclohexene 
• 5259-31-4 (trans-6-methyl-cyclohex-3-enyl)-methanol 

Relevant academic research and scientific papers

Enantioselective Diels-Alder Reactions of Carboxylic Ester Dienophiles Catalysed by Titanium-Based Chiral Lewis Acid

A new titanium-based chiral Lewis acid 1 has been developed using (1R,2R)-1,2-bis-(2-methoxyphenyl)-ethane-1,2-diol as a chiral vicinal diol ligand. This chiral catalyst was found to exhibit uniformly high enantioselectivity towards carboxylic ester dienophiles in Diels-Alder reactions. The chiral vicinal ligand (1R,2R)-1,2-bis-(2-methoxyphenyl)-ethane-1,2-diol is inexpensive and is easily accessible.

Construction of bicyclo[2.2.2]octane ring system via homoallyl-homoallyl radical rearrangement

We designed a sequential three-step, one-pot reaction (homoallyl- homoallyl radical rearrangement reaction) to generate highly functionalized bicyclo[2.2.2]octane ring system, and succeeded in developing a novel synthetic method to bicyclo[2.2.2]octane compounds from simple cyclohexene derivatives.

Enzymes in organic synthesis 49. Resolutions of racemic monocyclic esters with pig liver esterase

Pig liver esterase (PLE)- catalyzed hydrolyses of the racemic methyl esters of cyclobutane-, cyclohexane-, and cyclohex-4-ene-carboxylic acids bearing cis-2-methyl or cis-2-bromomethyl substituents are highly stereoselective, giving the corresponding acid products of ≥ 97% ee. The stereoselectivity of the enzyme exhibits the expected reversal for such compounds, with the absolute configurations of the cyclobutane and cyclohexame acids being of the opposite absolute configuration type, and cyclopentane substrates such as cis-1-carbomethoxy-2-methylcyclopentane representing the change-over structures and giving products of only 22%ee. This stereoselectivtiy reversal, and the absolute configurations preferred, are as predicted by the recently proposed active site model for the enzyme.

The Diels-Alder Route to Allylsilanes from 1-Trimethylsilylbutadienes

The synthesis and Diels-Alder reactions of 1-trimethylsilylbutadiene (3) and its 3-methyl (17), 3-trimethylsilyloxy (20), 4-methyl (4), and 4-trimethylsilyl (6) derivatives are reported.The silyl group reduces somewhat the rate of the Diels-Alder reactions, and has, if anything, a small 'ortho'-directing effect on the regioselectivity in the reactions of (3) with methyl acylate, methyl propiolate, citraconic anhydride, and 2,6-dimethylbenzoquinone.The other substituent in the dienes (17), (20), and (4) is therefore the major influence on the regioselectivity in the reactions of these dienes with methyl acrylate and methyl propiolate.The products of the Diels-Alder reactions of (3), (17), and (4) are allylsilanes, which undergo clean protodesilylation with acid, and, with the acid and ester derived from the maleic anhydride adduct of (3), undergo epoxidation and sulphenylation reactions giving an allyl alcohol (33) and an allyl sulphide (37), respectively.The adducts from (20) can be hydrolysed to β-silylketones, which can be converted into enones by bromination. 1-Pentamethyldisilylbutadiene (15) is no more reactive and no more regioselective than (3).The 'ortho'-adduct (42) from the reaction of (3) and methyl propiolate aromatises with DDQ to give methyl m-trimethylsilylbenzoate (53) in high yield, in a reaction involving rearrangement of the silyl group, even though a direct dehydrogenation is an available pathway.