13260-75-8

Usage

InChI:InChI=1/C8H14O2/c1-4-7-9-5-8(2,3)6-10-7/h4,7H,1,5-6H2,2-3H3

Upstream product

• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 107-02-8 acrolein 

Downstream Products

• 117919-20-7 2,2-Dimethyl-3-((1E,5E)-6-phenyl-hexa-1,5-dienyloxy)-propan-1-ol 
• 117919-06-9 5,5-Dimethyl-2-((E)-1-methyl-4-phenyl-but-3-enyl)-[1,3]dioxane 
• 1133389-57-7 C₁₅H₂₂O₃ 
• 58697-03-3 3-(5,5-dimethyl-1,3-dioxanyl)-propionaldehyde 
• 136831-03-3 5,5-dimethyl-2-ethynyl-1,3-dioxane 
• 117919-38-7 2-(1-Iodomethyl-2-phenyl-ethyl)-5,5-dimethyl-[1,3]dioxane 
• 117919-18-3 2,2-Dimethyl-3-((E)-4-phenyl-but-1-enyloxy)-propan-1-ol 
• 117919-05-8 5,5-Dimethyl-2-(1-methyl-2-phenyl-ethyl)-[1,3]dioxane 
• 117919-11-6 5,5-Dimethyl-2-((E)-3-phenyl-propenyl)-[1,3]dioxane 

Relevant academic research and scientific papers

Unlocking the Potential of Poly(Ortho Ester)s: A General Catalytic Approach to the Synthesis of Surface-Erodible Materials

Poly(ortho ester)s (POEs) are well-known for their surface-eroding properties and hence present unique opportunities for controlled-release and tissue-engineering applications. Their development and wide-spread investigation has, however, been severely limited by challenging synthetic requirements that incorporate unstable intermediates and are therefore highly irreproducible. Herein, the first catalytic method for the synthesis of POEs using air- and moisture-stable vinyl acetal precursors is presented. The synthesis of a range of POE structures is demonstrated, including those that are extremely difficult to achieve by other synthetic methods. Furthermore, application of this chemistry permits efficient installation of functional groups through ortho ester linkages on an aliphatic polycarbonate.

Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand

A rhodium complex, in conjunction with commercially available Ph-BPE ligand, catalyzes the branch-selective asymmetric hydroformylation of 1-alkenes and rapidly generates α-chiral aldehydes. A wide range of terminal olefins including 1-dodecene were examined, and all delivered high enantioselectivity (up to 98:2 er) as well as good branch:linear ratios (up to 15:1). (Chemical Equation Presented).

Enzymatic transformations 62. Preparative scale synthesis of enantiopure glycidyl acetals using an Aspergillus niger epoxide hydrolase-catalysed kinetic resolution

The hydrolytic kinetic resolution of five glycidaldehyde acetal derivatives was examined using the recombinant Aspergillus niger epoxide hydrolase as biocatalyst. This could successfully be performed, at room temperature, using solely demineralised water as solvent and following a two-phase methodology allowing us to operate at a global substrate concentration as high as 200 g/L in the reactor. The observed E values were shown to be modest to excellent, depending on the structure of the acetal moiety, indicating that it is possible to achieve this resolution very efficiently just by choosing the right substituents. Both the unreacted (R)-epoxide and the formed (S)-diol could thus be obtained in good to excellent ee (ee > 99% for the epoxide). For the best substrates, the reaction could be performed within a few hours by using a biocatalyst over substrate molecular ratio of about 9 to 10 × 10 -4 mol %. The turnover frequency (TOF) as well as the total turnover number (TON) of the enzyme proved to be excellent as compared to chemical catalysts - reaching respectively values in the order of 6 × 10 2 mol sub/mol enz/ min and 6 × 104 mol sub/mol enz. The space-time yield of the best (two-phase) reactor could thus reach a value as high as 56 g/L/hour. As a demonstration experiment, a 50-g scale resolution of glycidaldehyde 2,2-dimethyltrimethylene acetal was performed.

Efficient Synthesis of Acetals Promoted by a Yttria-Zirconia Based Strong Lewis Acid Catalyst

A variety of carbonyl compounds react with 2,2-dimethylpropane-1,3-diol in the presence of a catalytic amount of a novel yttria-zirconia based strong Lewis acid to afford the corresponding acetals in excellent yields.

Preparation and thermal rearrangement of trans-3--2-cyclohexen-1-one. A synthesis of (+/-)-β-himachalene

A total synthesis of the sesquiterpenoid (+/-)-β-himachalene (2) is described.Treatment of 5,5-dimethyl-2-vinyl-1,3-dioxane (24) with bromoform and aqueous sodium hydroxide in the presence of a phase-transfer catalyst afforded the dibromocyclopropane 25.When the latter substance was allowed to react (tetrahydrofuran-hexamethylphosphoramide, -95 deg C) with n-butyllithium in the presence of methyl iodide, a mixture of the epimeric products 26 (87-93percent) and 27 (7-13percent) was produced in high yield.Compound 26 was converted via a two-step sequence (hydrolysis with 88percent formic acid, 26 -> 28; Wittig reaction with isopropylidenetriphenylphosphorane, 28 -> 16) into the bromocyclopropane 16, which was transformed into the cuprate reagent 17.Reaction of 3-iodo-2-cyclohexen-1-one (4) with reagent 17, followed by thermolysis (xylene, reflux) of the resultant product 18 (the title compound), afforded, in quantitative yield, the dione 12.Methylation of 12 furnished compound 29 which, upon hydrogenation in the presence of tris(triphenylphosphine)chlororhodium, gave the ketone 32.Conversion of compound 32 into the corresponding enol phosphate 33, followed by reduction (lithium, ethylamine-tetrahydrofuran, tert-butyl alcohol) of the latter material, provided (+/-)-β-himachalene (2).