92585-24-5

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C12H18O/c1-10(9-13)8-11(2)12-6-4-3-5-7-12/h3-7,10-11,13H,8-9H2,1-2H3

Upstream product

• 108-05-4 vinyl acetate 
• 848413-17-2 (2RS,4R)-2-methyl-4-phenylpentan-1-ol 
• 100-42-5 styrene 
• 848413-16-1 (2RS,4S)-2-methyl-4-phenylpentan-1-ol 
• 121266-68-0 (E)-2-methyl-4-phenylpent-2-enal 
• 75-24-1 trimethylaluminum 
• 78330-53-7 (S)-pent-4-en-2-ylbenzene 
• 36617-91-1 (R)-pent-4-en-2-ylbenzene 
• 116724-02-8 (R)-(1-bromopropan-2-yl)benzene 
• 848413-14-9 (2RS,4S)-2-methyl-4-phenylpentanoic acid 
• 848413-15-0 (2RS,4R)-2-methyl-4-phenylpentanoic acid 
• 129315-45-3 (4S*,5R*,6S*,7R*)-3,3,5-Trimethyl-6-<(2,4,6-trimethylphenyl)thio>-7-phenyl-1-octen-4-ol 
• 129315-43-1 (5R*,6S*,7R*)-3,3,5-Trimethyl-6-<(2,4,6-trimethylphenyl)thio>-7-phenyl-1-octen-4-one 
• 129315-46-4 (2R,3S,4R)-2-Methyl-4-phenyl-3-(2,4,6-trimethyl-phenylsulfanyl)-pentanal 

Downstream Products

• 848413-15-0 (2RS,4R)-2-methyl-4-phenylpentanoic acid 

Relevant academic research and scientific papers

Asymmetric Synthesis of Deoxypropionate Derivatives via Catalytic Hydrogenolysis of Enantioenriched Z-Ketene Heterodimers

A diastereoselective approach to deoxypropionate derivatives through Pd/C-catalyzed hydrogenolysis of enantioenriched ketene heterodimers is described. Catalytic hydrogenolysis of the Z-isomer of ketene heterodimers facilitates access to anti-deoxypropion

One-Step Homologation for the Catalytic Asymmetric Synthesis of Deoxypropionates

A one-step homologation protocol for the synthesis of natural products containing deoxypropionate motif is described by the combination of Zr-catalyzed asymmetric carboalumination of alkenes (ZACA)-Pd-catalyzed vinylation and ZACA–oxidation reaction. In contrast to most other synthetic strategies used to date that typically require three steps per deoxypropionate unit due to the functional-group interconversions, our one-step homologation strategy promises to provide a general and more efficient synthetic route toward deoxypropionate natural products as exemplified by significant improvements in the syntheses of intermediates and/or final products of mycolipenic acid 1 and its analogue 2, (?)-rasfonin, and syn- and anti-dicarboxylic acids 5 and 6.

Catalytic Asymmetric Synthesis of Ketene Heterodimer β-Lactones: Scope and Limitations

In this article we describe extensive studies of the catalytic asymmetric heterodimerization of ketenes to give ketene heterodimer β-lactones. The optimal catalytic system was determined to be a cinchona alkaloid derivative (TMS-quinine or Me-quinidine). The desired ketene heterodimer β-lactones were obtained in good to excellent yields (up to 90%), with excellent levels of enantioselectivity (≥90% ee for 33 Z and E isomer examples), good to excellent (Z)-olefin isomer selectivity (≥90:10 for 20 examples), and excellent regioselectivity (only one regioisomer formed). Full details of catalyst development studies, catalyst loading investigations, substrate scope exploration, protocol innovations (including double in situ ketene generation for 7 examples), and an application to a cinnabaramide A intermediate are described. The addition of lithium perchlorate (1-2 equiv) as an additive to the alkaloid catalyst system was found to favor formation of the E isomer of the ketene heterodimer. Ten examples were formed with moderate to excellent (E)-olefin isomer selectivity (74:25 to 97:3) and with excellent enantioselectivity (84-98% ee).

Highly Efficient, Convergent, and Enantioselective Synthesis of Phthioceranic Acid

A new strategy for highly concise, convergent, and enantioselective access to polydeoxypropionates has been developed. ZACA-Pd-catalyzed vinylation was used to prepare smaller deoxypropionate fragments, and then two key sequential Cu-catalyzed stereocontrolled sp3-sp3 cross-coupling reactions allowed convergent assembly of smaller building blocks to build-up long polydeoxypropionate chains with excellent stereoselectivity. We employed this strategy for the synthesis of phthioceranic acid, a key constituent of the cell-wall lipid of Mycobacterium tuberculosis, in just 8 longest linear steps with full stereocontrol. A step-economical synthesis of phthioceranic acid was achieved by using a conceptually new strategy. ZACA-Pd-catalyzed vinylation was used to prepare smaller deoxypropionate building blocks. Then two Cu-catalyzed stereospecific sp3-sp3 cross-couplings linked the smaller fragments together with full inversion of configuration to assemble large polydeoxypropionates in a stereoselective manner. ZACA=Zr-catalyzed asymmetric carboalumination of alkenes.

All-catalytic, efficient, and asymmetric synthesis of α,ω- diheterofunctional reduced polypropionates via "one-pot" Zr-catalyzed asymmetric carboalumination - Pd-catalyzed cross-coupling tandem process

A highly efficient method for the synthesis of stereochemically pure (≥99% ee and >50/1 dr) α,ω-diheterofunctional reduced polypropionates has been developed. The essential features of the method are represented by the conversion of inexpensive styrene in

Chirality and fragrance chemistry: Stereoisomers of the commercial chiral odorants muguesia and pamplefleur

(Chemical Equation Presented) The work describes the enzyme-mediated preparation and the odor evaluation of the single stereoisomers of the commercial odorants Muguesia and Pamplefleur. The synthetic approach to Muguesia stereoisomers helped to clear the assignment of the relative configuration of intermediate diols 5. The odor response of Pamplefleur isomers was found to be rather unusual. No stereoisomer prevailed, but each one played a definite role in establishing the odor sensation of the final blend.

Compounds having protected hydroxy groups

The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.

Beta-ketoester compounds

The beta-ketoesters of formula I are useful as precursors for organoleptic compounds, especially for flavors, fragrances and masking agents and antimicrobial compounds.

Ketone precursors for organoleptic compounds

The invention discloses ketones of formula I: wherein, Y is an optionally substituted alkyl, cycloalkyl, or cycloalkylalkyl, wherein each alkyl group is straight or branched and each alkyl and cycloalkyl group is saturated or unsaturated; R1is hydrogen or a C1-6alkyl group that is substituted, saturated or unsaturated, straight or branched; A is a chromophoric substituted aromatic ring or ring system; n is an integer; and with the proviso that formula I is not 2-ethoxy-1-phenyl-ethanone. These compositions are useful for the delivery of organoleptic compounds, especially of flavors, fragrances, masking agents and antimicrobial compounds.

Stereoselective Additions of Nucleophilic Alkenes to Chiral Thionium Ions

A convenient one-pot process has been developed for conversion of an aldehyde to an arylthionium ion (e.g., Schemes IV and V), which can be trapped by a nucleophilic alkene.The stereochemistry of the reactions of such chiral and prochiral arylthionium ions with achiral and prochiral nucleophilic alkenes has been studied.The major adducts are those predicted by qualitative application of the Cram-Felkin rule.Quantitatively, however, the nature of the thionium aryl group has a marked effect.For example, whereas 12 reacts with the phenylthionium ion derived from 2-phenyl propanol to give keto sulfides 13a and 14a in a ratio of 4:1, the corresponding reaction of the mesitylthionium ion affords the analogous keto sulfides 24a and 25a in a ratio of > 98:2.In reactions between prochiral thionium ions and prochiral enol silanes, good simple (anti) relative stereochemistry is observed, especially with enol silane 35 (Scheme VII, Table IV).Mesitylthionium ions of α-chiral aldehydes react with prochiral enol silanes to give one of the four possible products in predominance (Scheme VIII, Table V).Again, however, enol silane 35 is found to be a superior reagent, giving 41 in 97percent stereoisomeric purity.The α-methyl-β-arylthio ketones produced in these thionium ion reactions can be transformed by a straightforward process, which includes desulfurization, into chain compounds having anti 1,3-dimethyl branches (e.g., Scheme IX).An iterative application of this scheme can be used to prepare deoxypolypropionate structures, as shown in Scheme X.