4835-96-5

Usage

InChI:InChI=1/C13H22O2/c1-5-13(14)15-12-8-10(4)6-7-11(12)9(2)3/h5,9-12H,1,6-8H2,2-4H3

Upstream product

• 2216-51-5 (-)-menthol 
• 925-90-6 ethylmagnesium bromide 
• 814-68-6 acryloyl chloride 
• 15356-70-4 menthol 
• 86198-29-0 cyclohexanone oxime acrylate 
• 79-10-7 acrylic acid 
• 108-31-6 maleic anhydride 
• 292638-85-8 acrylic acid methyl ester 
• 89-78-1 menthol 
• 10458-14-7 (2R,5S)-menthone 

Downstream Products

• 128737-35-9 2-(Furan-2-yl-hydroxy-methyl)-acrylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 85238-74-0 3-Phenyl-2-p-tolyl-isoxazolidine-5-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 137441-55-5 C₃₁H₃₈N₂O₃ 
• 137441-51-1 C₂₄H₃₂N₂O₃ 
• 137441-54-4 C₃₁H₃₈N₂O₃S 
• 123522-48-5 1-Methyl-5-oxo-bicyclo[2.2.2]octane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 85225-59-8 3-(4-Methoxy-phenyl)-2-phenyl-isoxazolidine-5-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 135457-93-1 (1S,5R,6S)-3-Benzyl-8-methyl-2,4-dioxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 135457-93-1 (1S,5R,6R)-3-Benzyl-8-methyl-2,4-dioxo-3,8-diaza-bicyclo[3.2.1]octane-6-carboxylic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 114687-41-1 2-(Pyridin-2-ylsulfanyl)-pentanoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 137441-52-2 C₂₃H₃₂N₂O₃ 
• 128737-36-0 2-(Hydroxy-phenyl-methyl)-acrylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 108893-60-3 3-Hydroxy-2-methylene-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 

Relevant academic research and scientific papers

Addition of Cl2C: To (-)-O-menthyl acrylate under sonication-phase-transfer catalysis. Efficient synthesis of (+)- and (-)-(2-chlorocyclopropyl)methanol

Dichlorocyclopropanation of (-)-O-menthyl acrylate under conditions of phase-transfer catalysis (CHCl3, KOH, tetramethylammonium bromide), with sonication, gives excellent yields (85-94%) of the corresponding dichlorocyclopropanecarboxylate est

Asymmetric organocatalytic cyclopropanation on chiral menthyl acrylate for the synthesis of (-)- trans -2-aminomethylcyclopropanecarboxylic acid [(-)-tamp]

An enantioselective synthesis of (-)-trans-2- aminomethylcyclopropanecarboxylic acid [(-)-TAMP], a partial agonist for GABAc receptor, has been achieved as the hydrochloride salt in 3.9% overall yield for total eight steps from l-menthol. The synthesis fe

Stereoselective synthesis of novel C-3 functionalized 3-sulfonyl-β-lactams: Promising biologically active heterocyclic scaffolds

An efficient and operationally simple strategy for the stereoselective synthesis of novel C-3 functionalized 3-sulfonyl-β-lactam heterocycles is described. The C-3 functionalized 3-phenyl/benzylsulfonyl-β-lactams 3/3′, 5/5′ has been synthesized via Michael addition using different Michael acceptors on trans-3-phenyl/benzylsulfonyl-β-lactams 2(a–f) using K2CO3as a base and acetonitrile/DMF as solvents. The reaction furnished exclusively cis-β-lactam adducts 3(a–r) using sterically less hindered Michael acceptors. Further, the effect of steric bulk and chiralilty of Michael acceptors was explored to achieve target C-3 functionalized β-lactams 3(s-u)/3′(s-u) and 5(a–c)/5′(a–c). The structural and stereochemical analysis of novel β-lactams were carried out using FT-IR, NMR (1H,13C,1H-1H COSY,1H-13C COSY and13C DEPT-135), elemental analysis (CHNS), mass spectrometry (EIMS and LCMS) in representative cases and single crystal X-ray crystallographic studies (3e). The cis or trans configuration of the Michael acceptor (E) at C-3 was assigned with respect to C4-H.

Visible-Light-Induced Trifluoromethylation of Allylic Alcohols

An organic photoredox-catalyzed dehydroxylative trifluoromethylation of allylic alcohols was developed in an environmentally benign manner. In this reaction, the readily available CF3SO2Na was selected as the trifluoromethylation reagent. The in situ generated byproduct SO2 was reutilized to activate C-OH bond, which enabled this dehydroxylative trifluoromethylation to be performed conveniently. A variety of multifunctionalized CF3-allylic compounds were obtained in high yields and excellent stereoselectivity.

Trifluoromethyl allyl compound as well as preparation method and application thereof

The invention discloses a trifluoromethyl allyl compound as well as a preparation method and application thereof. According to the method, allyl alcohol is directly used as a raw material, CF3SO2Na is selected as a trifluoromethylation reagent, a metal-free and cheap photooxidation reduction catalyst is used, and under the catalysis of an organic photooxidation reduction agent, a byproduct SO2 generated in situ is reused as an activated C-OH bond, so that the reaction is carried out in an environment-friendly manner under a mild condition. The allyl alcohol used in the preparation method disclosed by the invention is a MoritA-Baylis-Hillman alcohol allyl alcohol raw material which is simple to synthesize and high in conversion rate, the applicable substrate range is wide, and the preparation cost is low. In addition, the preparation method disclosed by the invention is simple in steps, and has the characteristics of convenience in operation, environment friendliness, excellent stereoselectivity and broad-spectrum functional group tolerance. The trifluoromethyl allyl compound provided by the invention is a general precursor for preparing related CF3 molecules, has potential pharmaceutical activity and biological activity, and can be widely applied to biological and pharmaceutical active molecules.

Late-Stage Macrocyclization of Bioactive Peptides with Internal Oxazole Motifs via Palladium-Catalyzed C-H Olefination

Oxazole is an important pharmacophore and exists in the backbone of many bioactive peptide natural products and peptidomimetics. Efficient methods for the synthesis and direct functionalization of complex oxazole-containing peptides are in high demand. Herein, we report the late-stage site-selective functionalization of oxazole-containing peptides via palladium-catalyzed δ-C(sp2)-H olefination of phenylalanine, tryptophan, and tyrosine residues. This strategy utilizes oxazole motifs as internal directing groups and provides access to oxazole-containing peptide macrocycles with bioactivities.

Acid- And base-switched palladium-catalyzed γ-C(sp3)-H alkylation and alkenylation of neopentylamine

The functionalization of remote unactivated C(sp3)-H and the reaction selectivity are among the core pursuits for transition-metal catalytic system development. Herein, we report Pd-catalyzed γ-C(sp3)-H-selective alkylation and alkenylation with removable 7-azaindole as a directing group. Acid and base were found to be the decisive regulators for the selective alkylation and alkenylation, respectively, on the same single substrate under otherwise the same reaction conditions. Various acrylates were compatible for the formation of C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds. The alkenylation protocol could be further extended to acrylates with natural product units and α,β-unsaturated ketones. The preliminary synthetic manipulation of the alkylation and alkenylation products demonstrates the potential of this strategy for structurally diverse aliphatic chain extension and functionalization. Mechanistic experimental studies showed that the acidic and basic catalytic transformations shared the same six-membered dimer palladacycle.

A Method For Preparing (Meth)Acrylic Acid Ester Based Compound

The invention relates to a method for preparing a (meth)acrylic acid ester-based compound, and according to the preparation method, a (meth)acrylic acid ester-based compound can be prepared with high purity and high yield, by easily introducing an acrylic structure into alcohol using a diamine-based compound and acid anhydride.

Four Stereoisomers of 2-Aminomethyl-1-cyclopropanecarboxylic Acid: Synthesis and biological evaluation

Here, we report a practical method for asymmetric synthesis of cyclopropane-fused GABA analogs. Starting from 2-furaldehyde, the cis-isomer (CAMP) was synthesized over 10 steps; (1)- and (+)-CAMP￠HCl were synthesized by employing d- and l-menth

Photoredox-Coupled F-Nucleophilic Addition: Allylation of gem-Difluoroalkenes

A novel strategy for the expedient construction of CF3-embeded tertiary/quarternary carbon centers was developed by taking advantage of photoredox catalysis. Thanks to a key step of single-electron oxidation, electron-rich gem-difluoroalkenes, which otherwise are essentially reluctant towards F-nucleoplilic addition, now readily participate in this fluoroallylation reaction. Furthermore, this strategy provides an elegant example for the generation, as well as functionalization, of α-CF3-substituted benzylic radical intermediates using cheap and readily available starting materials.