109527-45-9

Usage

Uses

Used in Pharmaceutical Production:
(1S,2R)-(+)-TRANS-2-(1-METHYL-1-PHENYLETHYL)CYCLOHEXANOL is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique structural properties and chiral center. Its specific stereochemistry is crucial for the development of drugs with targeted therapeutic effects.
Used in Organic Synthesis:
In the field of organic synthesis, (1S,2R)-(+)-TRANS-2-(1-METHYL-1-PHENYLETHYL)CYCLOHEXANOL serves as a valuable building block for the creation of complex organic molecules. Its cyclohexane ring and trans-substituent orientation allow for versatile chemical reactions, facilitating the synthesis of a wide range of compounds.
Used in Research and Development for Therapeutic Applications:
(1S,2R)-(+)-TRANS-2-(1-METHYL-1-PHENYLETHYL)CYCLOHEXANOL is used as a subject of research for its potential therapeutic applications. It has been studied for its analgesic properties, making it a candidate for the development of pain relief medications. Additionally, it has been investigated for its potential in treating substance abuse, offering a new avenue for addiction treatment.
Used in the Synthesis of Natural Products and Related Compounds:
(1S,2R)-(+)-TRANS-2-(1-METHYL-1-PHENYLETHYL)CYCLOHEXANOL has also been studied for its potential use in the synthesis of natural products and compounds related to them. Its unique structure and chirality make it a promising candidate for the development of novel natural product analogs with potential biological activities.

InChI:InChI=1/C15H22O/c1-15(2,12-8-4-3-5-9-12)13-10-6-7-11-14(13)16/h3-5,8-9,13-14,16H,6-7,10-11H2,1-2H3/t13-,14-/m0/s1

Upstream product

• 98-82-8 Isopropylbenzene 
• 286-20-4 cyclohexane-1,2-epoxide 
• 221007-40-5 (R)-4-Oxo-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 1228187-18-5 (2S,5R)-((1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl)tetrahydro-5-((S)-2-trimethylsiloxy-6-methylhept-5-en-2-yl)-2-methylfuran-2-carboxylate 
• 199742-72-8 1-[2-bromo-4,5-dimethoxybenzyl]-2-[((1S,2R)-(1-methyl-1-phenylethyl)cyclohexyloxy)carbonyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 199742-71-7 N-[(1S,2R)-(2-(1-methyl-1-phenylethyl)cyclohexyloxy)carbonyl]-2-(3,4-dimethoxyphenyl)ethylamine 
• 161693-64-7 (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl chloroformate 

Downstream Products

• 161693-64-7 (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl chloroformate 
• 681006-04-2 2-oxo-pyrrolidine-1-carboxylic acid 2-(1S,2R)-(1-methyl-1-phenylethyl)cyclohexyl ester 
• 681006-05-3 2-(2-phenylpropan-2-yl)cyclohexyl-2-oxopiperidine-1-carboxylate 
• 1228187-17-4 (Z)-(1S,2R)-2-(2-phenylpropan-2-yl)cyclohexyl-6,10-dimethyl-2-methyleneundeca-5,9-dienoate 
• 1296196-28-5 (R)-2-(2-phenylpropan-2-yl)cyclohexanone 
• 1361955-11-4 C₁₈H₂₄O₂S₂ 
• 1361955-23-8 (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl 4,5-dimethyl-2-(methylsulfanyl)-3,6-dihydro-2H-thiopyran-2-carboxylate 
• 1361955-39-6 (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl 2-chloroacetate 

Relevant academic research and scientific papers

Dialkoxycarbenes in (4 + 1) Cycloadditions: Application to the Synthesis of Carotol

Dialkoxycarbenes are more reactive than NHCs and participate in many reactions including a formal (4 + 1) cycloaddition with electron-deficient dienes. We have learned to control the relative stereochemistry of the newly created chiral carbons in this pro

Enantioselective formal synthesis of eurylene: Synthesis of the cis - And trans -THF fragments using oxidative cyclization

A formal synthesis of eurylene is described, where both cis- and trans-THF-containing fragments were prepared using diastereo- and chemoselective permanganate-mediated oxidative monocyclizations of trienes.

Asymmetric synthesis of dienomycin C

The first asymmetric synthesis of dienomycin C was accomplished in seven Steps and 46% overall yield.

Chiral auxiliary mediated pictet-spengler reactions: Asymmetric syntheses of (-)-laudanosine, (+)-glaucine and (-)-xylopinine

Cyclohexyl-based chiral auxiliaries can be used effectively in an asymmetric Pictet-Spengler synthesis of tetrahydroisoquinoline, aporphine and protoberbine alkaloids. Using this strategy, concise asymmetric syntheses of (-)-laudanosine, (+)-glaucine and (+)- xylopinine have been accomplished.

An efficient preparation of (+)-trans-2-(α-cumyl)cyclohexanol ((+)-TCC): A practical alternative to (+)-8-phenylmenthol

An efficient synthesis and resolution of trans-2-(α-cumyl)cyclohexanol gives the (+)-enantiomer in three steps from cyclohexene oxide.

Efficient Synthesis and Resolution of trans-2-(1-Aryl-1-methylethyl)cyclohexanols; Practical Alternatives to 8-Phenylmenthol

A short synthesis and resolution of effective chiral auxiliaries of the 8-arylmenthol-type achieved using inexpensive materials, a recyclable lipase, and easily applied procedures that are amenable to large-scale preparation.A variety of isopropylarenes were α-metalated with n-butylithium/potassium tert-pentoxide and treated with cyclohexene oxide to provide racemic trans-2-(1-aryl-1-methylethyl)cyclohexanols 6a-f in fair to high yield.Candida rugosa lipase and lauric acid were used to resolve these racemic alcohols by converting the (-)-enantiomer to its laurateester.The enzymatic resolutions were carried out at 40 deg C and were faster in cyclohexane than in hexanes.The synthesis and resolution of racemic trans-2-(1-methyl-1-phenylethyl)cyclohexanol (6a) were performed on a 1 mol scale in 68 percent overall yield, requiring three steps for (+)-6a and five steps for (-)-6a.

Cycloalkyl-based chiral auxiliaries and method making the same

A process of synthesizing enantiomerically pure compounds defined by Formula V, STR1 which are useful as chiral auxiliaries is disclosed. The process comprises, first, combining a base of Formula Y- Z+ (Formula I), wherein Y- is an organic anion and Z+ is an inorganic cation, with a compound of Formula II, STR2 wherein R1 is a C1 -C4 alkyl group and R2 is the same as R1, or wherein R1 and R2 together form cyclopentane or cyclohexane, and wherein R3 is a substituted or unsubstituted aryl group, to form a compound defined by Formula III, STR3 then: (b) reacting the compound of Formula III with a cyclic epoxide defined by Formula IV, STR4 wherein n is 1, 2, or 3, to form a racemic mixture of a compound defined by Formula V. STR5 In a preferred embodiment, the method further comprises stereospecifically esterifying one of the enantiomers of the racemic mixture of compound (V) and a carboxylic acid with an enzyme in an organic solvent, wherein said acid is a C2 -C20 alkyl acid, benzoic acid or a C2 -C14 alkyl benzoic acid, and then separating the esterified enantiomer from the non-esterified enantiomer.