4335-77-7

Basic information

• Product Name: 2-Cyclohexylmandelic acid
• Synonyms: acidephenylcyclohexylhydroxyacetique;alpha-cyclohexyl-alpha-hydroxy-benzeneaceticaci;alpha-cyclohexyl-alpha-hydroxybenzeneaceticacid;alpha-phenyl-cyclohexaneglycolicaci;alpha-phenylcyclohexaneglycolicacid;hexahydrobenzilicacid;kl-007-m1;lespedamine
• CAS NO: 4335-77-7
• Molecular Formula: C₁₄H₁₈O₃
• Molecular Weight: 234.29
• EINECS: 224-380-4
• Product Categories: Pharmaceutical Intermediates;Aromatics
• Mol File: 4335-77-7.mol
• Article Data: 16

Chemical Properties

• Melting Point: 163 °C
• Boiling Point: 135℃/3mm
• Flash Point: 215.1 °C
• Appearance: White to pale brown/Solid
• Density: 1.206 g/cm³
• Vapor Pressure: 2.08E-07mmHg at 25°C
• Storage Temp.: -20°C Freezer
• PKA: 3.49±0.25(Predicted)
• CAS DataBase Reference: 2-Cyclohexylmandelic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexylmandelic acid(4335-77-7)
• EPA Substance Registry System: 2-Cyclohexylmandelic acid(4335-77-7)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• RTECS: GV2770000
• HazardClass: IRRITANT
• Hazardous Substances Data: 4335-77-7(Hazardous Substances Data)

Usage

Description

This indole alkaloid occurs in the leaves of Lespedeza bicolor var. japonica and, when pure, is a colourless oil. Its MeOH solution, the ultraviolet spectrum exhibits absorption maxima at 223.4, 279 and 291 mJi. The crystalline hydrochloride has m.p. 163-4°C (dec.); the picrate forms long, yellow needles from MeOH, m.p. 160-2°C (dec.) and the styphnate, also yellow needles, has m.p. 170°C (dec.). The structure has been established as 3-(dimethylaminoethyl)-1-methoxyindole.

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 4335-77-7 differently. You can refer to the following data:
1. An intermediate in the synthesis of oxybutynin (O868525).
2. intermediate for Oxybutynin HCl, Oxyphenonium Bromide
3. An intermediate in the synthesis of oxybutynin (O868525). Oxybutynin USP Related Compound A.

References

Morimoto, Oshio., Annalen, 682, 212 (1965)

InChI:InChI=1/C14H18O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1,3-4,7-8,12,17H,2,5-6,9-10H2,(H,15,16)/p-1/t14-/m0/s1

Upstream product

• 31197-69-0 ethyl 2-cyclohexyl-2-hydroxy-2-phenylacetate 
• 76-93-7 Benzilic acid 
• 5633-20-5 oxybutynin 
• 1508-65-2 Oxybutynin chloride 
• 424792-60-9 2-(2'-cyclohexen-1'-yl)-2-hydroxy-2-phenylacetic acid 
• 424792-59-6 methyl 2-(2'-cyclohexen-1'-yl)-2-hydroxy-2-phenylacetate 
• 67-56-1 methanol 
• 151900-28-6 methanol hydrate 
• 931-51-1 cyclohexylmagnesiumchloride 
• 611-73-4 Benzoylformic acid 
• 4441-56-9 cyclohexylboronic acid 
• 446065-11-8 cyclohexyltrifluoro-λ⁴-borane potassium salt 
• 4358-87-6 (RS)-methyl mandelate 
• 626-62-0 Cyclohexyl iodide 

Downstream Products

• 96167-82-7 cyclohexyl-hydroxy-phenyl-acetic acid-(2-piperidino-ethyl ester) 
• 3570-96-5 demethyloxyphenonium 
• 93005-50-6 cyclohexylidene-phenyl-acetic acid 
• 6313-70-8 dicyclohexyl-hydroxy-acetic acid 
• 14657-85-3 Cyclohexyl-phenyl-glykolsaeure-<2-brom-aethylester> 
• 25520-98-3 cyclohexyl-hydroxy-phenyl-acetic acid-(2-dimethylamino-ethyl ester) 
• 128887-53-6 Cyclohexyl-hydroxy-phenyl-acetic acid 3-pyrrolidin-1-yl-propyl ester 
• 128887-54-7 Cyclohexyl-hydroxy-phenyl-acetic acid 3-piperidin-1-yl-propyl ester 
• 128887-55-8 Cyclohexyl-hydroxy-phenyl-acetic acid 3-azepan-1-yl-propyl ester 
• 10399-13-0 methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate 
• 712355-73-2 (1α, 5α, 6α)-6-N-(3-azabicyclo [3.1. 0] hexyl-3-benzyl)-2-cyclohexyl-2-hydroxy-2-phenyl acetamide 
• 405089-66-9 2-Cyclohexyl-2-hydroxy-2-phenyl-1-[3-(4-trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-ethanone 
• 5633-20-5 oxybutynin 
• 1012064-46-8 (3-Benzyl-3-azabicyclo[3.2.1]oct-8-yl)methyl cyclohexyl(hydroxy)phenylacetate 

Relevant articles and documents

Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters

A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.

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SUBSTITUTED PHENYLCYCLOHEXYLGLYCOLATES

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