155320-76-6

Basic information

• Product Name: (S)-2-METHOXYCYCLOHEXANONE
• Synonyms: (S)-2-METHOXYCYCLOHEXANONE;S-MON
• CAS NO: 155320-76-6
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• Mol File: 155320-76-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 189.3°Cat760mmHg
• Flash Point: 68.8°C
• Appearance: /
• Density: 0.98g/cm³
• Vapor Pressure: 0.574mmHg at 25°C
• Refractive Index: 1.44
• CAS DataBase Reference: (S)-2-METHOXYCYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-METHOXYCYCLOHEXANONE(155320-76-6)
• EPA Substance Registry System: (S)-2-METHOXYCYCLOHEXANONE(155320-76-6)

Safety Data

• Hazardous Substances Data: 155320-76-6(Hazardous Substances Data)

Usage

General Description

(S)-2-Methoxycyclohexanone is a chemical compound with the molecular formula C7H12O2. It is a cyclic ketone with a methoxy group and is primarily used as an intermediate in the synthesis of various pharmaceuticals and fine chemicals. It is also utilized as a flavoring agent and fragrance ingredient in the production of perfumes and cosmetics. The compound is a colorless liquid with a sweet, floral odor and is known for its stability and low toxicity. Its unique chemical structure and reactivity make it a valuable building block in organic synthesis processes, particularly in the pharmaceutical and fragrance industries.

InChI:InChI=1/C7H12O2/c1-9-7-5-3-2-4-6(7)8/h7H,2-5H2,1H3/t7-/m0/s1

Upstream product

• 23740-37-6 2-methoxycyclohex-2-en-1-one 
• 7757-83-7 sodium sulfite 
• 2979-24-0 2-methoxycyclohexanol 
• 121961-00-0 Acetic acid (1S,2S)-2-methoxy-cyclohexyl ester 
• 134070-87-4 trans-2-methoxycyclohexyl butanoate 
• 134108-78-4 Butyric acid (1S,2S)-2-methoxy-cyclohexyl ester 
• 60624-22-8 (+/-)-trans-1-acetoxy-2-methyoxycyclohexane 
• 7429-40-5 trans-2-methoxycyclohexanol 
• 187404-43-9 [Bromo-((1S,2S)-2-methoxy-cyclohexyl)-methyl]-benzene 
• 187404-44-0 [Bromo-((1R,2S)-2-methoxy-cyclohexyl)-methyl]-benzene 
• 187404-42-8 ((1S,2S)-2-Methoxy-cyclohexylmethyl)-benzene 
• 187404-41-7 ((1R,2S)-2-Methoxy-cyclohexylmethyl)-benzene 
• 187404-39-3 (S)-2-[1-phenyl-(E)-methylidene]-1-cyclohexanol 
• 125992-53-2 (1S,2R)-α-benzylcyclohexanol 

Downstream Products

• 135297-22-2 (3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one 
• 1254223-87-4 (S)-N'-(2-methoxycyclohexylidene)-4-methylbenzenesulfonohydrazide 
• 173459-91-1 (S)-6-methoxy-1-(trimethylsilyloxy)cyclohex-1-ene 
• 1005345-21-0 (1S,2S)-2-methoxy-1-((1R)-1-phenyl-allyl)-cyclohexanol 

Relevant articles and documents

Asymmetric bioreduction of alkenes using ene-reductases YersER and KYE1 and effects of organic solvents

Asymmetric trans-bioreduction of activated alkenes by KYE1 from Kluyveromyces lactis and Yers-ER from Yersinia bercovieri, two ene-reductases from the Old Yellow Enzyme family, showed a broad substrate spectrum with a moderate to excellent degree of stereoselectivity. Both substrate- and enzyme-based stereocontrols were observed to furnish opposite stereoisomeric products. The effects of organic solvents on enzyme activity and stereoselectivity were outlined in this study, where two-phase systems hexane and toluene are shown to sustain bioreduction efficiency even at high organic solvent content.

trans-RuH(η1-BH4)(binap)(1,2-diamine): A catalyst for asymmetric hydrogenation of simple ketones under base-free conditions

(Chemical Equqtion Presentation) Reaction of a chiral RuCl2(diphosphine)(1,2-diamine) complex and NaBH4 forms trans-RuH(η1-BH4)(diphosphine)(1,2-diamine) quantitatively. The TolBINAP/DPEN Ru complex has been characterized by single crystal X-ray analysis as well as NMR and IR spectra. The new Ru complexes allow for asymmetric hydrogenation of simple ketones in 2-propanol without an additional strong base. Various base-sensitive ketones are convertible to chiral alcohols in a high enantiomeric purity with a substrate/catalyst ratio of up to 100 000 under mild conditions. Configurationally unstable 2-isopropyl- and 2-methoxycyclohexanone can be kinetically resolved with a high enantiomer discrimination. This procedure overcomes the drawback of an earlier method using RuCl2(diphosphine)(diamine) and an alkaline base, which sometimes causes undesired reactions such as ester exchange, epoxy-ring opening, β-elimination, and polymerization of ketonic substrates. Copyright

Process for the preparation of cyclohexyl-azetidinones

1. A process for the preparation of compounds of formula (I) wherein R1 is a hydroxyl protecting group STR1 which comprises reacting the azetidinone (II) with the homochiral (2S)-2- methoxycyclohexane (III) or the complex thereof formed with on