115362-12-4

Basic information

• Product Name: (-)-(2S,3S)-2,3-epoxy-3-cyclohexyl-1-propanol
• Synonyms: (-)-(2S,3S)-2,3-epoxy-3-cyclohexyl-1-propanol
• CAS NO: 115362-12-4
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.22214
• Mol File: 115362-12-4.mol

Chemical Properties

• Boiling Point: 254.8 °C at 760 mmHg
• Flash Point: 107.4 °C
• Appearance: /
• Density: 1.092 g/cm³
• Vapor Pressure: 0.00257mmHg at 25°C
• Refractive Index: 1.51
• CAS DataBase Reference: (-)-(2S,3S)-2,3-epoxy-3-cyclohexyl-1-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(2S,3S)-2,3-epoxy-3-cyclohexyl-1-propanol(115362-12-4)
• EPA Substance Registry System: (-)-(2S,3S)-2,3-epoxy-3-cyclohexyl-1-propanol(115362-12-4)

Safety Data

• Hazardous Substances Data: 115362-12-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Production:
(-)-(2S,3S)-2,3-Epoxy-3-cyclohexyl-1-propanol is used as an intermediate in the production of various chemicals, leveraging its unique structural features and reactivity to synthesize a range of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, (-)-(2S,3S)-2,3-Epoxy-3-cyclohexyl-1-propanol is utilized as a key component in the synthesis of drugs, potentially contributing to the development of new medications due to its specific stereochemistry and functional groups.
Used in Organic Synthesis:
(-)-(2S,3S)-2,3-Epoxy-3-cyclohexyl-1-propanol serves as a valuable building block in organic synthesis, where its epoxy group can participate in various reactions to form a diverse array of organic compounds.
Used in Research:
(-)-(2S,3S)-2,3-Epoxy-3-cyclohexyl-1-propanol is also employed in research settings for studying the properties and reactions of epoxy-containing molecules, furthering understanding in the field of organic chemistry and potentially leading to new discoveries and applications.

InChI:InChI=1/C9H16O2/c10-6-8-9(11-8)7-4-2-1-3-5-7/h7-10H,1-6H2/t8-,9-/m0/s1

Upstream product

• 42134-55-4 (E)-3-cyclohexyl-2-propen-1-ol 
• 42134-55-4 3-cyclohexyl-2-propen-1-ol 
• 142528-81-2 cis S-tert-Butyl 3-cyclohexyloxirane-2-carbothioate 
• 1438398-81-2 C₁₅H₂₅NO₂S 
• 1285721-50-7 C₂₃H₃₃NO₄S 
• 2043-61-0 cyclohexanecarbaldehyde 
• 17343-88-3 (E)-3-cyclohexyl-acrylic acid ethyl ester 
• 4484-35-9 3-cyclohexylacrylic acid 
• 705-95-3 3-cyclohexylacrylic acid methyl ester 

Downstream Products

• 129170-75-8 (1S,2R)-1-cyclohexyl-2-methyl-1,3-propane diol 
• 129065-00-5 (1S,2R)-1-Cyclohexyl-2-vinyl-propane-1,3-diol 
• 461023-63-2 4-[4-(((3S)-1-butyl-3-[(R)-cyclohexyl(hydroxy)methyl]-2,5-dioxo-1,4,9-triazaspiro[5.5]undec-9-yl)methyl)phenoxy]benzoic acid hydrochloride 

Relevant articles and documents

New one-pot procedure for the synthesis of diprotected amino alcohols from unprotected vinyl aziridines

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A highly regioselective azidolysis of 2,3-epoxy amines: An unexpected [Ti(O-i-Pr)2(N3)2] mediated C-2 opening

The Lewis acid-catalysed regioselective azidolysis of 2,3-epoxy amines has been investigated. The results obtained demonstrated that using TMSN3 as a source of azide, the appropriate choice of Lewis acid allowed to direct the regiochemistry of the ring opening. The present methodologies provide a powerful tool in organic synthesis for the preparation of diaminoalcohol moieties.

A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis

A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α-amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans-epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98 %). The obtained epoxy amides were found to be useful as synthetic building blocks. Thus, they were reduced into their corresponding epoxy alcohols and subjected to oxirane-ring-opening reactions with different types of nucleophiles.

Cyclic sulfur ylides derived from gleason-type chiral auxiliaries for the asymmetric synthesis of epoxy amides

Gleason-type chiral auxiliaries were used for the synthesis of a novel class of sulfonium salts, obtained via methylation of the sulfide with Meerwein's salt. The salts were reacted with aldehydes under basic conditions to provide epoxy amides, which were reduced to their corresponding epoxy alcohols in excellent enantiomeric excesses. Interestingly, it was feasible to synthesize both enantiomeric epoxy alcohols depending on which of the sulfonium salts, prepared from L-amino acids (6 and 9 from L-valine or 15 and 16 from L-serine) was employed.

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